northeast us travel itinerary

Kate Abroad

The Ultimate 10 Day Northeast USA Itinerary (+ 1 and 2 week options)

Thinking of visiting the Northeastern Region of the USA? Look no further than this 10 day Northeastern USA travel itinerary.

The Northeast region of the United States is a beautiful and historically rich area that offers a ton of unique travel experiences. Whether you’re interested in exploring bustling cities, enjoying the great outdoors, or soaking up some American history, there’s something for everyone in the Northeast.

With so many incredible destinations to choose from, planning the perfect itinerary can be overwhelming. But don’t stress, in this guide, I’ll walk you through the process of planning your Northeast USA travel itinerary. We’ll cover all the must-see destinations, the best times to visit, and plenty of tips to help you make the most of your trip.

From the stunning fall foliage in New England to the towering skyscrapers of New York City, the Northeast has it all. Whether you’re a history buff, a foodie, or an outdoors enthusiast, the Northeast is sure to exceed your expectations. So block out your calendar and get ready to explore the very best that the Northeastern USA has to offer!

First a note: these itineraries all start in New York because for international travellers that’s typically the cheapest place to fly in and out of with the most airports and flight options. However, if you’re already in the USA or not concerned about flight costs, it would make sense to start at Boston (the northernmost point on the itinerary) and work your way south or vice versa.

How to get around the Northeastern USA

This itinerary is designed so that you can do it either as a 10 day Northeast USA road trip or travel by bus or train if you prefer not to drive. I’ve personally done it both ways and can tell you the trains are the easiest and most affordable way to get around in the Northeast.

All of the destinations on these itineraries (including the 1 and 2 week options) are along Amtrak’s Northeast Regional train route so you don’t even need to worry about train connections. Most trains stations in the Northeast are right in the center of each city, so you can walk straight off the train and start exploring.

The 10 Day Northeast USA road/train trip itinerary

Days 1-3: new york.

There’s no better place to start a USA road trip than the Big Apple, the concrete jungle where dreams are made of…. While you can (and I have) easily spend a week or more in NYC, 3 days is a good amount of time to see the highlights and get a taste.

It can be overwhelming to know where to start so to make it easy I recommend dedicating one day to each of Midtown and Downtown Manhattan and Brooklyn.

Day 1 – Midtown Manhattan: Start your day in Times Square, the bustling heart of Midtown Manhattan. There’s no better place to take in the bright lights and energy of the city. Here, you can shop at the many stores and boutiques (don’t miss the 3 storey M&Ms store) and grab breakfast or coffee at one of the many cafes.

From there, head to the  Empire State Building , where you can take in breathtaking views of the city from the observation deck. Next, visit the iconic Grand Central Terminal, one of the busiest train stations in the world and a beautiful example of Beaux-Arts architecture.

End your day with a visit to Central Park, the iconic park that spans 843 acres in the heart of Manhattan. Here, you can have a picnic, go for a jog, rent a boat, or simply relax and people watch. It’s not advised to do a carriage ride as some horses may be mistreated.

Day 2 – Downtown Manhattan: Start your day in Battery Park, where you can catch a ferry to the Statue of Liberty and Ellis Island. You have the option of either the free Staten Island Ferry that goes past Liberty Island or the  paid Statue Cruises that lets you get off on Liberty Island, I’ve done both and the paid version is worth the money.

Afterward, take a stroll through the historic Financial District, where you can see the New York Stock Exchange, the Charging Bull statue, and the extremely moving 9/11 Memorial.

If you’re keen for more views you can head up the One World Trade Center Observatory, the tallest building in the Western Hemisphere.

End your day with a stroll through the trendy neighborhoods of SoHo and Greenwich Village, where you can shop, dine, and people-watch to your heart’s content.

Day 3 – Brooklyn and Uptown: On the last day in NYC, make your way across the Brooklyn Bridge, walk around the waterfront with its panoramic views of the Manhattan skyline, get your photos in DUMBO and eat your way through Time Out Market.

If you have extra time, explore the Brooklyn Botanic Garden or visit the Brooklyn Museum, which houses an impressive collection of art and artifacts from around the world.

Then spend the afternoon taking in thousands of years of art at The Met and seeing how the other half live on the Upper East Side.

From there, take a subway ride up to Harlem, where you can explore the neighborhood’s rich cultural heritage, visit the famous Apollo Theater, and grab dinner at one of the many soul food restaurants.

To help save money on attractions, try a  Go City pass . They have 2 and 3 day all-inclusive passes that would be perfect for this itinerary –  click here to see how you can save .

Finally, don’t forget to make time for plenty of pizza slices, bagels, pretzels and hot dogs!

• Luxury:  Kixby
• Mid-range:  Hotel Indigo Downtown
• Budget:  HI USA Hostel

Click here to compare NYC accommodation prices on Booking.com

Day 4-5: Boston

Drive: 220 miles – approx. 3.5 hours

Train: Amtrak Northeast Regional from Moynihan Train Hall – approx. 4 hours

After the craziness of New York, head up north to the relative calm of Boston, Massachusetts. Boston is a city steeped in history and culture but despite its historic nature the crazy number of universities in Boston means the city has a very young, fun vibe. With world-class museums, delicious food, and beautiful parks, there’s something for everyone in this vibrant city.

Start your trip with a walk along the Freedom Trail, a 2.5-mile route that takes you through some of Boston’s most important historic sites, including the Massachusetts State House, Paul Revere’s House, and the USS Constitution Museum. Along the way, you’ll learn about the events leading up to the American Revolution and the role Boston played in shaping the country’s history.

There are plenty of  walking tours available  but I’d recommend just downloading an audio guide for the Freedom Trail and going at your own pace. And don’t miss the Boston Public Library, it might not be on the Freedom Trail but it was my favourite spot.

Next, head over to the Museum of Fine Arts, where you can explore over 450,000 works of art from around the world. The museum’s collections range from ancient artifacts to contemporary art, and there’s something for every taste and interest.

If you’re a sports fan, make sure to catch a game at Fenway Park, home of the Boston Red Sox. And if baseball isn’t your thing, try an ice hockey game, I can promise it will make for a memorable experience.

For foodies, Boston is a paradise with both fresh New England seafood and quality Italian cuisine on offer. Make sure to try the city’s signature clam chowder and lobster rolls as well as Boston cream pie (go to Omni Parker House for the original version), and cannoli from Mike’s Pastry or Modern Pastry in the North End.

Finally, take a stroll through the beautiful Boston Common, the oldest public park in the country. With over 50 acres of green space, the park is the perfect place to relax and enjoy the city’s natural beauty.

On your second day in Boston, head out to Cambridge to see the Harvard campus (students run  walking tours ) and try some of the fun student bars.

If you have extra time, you can take the train out to Salem to explore the witchy museums and filming locations. It’s only a short ride from North Station or you can take a  day tour from Boston . 

• Luxury:  The Liberty Hotel
• Mid-range:  Revolution Hotel
• Budget:  Found Boston Common

Click here to compare Boston accommodation prices on Booking.com

Day 6: Providence/Newport

Drive: 50 miles – approx. 1 hour

Train: Amtrak Northeast Regional from Back Bay or South Boston and local bus to Newport – approx. 2 hours total

Rhode Island, the smallest state in the USA, might not be on every Northeast itinerary but it’s very much worth a visit.  

Providence itself is quite a small town with a very compact city centre. There are a couple of decent things to do in Providence itself, including visiting the Rhode Island State Capitol – unlike the one in DC, here you’re allowed to just wander around at will and see all the rooms – and the Brown University campus.

However, the number one reason for coming to Providence is because it’s the gateway to Newport, which you’ll want to dedicate most of the day to seeing. 

Newport is a beautiful seaside town full of cute boutiques and restaurants, but its biggest draw is the Gilded Age mansions.  These homes are straight out of The Great Gatsby, offering a glimpse into the opulent lifestyles of America’s wealthiest families during the late 19th and early 20th centuries.

These grand estates are designed to feel very like European palaces with grand ballrooms, ornate gardens, and stunning ocean views. You can tour these mansions and learn about the families who lived there, including the Vanderbilts, Astors, and Morgans. I recommend picking 2-3 and using the audio tours which are included with your tickets and are super informative.

While you’re in Newport check out the Cliff Walk, a stunning (but windy) hike along the ocean. Warm up afterwards with a hot chocolate or some of the famous New England clam chowder.

• Luxury:  The Beatrice
• Mid-range:  Graduate Providence
• Budget:  Courtyard by Marriott Providence Downtown

Click here to compare Providence accommodation prices on Booking.com

Days 7-8: Philadelphia 

Drive: 300 miles – approx. 4.5 hours

Train: Amtrak Northeast Regional from Providence – approx. 5.5 hours

When in Philadelphia, the must-visit attraction is Independence Hall, where both the Declaration of Independence and the US Constitution were signed. To visit, you’ll need to book tickets through the National Parks website several weeks (ideally months) in advance of your trip as numbers are strictly limited and security is tight.

Even if you miss out on tickets to Independence Hall you can still line up to go see the Liberty Bell across the street and wander through the remains of George Washington’s house.

Next head across town to another of Philadelphia awesome free attractions, the Philadelphia Museum of Art. This beautiful neoclassical building boasts works from van Gogh and Monet, among many many others.

Finish the day with a visit to the Eastern State Penitentiary, one of the most famous and haunted prisons in the world. The prison’s notable inmates, include Al Capone and the bank robber “Slick Willie”. If you’re brave enough, sign up for the night tour to discover the spookiest stories from the prison’s history.

Start your second day in Philadelphia with a visit to the Museum of the American Revolution , where you can learn about the events leading up to the American Revolution and the impact it had on the country and the world. The museum features interactive exhibits, including a replica of a colonial-era privateer ship and Goerge Washington’s tent. We enjoyed the short talks from the educators explaining the artefacts in each room.

If you’re a really dedicated fan of America history you can also head over to the Betsy Ross House, where the first American flag was allegedly sewn and take a guided tour of the house to learn about the life of Betsy Ross and the history of the flag.

For lunch head to the Reading Terminal Market, one of the oldest and largest public markets in the country. This is a food’es paradise and the place to go to try local dishes including Philly cheesesteaks, Pennsylvania Dutch pretzels, and Amish donuts.

If you haven’t succumbed to a food coma then spend the rest of the day strolling through the historic district and waterfront, where you can see many other historic sites, including Franklin Court, site of Benjamin Franklin’s home.

• Luxury:  The Franklin on Rittenhouse
• Mid-range:  The Warwick Hotel Rittenhouse Square
• Budget:  Apple Hostels of Philadelphia

Click here to compare Philly accommodation prices on Booking.com

Days 9-10: Washington DC

Drive: 150 miles – approx. 2.5 hours

Train: Amtrak Northeast Regional from Philadelphia 30 th  Street – approx. 2 hours

There’s no better place to wrap up your vacation in the Northeast United States than in the nation’s capital: Washington, D.C.

One of the best things about visiting D.C. is how much you can do for free. The city is home to countless museums, galleries, monuments, and historic buildings that are open to the public.

However, one important piece of advice: it’s essential to plan ahead and book your visits. Many places will book out months in advance, and even those that allow some walk-ins will often require you to spend a long time queuing outside which is no fun in the heat/wind/rain.

If you’re hoping to tour the White House, don’t expect it to be easy. The booking process requires US residents to apply through their local congressman process. The White House website suggests that foreigners can apply through their embassy, but we found that our embassies weren’t even taking bookings.

The Capitol, on the other hand, is much easier to get into, you do need to book but they can get large numbers of visitors through in a day so it’s not hard to get tickets. The Capitol is a must-do. You can’t see in the actual Senate or House chambers but the beautiful rotunda and National Statuary Hall are well worth it in themselves, we loved seeing the statues each state had chosen to donate.

Continuing on the must-see attractions in D.C., walking along the National Mall is a must. This beautiful parkland features the Washington Monument, Lincoln Memorial, and a variety of other monuments and memorials.

If you’re an art lover, don’t miss the National Gallery. This beautiful museum houses tons of amazing artworks including one by Leonardo Da Vinci. Whatever your interests, D.C. is sure to delight and inspire you with its wealth of cultural and historic offerings.

• Luxury:  Eaton DC
• Mid-range:  Lyle DC
• Budget:  Hotel Harrington

Click here to compare DC accommodation prices on Booking.com

Alternative: 1 week Northeast USA itinerary 

This shortened itinerary is very action-packed, suited to fast-paced travellers and those who want to see as much as possible in one trip. 

• Philadelphia
• Washington DC

Alternative: 2 week Northeast USA itinerary 

This extended itinerary fits even more in, while also allowing some extra time in the top destinations for those who prefer to take things at a slower pace. 

• Providence/Newport

Frequently Asked Questions About Visiting Northeastern USA

True to the name, the Northeast covers the area from the Canadian border in the North down to (depending on who you ask) Washington DC on the Virginia border and inland as far as the Ohio border including 11 states.

To avoid the summer crowds and the freezing Northeastern winters, the best time to visit is in late spring (May-June) and early fall (October-November), these are also good times to catch the cherry blossoms or the fall foliage respectively.

For a first-time visitor, 10 days is enough time to see the highlights of the American Northeast but if you can stay a full 2 weeks you’ll get to see even more.

In Short: 10 Days in the Northeastern USA

It’s hard to narrow down the best parts of the Northeast to a short itinerary as there’s so much to see and do and there’s no wrong way to see this part of the USA. Hopefully, these Northeast USA itineraries give you some inspiration to get started!

For more USA travel inspiration, check out these articles:

• East Coast Road Trip Itinerary
• One Week in Los Angeles Itinerary
• Best Midwest Holiday Destinations

Happy travelling!

USA Travel Resources

• Find the best prices on hotels with flexible cancellation at Booking.com
• Find tickets for attractions and awesome day tours on Viator
• Save $$$ on attractions in NYC, LA, Miami and more with a Go City Pass
• Compare prices on cars and campervans at RentalCars.com
• Sort your US dollars with a Wise currency card

Kate is the founder of Kate Abroad. She has travelled to nearly 40 countries from Austria to Vanuatu, and lived in 3. She's on a mission to empower other Gen Zs and Millenials travel affordably by sharing helpful travel guides, stories and tips to over 200,000 readers.

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Northeastern US Routes

10 Top Road Trip Routes in the Northeastern US

The United States abounds with scenic routes and picturesque drives , but the beauty of the Northeast offers landscapes you can't see anywhere else in the country. Chasing rivers and scaling mountains, they wind through the country's most adorable small towns and along its most storied coastline. As the East Coast is famous for its fiery autumn colors, many of these trips are especially striking during the fall . However, each season offers something uniquely enjoyable and you can enjoy these drives at any time of the year.

Read on to find inspiration for your next Northeast road trip.

Upper Delaware River Valley

If you've seen those car commercials that show a slick vehicle navigating a wildly undulating mountain road, there's a good chance it was State Route 97 in the Upper Delaware River Valley of Upstate New York. This twisting highway traces the Delaware River, which forms a natural border between New York State and Pennsylvania. The most famous part is a section known as the Hawk's Nest, which covers the 70 miles from Point Jervis to Hancock. It takes about an hour and a half to complete the route, so even though it isn't the fastest way to travel between the cities, it's undoubtedly the prettiest.

Apart from the stomach-churning turns and breathtaking views, travelers should also stop at landmarks along the route including the Minisink Battleground Park , which hosted a skirmish during the Revolutionary War, and Roebling's Delaware Aqueduct , a canal bridge and engineering marvel built in 1848.

Letchworth State Park

Letchworth State Park in Upstate New York has been nicknamed the "Grand Canyon of the East" for its dramatic gorge that drops 600 feet into the Genesee River below. The best place to get into the park is at the southern entrance in the town of Portageville, which is just over an hour from either Rochester or Buffalo . You can drive the length of the entire park and come out at the north end, which isn't even 20 miles long. But factor in plenty of time for pulling over, taking pictures, and hiking around the gorge. You'll see plenty of waterfalls during your trip through Letchworth, but if they leave you wanting more, Niagara Falls is just an hour and a half away by car.

The Adirondacks

TripSavvy / Lauren Breedlove

In the remote northeastern part of New York's Adirondack Park , there are 46 rounded peaks that soar roughly 4,000 feet or more toward the sky, but you don't need to hike them for glorious views. This scenic drive starts in North Creek, New York—about an hour and a half north of Albany. From North Creek, drive on Route 28N as it loops around through the forest and mountains. Once you reach Blue Mountain Lake, Route 28N turns into Route 28S, but continue weaving through the many charming lakes until you reach Old Forge. The entire route is nearly 90 miles and has plenty of opportunities for stopping the car and enjoying nature.

Along the way, allow time for a scenic Gondola Skyride at Gore Mountain. And don't miss the splendid Adirondack Experience, The Museum on Blue Mountain Lake , a sprawling complex that brings to life the people who've explored, settled, and cherished this wilderness. It's one of the top things to do in New York State .

The Vermont Shore

Yes, Vermont has a coast: a freshwater one along Lake Champlain. And the town of Shelburne—just a few miles south of Burlington —is a picturesque spot to start a drive that affords fabulous views of the lake and its majestic backdrop, the Adirondack Mountains across the border in New York.

Start at ​ Shelburne Farms , a 1,400-acre working farm built on Lake Champlain as a model agricultural estate in the late 19th century. Pick up Route 7 South to Mount Philo State Park  in Charlotte, where you can drive to the summit for panoramic lake views. Continue on Route 7 South to Route 22A through Vergennes and out to Button Bay State Park . Once there, you can hike along a bluff overlooking Lake Champlain or even rent a boat and get out on the water. Not including time out of the car, the drive should take just about an hour.

The Mohawk Trail

Massachusetts Office of Travel and Tourism

A path blazed by five Native American tribes became New England's first official scenic route in 1914. Automobiles have come a long way since then, but the 63-mile Mohawk Trail—Route 2 between Williamstown and Athol in Western Massachusetts —still leads to bucolic scenes that seem little altered over the past century. Famous for its sharp Hairpin Turn, which looks out over the Hoosac Valley, it's a drive you'll particularly want to savor in the fall . Allow time to hike a portion of the Mahican-Mohawk Trail that runs through the Mohawk Trail State Forest in Charlemont. It follows the original footpath trod by New England's earliest inhabitants.

The Kancamagus Highway

New England's ultimate scenic route—especially in the fall—is the 34.5 miles of Route 112 between Conway and Lincoln, New Hampshire. Known by its Native American name, the Kancamagus Highway (pronounced kank-ah-MAU-gus but called "the Kanc" by locals) was completed in 1959, connecting these towns on the east and west sides of the 800,000-acre White Mountain National Forest . There are overlooks, hiking opportunities, historic sites, and campgrounds along this famed roadway, but even if you just motor through (be prepared to ride your brakes when fall traffic peaks), you'll be thrilled by the views of densely forested mountains and the boulder-strewn Swift River.

Connecticut's National Scenic Byway

Think of this as your "serenity now" route. Connecticut's first National Scenic Byway—Route 169 from North Woodstock to Lisbon—is a supreme leaf-peeping route that glides for 30 miles past farmlands, stone walls, and nearly 200 homes built before the Civil War. Worthy stops on your trip include Historic New England's Roseland Cottage in Woodstock, Mashamoquet Brook State Park in Pomfret for lore and hiking, and Martha's Herbary in Pomfret for aromatic gifts. Time your drive to coincide with the Brooklyn Fair , the oldest continuously-held agricultural fair in the U.S., which takes place in late August each year.

Narragansett Bay

Kim Knox Beckius

Set your GPS for 1460 Ocean Road, Narragansett, Rhode Island, and begin this road trip at one of New England's prettiest lighthouses: Point Judith Lighthouse . Although you can't venture inside, you can stroll the grounds of this still-active beacon built in 1857. From here, you'll follow Ocean Road north to Narragansett Town Beach , where surfers ride vigorous waves year-round. The Towers —all that remains of the Gilded Age Narragansett Pier Casino—provide an enchanting backdrop. Drive Route 1A North, and you'll pass Historic New England's Casey Farm , established in 1750 and still operating and open for tours.

From there, take Route 138 East across the Jamestown Bridge, exit onto Conanicut Island, and follow local roads south to Beavertail State Park on Beavertail Road. Here, you'll see the 1856 stone Beavertail Lighthouse and you can venture inside the museum in the assistant keeper's house. Look east, and you'll bring your lighthouse count up to three: Castle Hill Light is visible in the distance.

Massachusetts' Coastline

If you're a fan of fried clams, lobster, and fresh fish, this is the road trip for you. It starts in Gloucester, Massachusetts —the oldest seaport in the U.S.—and follows Route 127A to Route 127 along the coast north of Boston . It then turns inland toward Essex on Route 133 and north once again on Route 1 to Newburyport . Along the way, you'll see Gloucester's Good Harbor Beach, one of the prettiest in New England, and the petite fishing village of Rockport, where the art scene thrives.

You'll be distracted at practically every turn by seafood shacks, but you may want to save your appetite for Essex, where fried clams were invented by Chubby Woodman. His descendants still prepare them the same way at Woodman's of Essex , and some say the golden beauties at The Clam Box up the road in Ipswich are even better, so you'll want to try both. If you're still hungry when you reach Newburyport, finish with a scenic drive along Plum Island, stopping at the no-frills but delicious Bob Lobster on the way. The entire drive is about 45 miles.

Acadia's Park Loop Road

www.cfwphotography.com/Getty Images

The 27-mile Park Loop Road through Maine's Acadia National Park is as exhilarating a drive as you'll find anywhere. Even though it's not a long route, expect to spend at least three to four hours driving, including stops to get out and enjoy the scenery (it can be even longer during the busy summer months due to traffic). The Atlantic waves crashing against the forests make for a truly dramatic landscape, made all the better by the towering Cadillac Mountain—and you can drive to the summit. This national park does charge an entrance fee, but your admission is good for seven days of visits, so make the most of your visit by staying nearby or even camping in the park.

The Mohawk Trail Association. "More Than a Trail... A Journey." Accessed September 11, 2022.

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Unforgettable New England road trip

• Post last modified: May 19, 2024

Planning a road trip through New England ? Get to the heart of the United States ‘ most idyllic corner with this ultimate itinerary, where soothing nature, delightful towns and proud tradition abound. Buckle up — here are all the gems you don’t want to miss.

Disclosure: All listings are independently selected. If you buy something through our links, we may earn an affiliate commission. Learn more ›

New England route

• Start: Boston
• North Conway
• North Adams
• Stockbridge
• Finish: Boston

Begin with a salty trip up along New England’s coast, where Portland, Camden and Acadia NP are highlights. While Interstate 95 is usually quicker, consider sticking to the parallel, more scenic Route 1.

Then, the character of the itinerary changes dramatically. Head west to see the White Mountains, Green Mountains and Berkshires, with the lofty scenery peaking along the iconic Kancamagus Highway.

Back on the coast, explore Mystic, Newport and Cape Cod. Home to Cape Cod National Seashore, Cape Cod provides some of America’s best beaches, making for the perfect finish to your epic drive.

Isn’t Boston the optimal starting point for you? Feel free to start the loop at the location that suits you best.

• Total distance: 1,213 mi / 1,952 km
• Total driving time: 25 h

1. Boston, MA

Massachusetts ‘ largest city, Boston is certainly a convenient place to begin a Northeast road trip. There’s the well-connected Logan Airport and an array of rental car companies to choose from.

But — most of all — Boston is a fun city to explore before you get deeper into the New England itinerary.

If one thing to do in Boston is mandatory, it’s the Freedom Trail . Walking the 2.5-mile (4 km) path, which presents top historic sites in the heart of Boston, is a one-of-a-kind activity.

After touring Boston, you don’t have to like baseball to enjoy a visit to Fenway Park. In all honesty, many visitors don’t even know the baseball rules when they enter Fenway Park for the first time.

However, baseball is an American tradition, and the Red Sox is the team in Boston. Catching a game and feeling the atmosphere at Fenway Park is a memorable experience before heading north — baseball fan or not.

More info: Where to stay in Boston

2. Portland, ME

• Driving distance:  112 mi / 180 km
• Driving time:  2 h

On Maine’s southern coast, Portland offers a lot for anyone looking for a good time.

In particular, the historic Old Port — characterized by cobblestone streets, red-brick buildings, quaint wharves and fishing piers — is the crown jewel. While its facades remind you of past glory days, the district is a modern-day gold mine with eclectic boutiques, watering holes and restaurants.

Capturing at least one of the many lighthouses in the Portland area is also a must, and especially one stands out: Portland Head Light was completed in 1791, making it Maine’s oldest lighthouse.

3. Camden, ME

• Driving distance:  81 mi / 130 km
• Driving time:  1 h 45 min

Countless scenic towns hug Route 1. Camden may be the most picturesque of them all.

Picture a small town lacing an Atlantic cove (Penobscot Bay) with steep slopes (Camden Hills). If you’re short on time, stretch your legs while you browse the stores on the timeless Main Street or sit down in the Camden Amphitheater, a small oasis facing the harbor.

With more time, hike into the rising Camden Hills State Park. But if you don’t want to work for it, you can also drive up to the top of Mount Battie, brilliantly capturing the scenery.

4. Acadia NP, ME

• Driving distance:  77 mi / 124 km

Welcome to the only national park in New England, Acadia. Calling Mount Desert Island home, it encompasses some of the Atlantic’s most untamed coastline — this is one of the most beautiful places in the US .

Although you find awe-inspiring nature all over the island, the eastern half of Mount Desert Island holds most of the park’s star attractions.

An unrivaled eastern highlight is Cadillac Mountain. The views of Acadia are just spectacular from Cadillac Mountain’s summit, both the tallest point of the park and the USA’s eastern seaboard.

Cadillac Mountain peaks at sunrise and sunset but is a beautiful experience throughout the day.

On Mount Desert Island’s quieter western half, another photogenic spot not to miss is Bass Harbor Head Lighthouse. Built in 1858 on the island’s southern tip, it’s not quite as old as Portland Head Light — but no less pretty.

More info: Where to stay near Acadia NP

5. North Conway, NH (White Mountains)

• Driving distance:  212 mi / 341 km
• Driving time:  4 h 15 min

New Hampshire ‘s White Mountains region is filled with great things to do, boasting both stunning natural beauty and cozy towns to relax in.

A shining example of the latter, North Conway is the perfect White Mountains gateway when you come from the east. From here, you effortlessly reach many highlights in the dense White Mountain National Forest.

Within a few miles, Diana’s Baths Cascade — a series of waterfalls dropping 75 feet (23 m) — is a spellbinding place. Another nearby stop is Cathedral Ledge Lookout, offering White Mountains vistas destined for Instagram fame.

When traveling further west, you unlock even more of the White Mountain National Forest.

Driving the famous Kancamagus Highway — one of New England’s most scenic drives — is a jaw-dropping experience. As it runs from Conway to Lincoln, it also takes you right to your next base on the itinerary.

6. Lincoln, NH (White Mountains)

• Driving distance:  41 mi / 66 km
• Driving time:  1 h

Ready for more gorgeous terrain? At the end of the scenic Kancamagus Highway, Lincoln is a practical White Mountains gateway for highlights in the western part of White Mountain National Forest.

The Flume — a natural gorge offering a scenic pool, stunning waterfalls and, of course, mesmerizing White Mountain views — was discovered in 1808 by Jess Guernsey. She came upon it by accident while fishing in the Lincoln area.

After the finding, as the story goes, Jess first had trouble convincing her family about the discovery. It just sounded too magical to be true — but the rest is history.

Today, the Flume is a highlight in Franconia Notch State Park. You find a good variety of hiking trails in Franconia, letting you explore the White Mountains and its dense forests, stunning lakes and majestic peaks further.

7. Stowe, VT (Green Mountains)

• Driving distance:  85 mi / 137 km

A Vermont village with a postcard-worthy downtown area, Stowe sits at the foot of the Green Mountains.

Just strolling down Main Street in Stowe is an appreciated thing to do. It’s a small town, but thanks to its peaceful aura, a walk couldn’t be more rewarding.

When visiting Stove, you’re never far from fresh air and beautiful views. Stowe Recreation Path provides a convenient way to explore Stowe and the village’s lovely surroundings.

Walk, run or bike the paved trail — just be prepared that you will want to stop to take pictures.

Not in Stowe, but just a short drive away, you find the ice cream lover’s dream. Be careful so you don’t get a brain freeze at the original Ben & Jerry’s ice cream factory in Waterbury.

Extra stop: Consider stopping in Burlington, VT, a fun city on the shore of Lake Champlain. Because it’s just 36 miles (58 km) between Stowe and Burlington, you can easily include both on your New England itinerary.

8. North Adams, MA (The Berkshires)

• Driving distance:  159 mi / 256 km
• Driving time:  3 h 15 min

It’s the rolling hills and captivating culture that define The Berkshires region. Marking its northern end, where Vermont meets Massachusetts, North Adams is a great place to start exploring.

Be inspired by evocative galleries and performances at the Massachusetts Museum of Contemporary Art, set on the Hoosic River in downtown North Adams.

Or, simply cruise onwards, letting the peaceful landscape wash over you. North Adams sits along the Mohawk Trail, one of New England’s most scenic drives, finishing in nearby Williamstown.

9. Stockbridge, MA (The Berkshires)

• Driving distance:  35 mi / 56 km

America’s favorite illustrator, Norman Rockwell called Stockbridge home for 25 years. Here, with hundreds of original works, the Norman Rockwell Museum honors and showcases his legacy.

Before Rockwell, the writer Edith Wharton lived in the Berkshires, too. Visit her historic Lenox residence, the expansive Mount Home (maybe on your way from North Adams to Stockbridge), to learn and absorb the idyllic setting.

These are cultural treasures, but don’t forget that what makes the Berkshires outstanding is the mix of culture and nature.

For hiking, a beautiful spot is October Mountain State Forest . At roughly 16,500 acres, it’s Massachusetts’ largest state forest, offering both easy and strenuous trails.

More info: Where to stay in The Berkshires

10. Mystic, CT

• Driving distance:  127 mi / 204 km
• Driving time:  2 h 15 min

On the Connecticut coast, the village of Mystic peacefully sits. Get ready to discover its proud history as a waterside community and center for shipbuilding.

By the Mystic River, Mystic Seaport Museum is one of the USA’s leading maritime museums, preserving an array of seafaring artifacts. Enjoy an impressive collection covering 19 acres, with four National Historic Landmark vessels as the biggest draws.

Compact Historic Downtown Mystic has you covered for authentic shopping, diverse eateries and charming waterfront views. Especially pay attention to the Mystic River Bascule Bridge, a still-in-use drawbridge — nowadays a rare sight.

Extra stop: An alternative to Mystic or an additional stop on the itinerary is New Haven, CT, the home to the famous Yale University.

11. Newport, RI

• Driving distance:  48 mi / 77 km

The shore of Rhode Island is an essential ingredient on your New England road trip itinerary. On Aquidneck Island, Newport is an old colonial city with attractions covering a wide spectrum.

Walking the renowned Newport Cliff Walk, 3.5 miles (5.6 km) long, is a beautiful way to appreciate the Atlantic coast. Tracing Newport’s rocky coastline, it offers stunning natural scenery and fresh salty air.

As a bonus, eye-popping mansions frame the trail.

For the full experience, take a Newport Mansion tour to see how America’s wealthiest and most influential families used to live. The Breakers stands out for its extreme luxury, but the Elms and Marble House are also impressive.

More info: Accommodation in Newport, RI

12. Cape Cod, MA

• Driving distance:  120 mi / 193 km
• Driving time:  2 h 30 min

These 120 miles (193 km) take you all the way to the northern tip of Cape Cod , a peninsula separated from the mainland by the Cape Cod Canal since 1914. Be sure to make plenty of stops along the way.

Cape Cod Rail Trail, excellent for walking or biking, presents a healthy way to sightsee. Paved and extending for 25 miles (40 km) from South Yarmouth to Wellfleet, it follows the 19th-century rail lines that used to carry tourists to Cape Cod.

At the trail’s end, the landscape of Cape Cod National Seashore takes over. Hang out on the seemingly never-ending beach — seals thrive in the waters here — or hike around marshes and ponds.

The finish every peninsula should have, Race Point Beach, as far north as you get, is a phenomenal beach with huge sand dunes. On a sunny day, you might ask yourself: Is this Massachusetts or Florida?

More info: Best areas in Cape Cod

13. Boston, MA

• Driving distance:  116 mi / 187 km

It’s time to round off your unforgettable New England road trip. The last leg is the drive back to where the adventure started, Boston. From the isolated Provincetown, it’s 116 miles (187 miles) to Boston, but it’s shorter if you base yourself elsewhere on Cape Cod.

Where to stay when you road trip through New England

New England takes pride in its atmospheric, often historic inns. Consider making your road trip even better by booking one of our favorite places to stay on Cape Cod.

Appreciate the English Country style at the Old Harbor Inn , a luxurious bed and breakfast set in Chatham. Each of the twelve rooms is unique and the location spot-on for day trips across Cape Cod.

Or, stretch your budget by staying at the Breakwater Hotel , slightly outside Provincetown, at Cape Cod’s northern tip. Drive 5 minutes or walk 30 minutes to get to Provincetown’s heart.

New England itineraries with days

For the full New England road trip, we recommend allowing at least 3 weeks. If you have less time, it’s a good idea to break up the itinerary to focus on your favorite parts.

Ultimate itinerary (3 weeks)

• Day 1-3: Boston (2 nights)
• Day 3-5: Portland (2 nights)
• Day 5-8: Acadia NP (3 nights)
• Day 8-10: North Conway (2 nights)
• Day 10-12: Lincoln (2 nights)
• Day 12-14: Stowe (2 nights)
• Day 14-15: The Berkshires (1 night)
• Day 15-16: Mystic (1 night)
• Day 16-18: Newport (2 nights)
• Day 18-21: Cape Cod (3 nights)

2 week road trip (Atlantic coast)

• Day 1-2: Mystic (1 night)
• Day 2-4: Newport (2 nights)
• Day 4-7: Cape Cod (3 nights)
• Day 7-9: Boston (2 nights)
• Day 9-11: Portland (2 nights)
• Day 11-14: Acadia NP (3 nights)

7 day road trip (Mountain trip)

• Day 1-4: White Mountains (3 nights)
• Day 4-6: Green Mountains (2 nights)
• Day 6-7: The Berkshires (1 night)

New England road trip FAQ

This ultimate New England road trip is 1,213 miles (1,952 km) long, taking 25 hours excluding the time you need for the stops along the way.

The journey includes six states: Massachusetts, Maine, New Hampshire, Vermont, Connecticut and Rhode Island.

The main stops on the itinerary are Boston, Portland, Acadia NP, White Mountains, Green Mountains, The Berkshires, Mystic, Newport and Cape Cod.

For the full loop, we recommend allowing 3 weeks or more. But you can break the itinerary up and enjoy a shorter journey, too, for example, focusing on the coast or the mountains.

With 7 days, it’s as good idea to concentrate on a certain area. To see both a lively city and New England’s timeless coastal environment, a popular combo is Boston and Cape Cod.

Keep planning your New England trip

• Scan the best things to do in New England
• Book beautiful Cape Cod accommodation
• See the best lodging near Acadia NP

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The Flexible New England Road Trip Itinerary You Need in 2024 ❤️

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Are you planning the ultimate New England road trip? Let me help! After exploring New England for more than 20 years, I have put together this comprehensive guide to exploring this charming region. The best way to see New England is by car, and this 2-3 week itinerary offers a grand tour of New England, covering the best places to visit , especially for first-time visitors.

Spanning Connecticut, Massachusetts, Maine, Vermont, New Hampshire, and Rhode Island, this itinerary shows you the best of New England, from quaint coastal towns to lush mountain landscapes. The itinerary is also well-paced to allow you to spend time seeing the sites, enjoy local activities, and cross items off your New England bucket list . And, the itinerary is flexible and can be adapted to your needs, interests, and desired trip length.

Whether you’re in for the full journey or seeking shorter road trip variations (I’ve included those, too!), this guide caters to your wanderlust, ensuring a memorable and personalized exploration of New England’s beauty. Let’s go!

PS: Pop this New England playlist on—it’s perfect for a road trip!

Table of Contents

New England Road Trip FAQ

When’s the best time of year to road trip new england.

New England is gorgeous in all seasons, but for the easiest driving (and best New England road tripping experiences), summer and fall are ideal.

If you want the fall foliage experience, late September and early October are the key weeks to plan for. Of course, these times of years are also peak tourist season, so expect more traffic and higher hotel prices.

(PS: If you want to do a shorter road trip or a route that’s perfect for fall, check out my 7 day New England Fall Road Trip itinerary!

One of my favorite times of the year in New England is mid to late May. The weather is beautiful, and the region’s roads and attractions are generally less busy. The budding greenery is especially gorgeous and fresh, too.

Early September can also be lovely, just after kids have returned to school and summer has ended. Expect crisp temperatures and leaves just beginning to change colors.

A winter road trip may be doable, but remember, New England can be quite snowy, so you’ll want to have a reliable vehicle outfitted with snow tires, and you’ll need to stay aware of changing weather conditions and road closures.

How many days do you need for a road trip to New England?

You need 2-3 weeks for a comprehensive road trip around New England. This is the ideal amount of time needed to cover the major highlights of all six New England states.

If you don’t have that much time, you can still pack a lot into a shorter trip. A minimum of 7 to 10 days is ideal for a thorough yet relaxed New England road trip. For a 7-10 day trip, consider my Southern or Northern New England itineraries, or do shorter segments of the full 2-3 week itinerary.

Where should I start my road trip through New England?

I’ve started this New England travel itinerary in Boston, as it’s the biggest city in New England and home to a major airport, Boston Logan International. This airport is easy to fly into and rent a vehicle. Boston is also a great destination on its own, so my itinerary includes a couple days exploring the city.

Ps: Ready to rent a car for your New England drive? Click here to find the best rates on rental cars !

The Perfect New England Road Trip Itinerary

Days 1 & 2: boston, massachusetts.

You’ll start your New England excursion from Boston, Massachusetts: an absolutely fantastic city.

Boston is a well-known place that’s filled to the brim with history. From famous historical events like the Boston Tea Party to its reputation as a modern-day sports town, you’ll never be bored here.

Some great things to do in Boston :

• Visit the North End and dine on amazing Italian food . Don’t miss grabbing cannoli from Mike’s Pastry and Modern Pastry.
• Stroll around quaint Beacon Hill
• Tempt your taste buds with a Boston Food Tour
• Go shopping on classy Newbury Street
• Follow the Freedom Trail to learn Boston’s revolutionary history
• Join an expert-led walking tour for a more in-depth experience of the city
• Check out one of the many great Boston museums, including the Museum of Science which I especially love
• Join a Boston Duck Tour and ride in one of the famous amphibious vehicles

Hotel Suggestion in Boston: Fairmont Copley Plaza

Need more guidance for Boston? Check out my post on The Top Things to Do in Boston for first timers , and I’ve also got some recommendations on where to grab coffee, breakfast , a beer, or a bite to eat in Boston , too !

PS: Looking for a shorter road trip from Boston? Check out my New England trip itinerary focusing on the journey from Boston to Acadia National Park .

Days 3 & 4: Newport, Rhode Island

On Day 3, drive from Boston to Newport. This is a straightforward route, with about 2 hours of drive time. Glitz and glamour. That’s what you’ll find in Newport, Rhode Island. This town is perhaps best known for its iconic Gilded Age mansions . These opulent buildings were once the summer cottages of America’s rich and famous families.

Today, many of them have been converted into museums that you can wander through and admire some of New England’s opulence past.

Some of my favorite things to do in Newport:

• Visit a mansion or two. I recommend The Breakers if you only have time for one of Newport’s mansions
• Hop on this fun Gilded Age Mansions Tour, which takes you around via trolley
• Stroll along the scenic Cliff Walk
• Dine at the White Horse Tavern, America’s oldest operating restaurant

Hotel Suggestion in Newport: Hotel Viking

For further Newport ideas : Click here to read more about the top things to do in Newport, including beaches, restaurants, hotels , and vacation rentals too!

READ NEXT   15 Festive Things to Do for Christmas in Newport RI

Day 5: Mystic, Connecticut

Mystic, Connecticut is a wonderful little seaside town that feels like a must-do on a New England adventure. It is one of my favorite places in New England, and there is plenty to do here: history, culture, art, sailing. And, for seafood lovers, Mystic’s coastal location offers a variety of delicious seafood dining options

Like pretty much every other scenic New England town, there’s a cute little downtown area with great shopping, dining, and activities.

A few terrific things to do in Mystic:

• Explore Mystic Seaport , a historic shipyard and museum destination you could spend hours touring
• Watch the Mystic drawbridge (the Mystic River Bascule Bridge) go up, especially while enjoying some Mystic Drawbridge Ice Cream !
• See the adorable beluga whales at Mystic Aquarium
• Browse the epic shops in Olde Mystick Village including my personal favorite: Alice’s Haunted Little Bookshop

Hotel recommendation for Mystic: The Whaler’s Inn

Further reading on Mystic: Check out my tips for all the fun things to do , best restaurants to eat at , and the best places to stay in Mystic!

READ NEXT   25 Best Beach Towns in New England for Coastal Fun

Day 6: Litchfield Hills, Connecticut

As you roadtrip New England, your next destination is the enchanting Litchfield Hills . This is another easy drive day, as the distance from Mystic to the Litchfield region is a short 2 hours. And if you’re traveling in the fall, the Connecticut fall foliage along this route creates a magical backdrop. To me, this area in the northwest corner of the state is a hidden gem .

Here you’ll find all the classic New England pastimes you know and love. In particular, there is an abundance of outdoor activities (hiking, paddling, fishing) as well as exceptional antique shops.

The Litchfield Hills make up a large portion of this region, and include towns such as Torrington, Woodbury, Kent, Cornwall, and Washington (very English sounding names, aren’t they?)

A few excellent things to do in the Litchfield Hills:

• Live out your Gilmore Girls Dreams. This region is well known for being the inspiration for the iconic tv show that perfectly encapsulates New England small town charm .
• Grab ice cream from Arethusa Farm
• Go covered bridge chasing – Bulls Bridge in Kent has a worthwhile nearby hiking trail
• Hike to Campbell Falls, a beautiful waterfall (this trail technically takes you over the border into Massachusetts, too, so it’s a 2-for-1!)

Recommended hotel in the Litchfield Hills: The Mayflower Inn & Spa : legend has it that it was the inspiration for Lorelei Gilmore’s inn, the Dragonfly.

READ NEXT   18 Wonderful Weekend Getaways from Boston

Day 7: Lenox, Massachusetts

Continue on your New England road trip into the Berkshires of Massachusetts . Here you will encounter art, nature, and culture combined. This region has been very popular among vacationers for many years.  And the town of Lenox is the center of it all.

Best things to do in Lenox:

• Enjoy a concert at the famous Tanglewood (these are a staple in summer, and you can hear everything from leading symphonies to folk singers like James Taylor
• Take in a performance at Shakespeare & Company. This theatre produces excellent shows; I’ve been twice!
• Take a hike on one of the area’s many scenic trails
• Step back in time at the Ventfort Hall Mansion and Gilded Age Museum, a 1890s home that’s open for tours.
• If you are interested in literature, you may also wish to stop by the Mount, Edith Wharton’s turn-of-the-century estate.

Where to stay in Lenox:

More resources for your trip to Lenox and the Berkshires: 🍁 Best Restaurants in Lenox 🍁 10 Charming Cabins in the Berkshires 🍁 Best Hikes in the Berkshires

Day 8: Manchester, Vermont

Finally, you’ve made it into the spectacular state of Vermont (my personal favorite, if you couldn’t tell). It’s a fairly easy drive from the Berkshires in Massachusetts up to Manchester in the southwestern corner of Vermont, only a couple of hours. And this is another route that is especially glorious if you opt to do a New England fall road trip .

Manchester is one of the most beautiful places in Vermont, marrying quaint village charm with touches of modern luxury. It’s no surprise that it’s very popular among travelers.

Some of my favorite things to do in Manchester:

• Tour Hildene , the beautiful Lincoln family home (Yes, some of Abraham Lincoln’s children lived here!)
• Drive to the top of Mt. Equinox on Skyline Drive (or consider hiking the trail up to the summit)
• In the fall, pick pumpkins from the patch at Equinox Valley Nursery (and don’t miss the cider donuts!)
• Shop til you drop at Manchester’s many outlet stores
• Dine at the stately Ye Olde Tavern
• Pop into Northshire Bookstore , one of the leading independent bookstores in New England

Hotel Recommendation for Manchester: Kimpton Taconic Hotel

More resources on Manchester: Read my entire Manchester VT travel guide for more of the top Manchester activities, as well as these articles on the best restaurants , breakfast spots , and hotels in Manchester .

READ NEXT   25 Best Hikes in New England: New England Hiking Options for Everyone

PS: If you’re very interested in exploring Vermont, a trip through Manchester, Burlington, and Stowe make the ideal Vermont road trip itinerary .

Day 9: Burlington, Vermont

Just around 2 hours north of Manchester (taking the beautiful and scenic Route 7) you’ll find yourself in Burlington: Vermont’s biggest city. It’s also often mislabeled as Vermont’s capital, but that honor goes to Montpelier. Still, you’re likely to run into Bernie Sanders in either town!

Burlington is where my husband and I lived for several years. It’s a fantastic town that is hip, artsy, and full of good, local food . Seriously, in Vermont, you need to eat. There’s so much delicious cheese, coffee, beer, maple syrup, and much, much more.

To get you started on your culinary adventures, check out this post on my favorite Burlington breweries and bars , and this one on my beloved coffee shops. Oh, and don’t forget to enjoy brunch in BTV . We do breakfast here right.

The gem of Burlington is Lake Champlain, the sprawling, sparkling lake that the city overlooks. Here is the chance to go sailing, stand-up paddleboarding, or take a ferry across to New York state.

If you’d prefer to stay on dry land, visit one of the many beautiful parks and natural areas. Burlington is amazing for outdoor activities. If you want to get moving, the Burlington Bike Path stretches for miles, hugging the lake’s edge. This is ideal for running or cycling. You can even rent bikes right on the bike path.

More epic things to do in Burlington VT:

• Sail on Lake Champlain on the Spirit of Ethan Allen cruise
• Walk down Church Street for shopping, eats, people-watching, and more
• Hike Mt. Philo, a nearby easy hike with the payoff of a fantastic view

Hotel recommendation in Burlington: Hotel Vermont

Even more resources for your Burlington trip:  🍁 21 Hikes Near Burlington VT to Add to Your Bucket List  🍁 10 Can’t-Miss Free Things to do in Burlington VT  🍁 9 Incredible Day Trips from Burlington VT 🍁 Where to Stay in Burlington VT in 2023: Best Burlington Hotels

PS: Considering visiting Burlington in 2024? It’s one of the cities that the total solar eclipse will pass fully over on April 8, 2024, so start planning ASAP!

Days 10 & 11: Stowe, Vermont

From Burlington, head south on I89 to Exit 10. From there, you’ll take the scenic Route 100 past Waterbury and out to Stowe. When people think of the classic Vermont places, they’re likely thinking of Stowe.

It’s absolutely gorgeous: a charming town surrounded by mountains. The short Main Street and its side streets boast a white-steepled church, an old-timey general store, and a ski museum.

Simply put, Stowe is adorable. I have been to Stowe countless times and I highly recommend it as one of the premier New England road trip destinations!

Wonderful things to do in Stowe:

• Traverse the trails and property at the Trapp Family Lodge , and grab a beer afterwards at their European-style brewery and Bierhall
• Shop the adorable shops on Main Street
• Visit a haunted covered bridge if you dare (Emily’s Bridge)
• Spend a day skiing on one of the area’s fantastic ski mountains
• One of my number one tips: on your way to Stowe, stop by Cold Hollow Cider Mill for all things apple (a must-visit in the fall) and the Ben & Jerry’s Ice Cream Factory tour .

Where to stay in Stowe: Field Guide Lodge , Topnotch Resort , or the Trapp Family Lodge

More on Stowe: I have an entire post dedicated to Things to Do in Stowe, Vermont, the best restaurants , the best breakfast , the best hikes , the best hotels , everything!

READ NEXT   15 Gorgeous VRBO & Airbnb Stowe VT Vacation Rentals (2023)

READ NEXT   Stowe Vermont in Summer: 11 Fun Things to do for All Ages

Days 12 & 13: The White Mountains, New Hampshire

No adventure in New England could be complete without some mountain time. And this is especially true if you’re planning a New England fall road trip .

New Hampshire’s White Mountains are impressive and exciting. They’re the tallest in New England (with Mount Washington tallest of all) and offer spectacular hiking and more. There are several places you could base yourself during this portion of the road trip, but I recommend North Conway, Lincoln, or North Woodstock, as they each offer lots of amenities and accommodations, and are a reasonable distance from the most popular attractions in the region.

Unmissable things to do in the White Mountains:

• Take in some of the coolest natural wonders of the White Mountains , such as the Basin, a granite “pothole” that is found at the base of a waterfall in Franconia Notch State Park
• Go hiking! This is the #1 item on any New Hampshire bucket list . And here is a guide to some of the best hikes in New Hampshire .
• Meander through Flume Gorge. This is a natural ravine that formed over many years and now a hiking trail with a boardwalk passes through it. This is a wonderful hike with some amazing scenery. Another spot that is extra special with the fall foliage
• Clark’s Trading Post in Lincoln, an old-fashioned New Hampshire classic
• A scenic drive along The Kancamangus Highway. This epic stretch of road runs 26 miles between Lincoln and Conway and is one of New Hampshire’s most scenic roads . There are many great spots to stop and explore further and this is undoubtedly one of the best places to see New England fall foliage.
• Shop in North Conway, and don’t miss Zeb’s General Store for a taste of pure nostalgia.
• Tube or paddle in the Saco River. On a friend’s recent bachelorette party trip, we used Saco River Tubing and had an absolute blast!
• Near Bartlett you can stop by Diana’s Baths, a beautiful area of cascading waterfalls and gentle pools. On a hot summer’s day, it’s the perfect place to cool off.

Where to Stay in the White Mountains: Lumen Nature Retreat

More White Mountains travel guides:  🍁  Best Things to Do in North Conway, NH  🍁  Best Things to Do in Lincoln, NH  🍁  Best Things to Do in Franconia, NH  🍁  15 Amazing Cabins in the White Mountains, NH

READ NEXT   Your Guide to Mt Washington NH: The Highest Peak in the Northeast!

Days 14 & 15: Portland, Maine

Finally, the last state on the great New England road trip. This is Maine, “the way life should be.”

Maine is massive so there’s no way to do the state justice in this itinerary; I’m essentially covering a few of the must-see areas. You could spend weeks on a road trip of Maine alone. (See also these  8 autumn scenic drives in Maine delivering up insane fall colors).

If you do wish to explore the rest of Maine (and you absolutely should) I recommend taking a look at my epic list of 50+ Fun Things to Do in Maine , as well as this guide to the top places to visit in Maine . But let’s continue with our amazing road trip!

Stop for a bit in Portland, a modern portside town that may surprise you. There’s a hip city right on the water in Portland, Maine, and this is a hot spot for restaurants, coffee shops, breweries, bakeries , and entertainment .

Fun things to do in Portland:

• Visit a brewery. Beer lovers will be happy to know that Portland has 18 breweries all its own .
• Check out one of several lighthouses in the area . There are 5 less than 20 minutes’ drive from Portland, including the iconic Portland Head Light.
• Grab some of that famous Maine lobster.
• Stuff your face with Maine potato donuts from local staple The Holy Donut
• Walk the pretty Old Port and patronize the eclectic shops and restaurants
• Don’t miss dining at Hot Suppa , a West End restaurant where I enjoyed the best breakfast of my life (and a spectacular maple latte)
• Traveling with kids? The Children’s Museum of Maine on Thompson’s Point is a total blast!

Portland hotel recommendation : Hotel Francis in the West End

Further resources for discovering Portland:  🍁 The Best Things to Do in Portland, Maine  🍁 Weekend in Portland Itinerary  🍁 7 Spots for the Best Breakfast in Portland Maine  🍁 14 Exceptional Airbnb Portland Maine Rentals 🍁 12 Best Hotels in Portland Maine

Days 16 & 17: Acadia National Park and Bar Harbor, Maine

Now we travel north to Bar Harbor. Admittedly, it looks like a far drive on the map. In reality, from Portland to Bar Harbor is just over a 3-hour drive. And trust me, visiting Mt. Desert Island is SO worth it.

Bar Harbor is the seaside town that will be your base for exploring Acadia National Park . You will be in awe over this beautiful part of Maine. Here is where rocky cliffs tumble into the sea, with iconic lighthouses at the top.

There’s abundant wildlife on land and in the sea, and countless opportunities for terrific hiking.

But the region is not just about the outdoors. Bar Harbor has lovely shops, restaurants, and extremely cozy inns . Truly, the region is ideal for travelers of all kinds. You’ll also find great camping, cabins , and vacation rentals in and near Acadia, too.

My top recommendations in Acadia National Park and Bar Harbor:

• Tackle the exhilarating Beehive Hike, that involves a bit of climbing and rewards you with unparalleled views
• Order popovers at the Jordan Pond House (delicious!)
• Take a whale watch or other wildlife tour from Bar Harbor
• Drive up Cadillac Mountain before dawn to catch the sunrise from the first place light touches in the Continental US
• Marvel at the natural wonder of Thunder Hole
• Bike the Carriage Roads in Acadia National Park

Bar Harbor hotel recommendation: The Bar Harbor Inn

More on Acadia: Check out my 3 Day Bar Harbor and Acadia National Park Itinerary for an awesome trip!

Read Next :  10 Coastal Towns in Maine That are Hidden Gems

Day 18: Portsmouth, New Hampshire

Your New England driving tour itinerary is nearing its end, but you’ve got a few more stops to make—-stops you won’t want to miss.

Portsmouth is first. We’re back in New Hampshire now! Between Maine and Massachusetts, New Hampshire is home to a very small strip of coastline. The hub of the Seacoast is Portsmouth, a small yet lively city with a great deal of history. You can see colonial architecture all over this beautiful city.

Taking a New England winter road trip? Portsmouth should definitely be on your list, as they do a month of celebrations and events with Vintage Christmas, one of the most magical New England Christmas celebrations !

Best things to do in Portsmouth:

• Strawbery Banke Museum: an outdoor living history museum.
• Dine at one of the many awesome restaurants: Portsmouth has become a major foodie destination in recent years
• Go shopping at the numerous boutiques around town. Some standouts: Gus & Ruby Letterpress , Pickwick’s Mercantile , and G. Williker’s Toy Shop
• Be surrounded by books and grab a tasty beverage at Book & Bar
• Wander the lovely Prescott Park
• Attend some award-winning theatre at Seacoast Repertory Theatre

Hotel suggestion in Portsmouth: The Hotel Portsmouth

Further Portsmouth NH travel resources for your trip : 🍁 The Best Things to Do in Portsmouth, NH 🍁 Top 10 Bars in Portsmouth NH

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Day 19: Salem, Massachusetts

Your final stop is the historically infamous Salem, Massachusetts. And though you’ll definitely want to spend time exploring its history with the Salem Witch Trials, there’s plenty to do in the area that isn’t witchy, too.

You can hit the highlights of Salem in one day, or extend for another 2-3.

If possible, you don’t necessarily want to plan your trip to Salem to coincide with Halloween. Although the town has a distinct, fun vibe this time of year, October is also its busiest and most crowded month.

No matter when you go, however, there are definitely some things not to be missed:

• Go to The Witch House, an atmospheric home you’ve definitely seen on Instagram, and a building that is one of the only Salem locations with direct ties to the witch trials. (One of the judges lived here).
• Get witchy in the magickal shops. Whether you want something more fun and touristy, or you’re after the real deal, Salem has a wide range of shops selling all kinds of goods.
• Tour the House of the Seven Gables
• Walk the neighborhoods around Federal Street and admire the stately historic homes
• Find the Hocus Pocus film locations! (Use my guide to take a DIY Hocus Pocus tour )
• Get spooked on a nighttime ghost tour ( top recommendations here !)
• Grab a photo with Samantha at the Bewitched Statue

Hotel recommendation for Salem : The Hawthorne Hotel or Hotel Salem (they have a great rooftop bar)

More on Salem: Check out its great restaurants , scope out some of its haunted history , and maybe even stay overnight in one of Salem’s classic New England inns or Airbnbs ! Nearby towns of Rockport, Gloucester , and Marblehead are worth visiting too if you’d like to explore more of this area of coastal New England.

READ NEXT   12 Fun and FREE Things to Do in Salem MA

Day 20 / End: – Boston, Massachusetts

You did it! You’ve completed an epic New England road trip! Congratulations! You’ve seen some of the prettiest places in the country, and you did it all by car!

Days 21+: Optional Add-Ons: Cape Cod/Nantucket/Martha’s Vineyard

You may be wondering why I didn’t include some of New England’s coastal gems on this New England road trip itinerary? I did this because destinations such as Cape Cod , Nantucket, and Martha’s Vineyard are harder to get to and don’t fit in well with the traditional road trip format. After all, Nantucket and Martha’s Vineyard are islands, so they are not an easy destination to access without in-depth planning.

Not only are they more complicated to travel to, these Massachusetts coastal destinations are terrific and truly worthy of their own vacations . I highly recommend devoting a trip specifically to exploring New England’s amazing coast.

If you wish to add to your road trip, by all means, hop in the car and continue the drive to Cape Cod. From there you can easily take a day trip to Martha’s Vineyard or Nantucket. And I hope these resources will help you as you plan:

More travel ideas here:

• 25 Things to Do on Cape Cod (Besides the Beach!)
• 13 Best Hotels on Cape Cod: Where to Stay on the Cape
• 10 Best Hotels on Nantucket: Where to Stay for a Nantucket Getaway
• 25+ Fun Things to Do in Martha’s Vineyard

The Ultimate New England Road Trip Map (2-3 weeks)

The map below includes all of the destinations I’ve outlined above.

In need of some extra New England road trip ideas? If you’re limited on time, check out my Northern and Southern New England road trip itineraries. These are ideal for 5 day, 7 day, or 10 day New England road trips. Your own personal planning maps are below!

Northern New England Road Trip 7-10 Day Itinerary

• Woodstock, VT
• Waitsfield, VT
• Lincoln, NH
• Portland, ME

Here’s a great New England road trip route if you just don’t have time to go everywhere, but you want to see the highlights of northern New England. In any trip you’ll have to make some choices about what to see and what to miss, sadly, but with this road trip itinerary, you’ll definitely have a broad experience of Northern New England.

This one week New England itinerary contains many of the same stops you’ll find on the ultimate version (that covers all six states). But this one also has the addition of Woodstock, Vermont, which is a classic New England spot, really a ‘Currier and Ives town.’

Southern New England Road Trip 7-10 Day Itinerary

• Provincetown, MA
• Newport, RI
• Providence, RI
• Stonington, CT
• Litchfield Hills, CT
• Gloucester, MA

The Southern New England road trip route is ideal for those who really seek a coastal trip, or who aren’t quite as interested in exploring the mountains. This trip adds a whole bunch of extra stops so you can really dive into coastal New England.

It gives you a feel for the more outdoorsy areas of these southern New England states, too, as the itinerary brings you through the Berkshires, and through charming parts of Connecticut. Definitely an option for a lovely New England summer road trip itinerary.

Shorter Scenic Drives in New England

Are you just looking for a short scenic route that allows you to see dramatic coastal cliffs, mountainscapes, scenic countryside, and more of New England’s charm?

Whether you’re looking for fall scenic drives in New England, beautiful routes along the coast, or just a short yet pretty New England drive, you might just find what you’re looking for on this list of short, scenic drives in New England.

Scenic Drives in New Hampshire

The Coastal Byway (Route 1A)

Location: Portsmouth to Seabrook 

Distance: 18.5 miles 

Where to Stop:  

• Hampton Beach
• Surf Portsmouth , Portsmouth 
• Strawbery Banke Museum , Portsmouth

Robert Frost Scenic Byway

Location: Southern New Hampshire

Distance: 43 miles (The Old Stagecoach Byway and the Robert Frost Byway combined) 

Where to Stop: 

• Robert Frost Farm State Park , Derry 
• Civil War Memorial, Chester
• Matthew Thornton House, Derry 
• Town Beach, Hampstead

New Hampshire Route 112 (Kancamagus Highway)

Location: Conway to Bath

Distance: 56.39 miles 

• Sabbaday Falls 
• Albany Covered Bridge 
• Swift River Lower Falls  
• Russell-Colbath House 
• Sugar Hill Scenic Overlook

The Lake Winnipesaukee Loop

Location: The Lakes Region 

Distance: 97 miles

• George’s Diner , Meredith 
• Mt. Major Trail, Alton 
• Dewey’s Ice Cream Parlor and Cafe , Center Harbor 
• Cotton Valley Rail Trail , Wolfeboro 
• Abenakee Tower , Tuftonboro

Scenic Drives in Maine

• Moosehead Lake

Location: Kennebec and Moose River Valley

Distance: 59 miles

Where to Stop:

• Lily Bay State Park
• B52 Crash Site
• Mount Kineo
• Stress Free Moose Pub & Cafe

U.S. Coastal Route 1 

Location: Kennebunkport to Bar Harbor

Distance: 200 miles

• Goose Rocks Beach , Kennebunkport
• Portland Head Light , Cape Elizabeth
• Old Orchard Beach Boardwalk, Old Orchard Beach
• The Holy Donut, Portland
• Farnsworth Art Museum, Rockland
• Jordan’s Restaurant , Bar Harbor

Acadia All American Road from Trenton to Acadia

Location: Trenton to Bar Harbor

Distance: 40 miles

• Thunder Hole
• Bar Harbor Inn & Spa

Scenic Drives in Vermont

Location: Wilmington to Jay 

Distance: 184 miles

• Molly Stark State Park, Wilmington
• Dot’s Restaurant , Wilmington
• The Vermont Country Store ,  Weston
• Green Mountain Sugar House ,  Ludlow
• Moss Glen Falls, Granville
• Ben & Jerry’s Factory , Waterbury
• Cold Hollow Cider Mill ,  Waterbury Center
• Trapp Family Lodge ,  Stowe

Route 9 – The Molly Stark Byway

Location: Brattleboro to Bennington 

Distance: 40.1 miles

• Vermont Country Deli , Brattleboro
• Creamery Bridge, Brattleboro
• Southern Vermont Natural History Museum, West Marlboro
• Hogback Mountain Scenic Lookout, Wilmington
• Bennington Battle Monument, Bennington
• The Apple Barn and Country Bakeshop – Bennington

Location: Bennington to Burlington 

Distance: 122 miles

• The Bennington Battle Monument, Bennington
• The Robert Frost Stone House Museum , Shaftsbury
• Cider donuts at the Equinox Valley Nursery , Manchester
• Downtown Murals, Rutland
• Woodchuck Cider , Middlebury
• The Burlington Waterfront – Burlington
• Church Street/Downtown – Burlington

Rhode Island Scenic Drives

Ocean drive.

Location: Fort Adams Park to Bellevue Ave

Distance: 10 Miles

• Castle Hill Lighthouse
• Brenton Point State Park
• Fort Adams Park
• The Breakers
• Marble House
• Rough Point
• The Red Parrot Restaurant

Scenic Drives in Connecticut

Connecticut state route 169.

Location: Norwich to Woodstock

Distance: 36 miles

• Lisbon Meadows Park, Lisbon
• Prudence Crandall Museum , Waterbury
• New England Center of Contemporary Art, Brooklyn
• Roseland Cottage , Woodstock

Connecticut Shoreline Drive

Location: New Haven to Stonington Borough

Distance: about 80 miles (depending on which routes you take!)

• Eat in Little Italy, New Haven
• Hammonasset Beach State Park, Madison
• Harvey’s Beach, Old Saybrook
• Rocky Neck State Park, East Lyme
• Mystic Aquarium, Mystic

Scenic Drives in Massachusetts

The berkshires.

Location: Stockbridge to Williamstown

Distance: 35 miles

• Norman Rockwell Museum , Stockbridge
• Berkshire Botanical Garden,  Stockbridge
• The Mount, Edith Wharton House , Lenox
• Berkshire Museum, Pittsfield
• Hancock Shaker Village, Hancock
• Mount Greylock , North Adams
• Massachusetts Museum of Contemporary Art , North Adams
• Williams College – Williamstown

Essex Coastal Scenic Byway

Location: Gloucester to Newburyport 

Distance: 24 miles

• Hammond Castle Museum, Gloucester
• Crane Wildlife Refuge, Essex
• Eat at the Clam Box , Ipswich MA
• Plum Island Beach, Newburyport
• Maudslay State Park, Newburyport

Wrapping Up this Northeast Road Trip

I hope this New England travel guide has given you all the information you need to help you plan a trip to the region’s most exciting and gorgeous places. With multi-day options to choose from and choices that are great for every season, I have aimed to cover all of the top places to road trip throughout these six amazing states.

Even more resources for your New England adventures: 🍁 25 Fantastic New England Day Trips 🍁 Hidden Gems in New England: 15 Secret Places to Visit 🍁 Best Fall Foliage New England Tours Worth Your Money

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The Ultimate New England Road Trip Itinerary

Get acquainted with the birthplace of America on a New England road trip. Discover the quaint coastal towns, famous historical landmarks, and spectacular scenic drives the area has to offer. Our trip includes additional states, but the bulk of our itinerary is in six states: Connecticut, Rhode Island, Massachusetts, New Hampshire, Maine, and Vermont.

It’s for 60 days, starting and ending in Chicago and driving roughly 2,500 miles, but you can adjust it to your liking. Visit one national park, too-many-to-count lighthouses, a few state parks, picturesque small towns, and overindulging on copious amounts of seafood along the way.

If you are looking for more unforgettable adventures, check out these trips: Chicago to L.A. via Route 66 , hiking 500 miles on the Camino in Spain , and a cross country road trip to thirteen national parks.  

When to Visit New England

From our experience and research, there really is no bad time to visit New England. Each season brings something unique to the table.

Winter is cold and snowy but perfect for winter activities such as skiing and snowboarding. The thawing temperatures of spring bring wildflowers and maple syrup. Summer is known for its hot weather and sunny days filled with outdoor adventures. And last but not least, fall welcomes a blanket of blazing colored treetops and great hiking temperatures.

WAIT UNTIL YOU READ WHAT WE HAVE PLANNED! SCROLL DOWN FOR MORE INFO

One of the Top Spots for Fall Foliage in the U.S.

So why did we choose New England this trip? We have had an east coast road trip on our radar for quite some time and especially wanted to visit during the fall. It is touted as one of the best locations for fall foliage in the United States.

Donned in our heavy sweaters as autumn unfolds with rich colors of crimson and gold with the smell of fire and a hint of pumpkin spice floating in the air, I can’t imagine a better time.

Hopefully, from mid-September until the end of October, we will be leaf peeping fools.

Ultimate New England Road Trip Itinerary Summary

Keep Scrolling for our detailed New England Self Drive Itinerary.

Summary starting and Ending in Chicago, Illinois

• Put-in-Bay, Ohio (2 nights)
• Erie, Pennsylvania (1 night)
• Watkins Glen State Park, New York (3 nights)
• Litchfield, Connecticut (1 night)
• Hartford, Connecticut (2 nights)
• New Haven, Connecticut (1 night)
• Niantic, Connecticut (1 night)
• Mystic, Connecticut (2 nights)
• Block Island, Rhode Island (1 night)
• Portsmouth, Rhode Island (2 nights)
• Providence, Rhode Island (2 nights)
• Provincetown, Massachusetts (1 night)
• Falmouth, Massachusetts (1 night)
• Martha’s Vineyard, Massachusetts (3 nights)
• Plymouth, Massachusetts (1 night)
• Salem, Massachusetts (1 night)
• Hampton Falls, New Hampshire (1 night)
• Kennebunkport, Maine (1 night)
• Acadia National Park / Bar Harbor (8 nights)
• Bangor, Maine (2 nights)
• Baxter State Park, Maine (3 nights)
• Lily State Park, Maine (2 nights)
• White Mountains, New Hampshire (6 nights)
• Burlington, Vermont (2 nights)
• Stowe, Vermont (2 nights)
• West Dover, Vermont (7 nights)
• Buffalo, New York (1 night)
• Chicago, Illinois

Day 1: Chicago, Illinois to Put-In-Bay, Ohio

We leave Lake Michigan to head over to Lake Erie, the southernmost lake of the Great Lakes. It is also the shallowest which makes its water temps the warmest.

Our first stop is Put-In-Bay, a small village on South Bass Island. Known for its party-hearty culture, we are determined to not only imbibe a bit but also to discover the hidden gems on the island.

Driving Info: 279 miles, 5 hrs 20 minutes with a ferry ride

READ NEXT: TOP 10 THINGS TO DO IN PUT-IN-BAY

Day 2: Put-In-Bay, Ohio to Erie, Pennsylvania

We were beckoned to drive along the Lake Erie coast when we visited Cleveland a few years ago but didn’t include the ride on that trip. Up the waterline, we go, as we leave Put-In-Bay to explore the small towns and lighthouses along the way.

Who knew Pennsylvania has a sliver of land right on the lake? We stop for the night at Presque Isle State Park, a small park on a sandy peninsula that juts into Lake Erie. If you are interested in renting an RV and starting in Pennsylvania, check out RV Rental Philadelphia, the largest, most trusted RV Rental marketplace with a wide-ranging inventory.

Driving Info: 190 miles, 3 hrs 45 minutes with a ferry ride

RELATED: COOL STOPS ALONG OHIO’S LAKE ERIE COASTAL TRAIL

Days 4 – 6: Erie, Pennsylvania to the Finger Lakes, New York

The Finger Lakes region in New York is known for a series of pristine lakes and beautiful vineyards. The area is also home to a number of hiking trails, breweries, distilleries, and hard-cider producers.

Driving Info: 198 miles, 3 hrs 15 minutes

READ MORE: 3 DAY FINGER LAKES ITINERARY

Day 7: Finger Lakes to Litchfield Hills, Connecticut

Ever heard of the television show, Gilmore Girls ? Today, we reach our first New England state, Connecticut, where the fictional town of Stars Hollow was based on. We are touring the northwest hills in search of magical towns like Washington, New Milford, Bantam, and Litchfield which inspired the creators of the show.

Driving Info: 297 miles, 5 hrs

RELATED: A CONNECTICUT BUCKET LIST FOR YOUR NEXT TRIP

Days 8 & 9: Litchfield Hills to Hartford, Connecticut

And we are off to the state capital of Hartford, one of the oldest cities in the United States. Founded in 1635, we are bound to find some historical places to visit. A few on the list so far are Trinity College, Wadsworth Art Museum, and Bushnell Park.

The one I’m most excited about is the Mark Twain House where he wrote some of his most famous works and raised his family.

Driving Info: 32 miles, 50 minutes

Day 10: Hartford to New Haven, Connecticut

Let’s make our way to the water again, New Haven is situated along the Long Island Sound in southern Connecticut. It’s the first planned city in America and home to Yale, one of the oldest universities in America.

Oh and apparently, home to some of the best pizza in the country. This Chicago-born Midwesterner writes with a probably-not-side-grin. But hey, you never know!

Driving Info: 39 miles, 40 minutes

Day 11: New Haven to Niantic, Connecticut

On our way to Mystic, we plan to take a leisurely drive along the coast to dip in any beach towns with a view. At lunch, we will find our first lobster roll of the trip. The word on the street is that Connecticut’s rolls are not made with mayo, just butter and a squeeze of lemon so it’s a must-try.

Driving Info: 42 miles, 45 minutes

Days 12 & 13: Niantic to Mystic, Connecticut

Never did I imagine a New England road trip would have me hunting down pizza, but stopping at Mystic Pizza is a MUST in my eyes. My love for Julia Roberts isn’t the only reason we are stopping here, the seaside village is brimming with charm and boasts the nation’s largest maritime museum.

Driving Info: 18 miles, 25 minutes

Day 14: Mystic to Block Island, Rhode Island

With a declaration from the Nature Conservancy that Block Island is one of its “Last Great Places,” it was a given that we were going to zip our way over once we cross into Rhode Island. As if dramatic rugged bluffs weren’t enough to put us over the edge (literally and figurately), the 365 freshwater ponds and rolling green hills had us hooked.

Driving Info: 54 miles, 2 hrs 15 minutes with a ferry ride

Plan Your Trip Here: Amazing Things to Do on Block Island

Days 15 & 16: Block Island to Portsmouth, Rhode Island

Portsmouth is our base location for exploring the grandeur Newport Mansions of the social elite like the Vanderbilts and Astors. Ah, the Gilded Age, when the rich were rich and wanted everyone to know it.

After a few tours such as the Biltmore Estate and  Stan Hywet Hall and Gardens, we’ve become obsessed with these over-the-top homes. We can’t wait to stroll the Cliff Walk, a 3.5 mile National Recreation Trail that hugs the Newport shoreline offering gorgeous coastline and mansion views.

Driving Info: 46 miles, 2 hrs 11 minutes with a ferry ride

How to Choose the Best Newport Mansion Tour

Days 17 & 18: Portsmouth to Providence, Rhode Island

Cheers to hitting another state capital! Providence is the cultural hotspot of New England. With a vintage feel in a college town and the most coffee and doughnut shops per capita of any city in the country, I’m sure we’ll keep busy, or at least our mouths will.

Driving Info: 29 miles, 32 minutes

Day 19: Providence, Rhode Island to Provincetown, Massachusetts

Onward to the Cape! Cape Cod that is. And it is here where we will have one of the most anticipated experiences of the trip, a whale watching tour!

Situated at the tip of Cape Cod, Provincetown is a quirky artsy area that also happens to be a jumping point for whale watching tours.

Driving Info: 120 miles, 2 hrs 12 minutes

Day 20: Provincetown to Falmouth, Massachusetts

Today is a day for moseying around the island stopping at captivating waterfront villages and maybe a local food shack or brewery. Since we brought our bikes, we will roll onto the Shining Sea Bikeway, a 10.7-mile path that runs from the coast in Falmouth to Woods Hole and then past to North Falmouth. 

Overnight is at Falmouth so we can get an early ferry over to Martha’s Vineyard.

Driving Info: 68 miles, 1 hr 35 minutes

Days 21 – 23 Falmouth to Martha’s Vineyard, Massachusetts

Just south of Cape Cod and a short ferry ride away sits Martha’s Vineyard, a presidential getaway in my mind. I picture snazzy inns, upscale boutiques, and perfect stately homes; ritzy glamour degraded by the simplicity of the beach… where I will tell no one that our minivan turned campervan awaits us back on the mainland. Read here about all the fun things to do on Martha’s Vineyard Island. 

Driving Info: 19 miles, 1 hour 15 minutes with a ferry ride

Day 24: Martha’s Vineyard to Plymouth, Massachusetts

Advancing north, stop for an overnight at the first Pilgrim settlement, Plymouth, where I’m sure you will have mixed emotions about the small rock that marks the spot.

But the iconic landmark is not what keeps visitors coming back for more.

Driving Info: 55 miles, 2 hrs

Day 25: Plymouth to Salem, Massachusetts

If you haven’t heard of the Salem witch trials then you may be living under a rock. Plymouth rock, perhaps.

Salem is not shy about its history where the word “witch” is displayed all over town. It shouldn’t come as a surprise that a witch museum, cemetery and a house with a supernatural past are on our itinerary.

Driving Info: 64 miles, 1 hr 17 minutes

Day 26: Salem, Massachusetts to Hampton Falls, New Hampshire

Clutching the coast, swing past Manchester-by-the-Sea, Gloucester, Rockport, and Newburyport before crossing over to the next state of New Hampshire.

Make sure to detour to the Hammond Castle Museum, an exotic castle built in the early 1900s by an inventor.

Driving Info: 32 miles, 45 minutes

Day 27: Hampton Falls, New Hampshire to Kennebunkport, Maine

At 18 miles long, New Hampshire’s coastline is short-lived so progress to the state of Maine. It’s hard to believe you’ve hit five of the six New England states already!

Kennebunkport is going to be all about seafood, boats, and shopping.

Driving Info: 43 miles, 50 minutes

Days 28 – 35: Kennebunkport to Acadia National Park, Maine

It’s time for some hiking and biking! Park it in Acadia National Park for at least four days (more if you can swing it) because you’ll be in awe of the beauty around you.

Cadillac Mountain, Sand Beach, Bar Harbor, and Park Loop Road are just a few things on the list of things to see. 

Read about one of the most thrilling hikes in the Northeast that you’ll find within the park. 

Driving Info: 201 miles, 3 hrs 30 minutes

Days 36 & 37: Acadia National Park to Bangor, Maine

The main reason for our weekend in Bangor is to visit with friends, but items like a Stephen King’s house and the world’s largest Paul Bunyan statue might have you putting it on your itinerary as well.

Driving Info: 50 miles, 1 hr 15 minutes

Days 38 – 40: Bangor to Baxter State Park, Maine

Baxter State Park is home to Mount Katahdin and the end of the 2,168-mile Appalachian Trail. Take a few days to explore and hike to the peak of the highest mountain in Maine at 5,270 feet.

Driving Info: 88 miles, 1 hr 35 minutes

RELATED: SEE OUR FAVORITE FREE CAMPING APPS

Days 41 & 42: Baxter State Park to Lily Bay State Park, Maine

At Lily Bay State Park, you’ll find what’s often referred to as Maine’s crown jewel, Moosehead Lake, the largest lake in New England.

It is also known to sprout some bright fall colors and is a great area to spot moose.

Driving Info: 51 miles, 1 hr 35 minutes

Days 43 – 48: Lily Bay State Park, Maine to White Mountains, New Hampshire

The Kancamagus Highway, a 34-mile road through the heart of the White Mountains, is one of the best drives for fall foliage in the United States.

No stores, no houses – just forest; the scenic byway stretches from Lincoln to Conway.

Driving Info: 205 miles, 4 hrs 25 minutes

Days 49 & 50: White Mountains to Burlington, Vermont

Along the shores of Lake Champlain sits a vibrant city with a thriving arts scene and welcoming atmosphere. Vermont’s largest city, Burlington, has a little bit of everything.

Driving Info: 2 hrs 20 minutes

Days 51 & 52: Burlington to Stowe, Vermont

The birthplace of the infamous Heady Topper Beer from The Alchemist Brewery and a stone’s throw away from Ben & Jerry’s factory, I think I’m going to start calling Stowe, the adult playground of Vermont. 

Driving Info: 36 miles, 46 minutes

Days 53 – 59: Stowe to West Dover, Vermont

From Stowe, take the well-known Highway 100, another popular fall foliage route in New England, down along the Green Mountains.

Hopefully, those green mountains will be lit up with scarlet reds, glistening golds, and tangerine orange.

Driving Info: 147 miles, 2 hrs 41 minutes

Day 60: West Dover, Vermont to Chicago, Illinois

At this point in the trip, you could take an extra night to stop at the one and only Niagara Falls in New York. Otherwise, that’s a wrap folk!

60 days and a whole lotta unforgettable memories!

TIP: For those of you that would like to close the loop, head further south to the Berkshires of Western Massachusetts. A popular destination for fall foliage, cultural attractions, and outdoor fun. 

Driving Info: 13 miles, 13 hrs 36 minutes

See Below for a Map of the New England Road Trip Itinerary.

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Do you have any additions to our New England road trip itinerary? Let us know in the comments below!

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• About Author
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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

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13 Responses

So, I’m a fan of this trip. You had me at Gilmore Girls, Mystic Pizza and then solidified how much we are connected with Salem and Bangor.

I have wanted to do a Fall Foliage trip like this forever. I think I might try to make this happen one year…soon. I can’t wait to see your photos on the IG.

Dang Travelers

It has been on our list of places to get to for awhile now so we are ecstatic to finally be making it happen. I’m cracking up because when I (Angela) was making the itinerary I totally watched a few Gilmore Girls episodes and the movie, Mystic Pizza to get pumped! Leaving the GG reference out to Save though. He didn’t know that’s why I planned that area until a few days ago! LOL We will get started on all your planning so all you have to do is find the time. Thanks for following Kristi!

You didn’t include Mt. Washington and the cog railway. You should try to hit they in!!! I think you’re gonna love Block Island, Burlington, Acadia. The coast of ME. Mystic is nice. Portsmouth, RI has a ride the rails along the waterfront. Check that out. Too bad you are missing Boston!

We will be hitting Mt Washington in the White Mountains but didn’t know about the cog railway! So excited to explore Rhode Island and Connecticut or shall I say #47 and #48 of my states list. Dave really wanted to go into Boston but figured we could do it on another trip when we fly in. Always expensive and difficult to worry about parking in big cities but othwrwise we would have loved to. Thanks for the tips Cheryl!

Your trip sounds awesome. I cannot wait for all the pictures and to hear all about it. I would make a detour in Maine and stop in Freeport, Maine and go to LL Bean store. It is an absolute must see. It is open 24 hours (at least it used to be) and there are 9 floors and each one is better/more exciting then the next. It isn’t just clothes either. My husband enjoyed it as well and he isn’t a shopper.

Top Things to Do on Block Island: A Travel Guide – Dang Travelers

[…] SEE OUR ENTIRE 60 DAY ITINERARY […]

Found your trip itinerary and will definitely be putting it to use! Not too often do you find trips starting in the Midwest! I just went through and copied and pasted all the trip info you suggested. Or is there a printable version of this that I completely missed somewhere? Thanks so much for sharing!

Hi Nicole! I do not have a downloadable itinerary as of right now. Sorry, hopefully copying worked just fine. You’ll love it out east!

Cheryl Archambault

For anyone wanting to specifically see the foliage start in farthest north of New Hampshire generally around the 3-4 week of September. Foliage is peak around Concord during Columbus Day Weekend; but cool or rainy weather can change that. Encourage you to take a jacket and go up the Cog Railway to the top of Mt. Washington. It could be covered in snow there! In Rhode Island Block Island is lovely. Ferries leave from Pt. Judith or Newport. Newport is lovely and don’t miss seeing Waterfire in Providence. Acadia National Park and Bar Harbor and Boothbay is wonderful. East to west Vermont in Fall is a dream. Rte2 is a very scenic ride.

Thanks so much Cheryl!

my husband & I want to do an abbreviated version of your trip. What time of year did you do this trip? I have heard Sept is the best time for lobster but Oct is the best time for foliage.

We started right after labor day in September but took about 3 months. That year the fall color was starting to come in late September and lasted through the third week of October. Inland and lower elevations started earlier with Acadia National Park at peak around the second week of October. Unfortunately, every year is different so it’s hard to get it just right when planning ahead of time!

Thank you for the itinerary. It is a great start for me. I don’t have quite as much time but I hope I can get to a lot of the highlights as I’m starting from Virginia.

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2-Week Northeast Coast Road Trip Itinerary For Families: NYC To Acadia National Park

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Get excited for this 2-week Northeast Coast itinerary for families from NYC to Maine! Whether you want to hike in Acadia National Park or see the iconic attractions of NYC, this article covers some of the best places for families on the Northeast Coast. Kids will love hiking through scenic landscapes, visiting fun museums, or stopping for dessert at iconic mom-and-pop shops. You can also choose a few of these places to stop during your road trip or you can separate this itinerary into different vacations. Either way, we’ve gathered a list of things to do with kids, as well as where to stay and other tips for taking a Northeast Coast road trip with kids. Keep reading to plan your next epic adventure with kids on the road! 

Day 1: New York City (Midtown Manhattan)

Of course, New York City is an iconic start on any Northeast Coast road trip itinerary for families! If you only have a few days to see the city, we recommend at least three to stop at all the highlights. 

Midtown Manhattan is a hotspot for shopping and entertainment, so we definitely recommend a little bit of both! Kids will love the toy shops located around Rockefeller Center, like FAO Schwarz . If your child has an American Girl Doll or wants one, you can’t miss the American Girl Place . Meanwhile, gamers can visit The Lego Store on 5th Avenue or the Nintendo Store . Parents will find plenty of luxury stores on 5th Avenue, ranging from Saks to Versace. 

Afterward, see a local show in Midtown. Of course, the area is famous for Broadway , which boasts kid-friendly classics such as The Lion King and Frozen. To see a more casual show, buy tickets for The Gazillion Bubble Show . Young kids will love this interactive spectacular! If you want somewhere to eat a late breakfast or lunch, Ellen’s Stardust Diner, which features a singing waitstaff, is a favorite among families. 

Additional/Alternate Activity: Visit Famous NYC Landmarks

Instead of shopping on your Northeast road trip itinerary for families, you can see some of New York City’s famous landmarks. Start on 34th Street and 5th Avenue at the Empire State Building for a 360-degree city view. Families can even book a Premium Historical Tour to get a better look at the behind-the-scenes.

Then, go to Bryant Park , which offers family fun no matter the season. You can go ice skating in the winter, visit the Christmas market, or ride Le Carousel . Nearby, there’s the main branch of the New York Public Library. Even if you don’t go inside, appreciate the sheer size of the ornate building. Kids can take pictures with the lion statues! Afterward, you’re just a few blocks from Times Square , an attraction for all ages. Little kids will love all the flashing lights and the opportunity to meet their favorite characters like Elmo or Mario! 

Purchase your CityPass NY here as it will give you discounted admission to the Empire State Building!

Looking for more NYC inspiration? Read this Exciting 7-Day NYC Itinerary With Kids of All Ages .

Day 2: New York City (Upper West Side or The Battery)

Manhattan’s Upper West Side is the next stop on our Northeast road trip itinerary for families with kids! First, head to the American Museum Of Natural History , a must-visit for young or elementary school-aged children. Kids will love looking at the dinosaur fossils, watching stars twinkle in the Hayden Planetarium , and seeing the giant blue whale in the main area!

Children who want to challenge their creativity can’t miss the Children’s Museum of Manhattan on West 83rd Street between Broadway and Amsterdam Ave. Here, you’ll find a variety of hands-on exhibits, as well as an outdoor section. History buffs may also fancy a visit to the New York Historical Society. Inside, you’ll find a special section dedicated to kids between the ages of eight and thirteen called the DiMenna Children’s History Museum.

Parents with younger kids may want to consider seeing a show at the Swedish Marionette Theater on 79th Street and Central Park West. 

Additional/Alternate Activity: The Battery

Want to enjoy quality time by the waterfront? Head to The Battery , formerly known as Battery Park. Kids will love taking a spin on the Seaglass Carouse l or cooling off in the Bosque Fountain!

The Battery is also an access point for boats going to The Statue of Liberty , so it’s ideal for families who want to see both places. About a fifteen-minute walk away, you can visit One World Trade Center, and then the 9/11 Memorial Museum. It may not be a suitable stop on an NYC itinerary if you have young kids, but older kids will appreciate it.

Additional/Alternate Activity: SoHo

SoHo is known for its shopping, culture, and incredible dining scene. Shops like Adidas , The North Face , and Uniqlo are usually popular with families. Little ones will also love getting their hands dirty at the Sloomoo Institute , where they can touch different kinds of slime and even make their own. Of course, nothing says interactive museum quite like the Museum Of Ice Cream ! 

Day 3: New York City (Upper East Side + Central Park)

If you have teens who love art or history, Museum Mile is a must when visiting NYC with kids. Spanning 82nd Street to 105th Street along 5th Avenue, this crowded stretch is famous for its string of world-class institutions. Of course, you should start with the Metropolitan Museum of Art , also known as the largest museum in the United States. You can see anything from Egyptian artifacts to modern art in its huge collection!

Meanwhile, European art is in abundance at the Neue Galerie New York . Get your daily dose of modern art at the Solomon R Guggenheim Museum . Then, see art in an upscale mansion at the Frick Collection . Or, visit the Jewish History Museum. Families can also visit El Museo Del Barrio on 104th Street to learn more about New York’s diverse culture. Nearby, The Museum of the City Of New York gives a great backstory on the city. 

Additional/Alternate Activity: Central Park

If you have extra time on your Northeast road trip itinerary for families, visit Central Park . It’s huge, so you could easily keep exploring beyond what we’re mentioning here. Or, combine a trip to Central Park with the Upper West Side – there are multiple entrances near 79th Street and 64th Street and Central Park East. Of course, kids will adore the Central Park Zoo , home to a Snow Leopard section, a Grizzly Bear Overlook , and a Polar Circle , among other habitats. Also located along East 65th Street, ride the famous Central Park Carousel . 

Want to visit a playground with your kids? Head to the Ancient Playground near East 86th St and 5th Avenue, the Billy Johnson Playground near 67th Street, or the Heckscher Playground on 65th St.

Additional/Alternate Activity: Brooklyn Bridge

The Brooklyn Bridge is an iconic NYC attraction! Though many people choose to start on the Brooklyn side and proceed to Manhattan, you could do the opposite. You’ll still get the same great views, but with fewer crowds, as you make your way to Brooklyn. 

Once you reach the other side, stop at Brooklyn Bridge Park to overlook the waterfront. Here, you’ll find playgrounds for kids, the Environment Education Center , and Jane’s Carousel. Then, you can walk around Dumbo, and maybe take a picture on the iconic Washington Street with the bridge in the background. If you’re hungry for a bite to eat, visit Grimaldi’s Pizzeria for a brick oven pie. 

Where to Stay in New York City with Kids

In Lower Manhattan, we recommend the Millennium Downtown New York Hotel or the trendy Greenwich Hotel . In Midtown Manhattan, try the Loews Regency New York , Omni Berkshire Place , or the St. Regis New York . Remember to check out other NYC hotels with pools and spacious suites. NYC also has lots of affordable Vrbos in and around the outer boroughs.

Day 4: Newport, Rhode Island

Distance from nyc to newport: 3 hours.

Continue your adventure in Newport, Rhode Island, known for its luxurious mansions, seaside views, and delicious seafood! It’s around three hours from NYC in the car, and then you’ll be less than 1.5 hours away from Boston. 

For breakfast, we recommend Hungry Monkey , a local favorite known for its classic diner fare and friendly service. Then, start your morning by touring one of Newport’s many luxurious mansions, like The Breakers or The Elms . Kids will marvel at the grand architecture and lavish interiors while learning about the history of Newport’s elite families.

After touring the mansions, take a stroll along the Cliff Walk. This scenic trail follows the coastline for 3.5 miles, offering breathtaking views of the Atlantic Ocean and passing by several historic landmarks, including The Breakers and Rough Point. Pack a picnic lunch to enjoy at one of the designated picnic areas along the trail. If it’s warm when you visit, you could also spend the afternoon at Easton’s Beach . (Kids will also love riding the vintage carousel!)

Afternoon Activity: Newport Harbor

Families can spend the afternoon in the Newport Harbor area on a sailing cruise. Several companies offer family-friendly sailing excursions that provide an unforgettable experience on the water, with opportunities to see historic lighthouses, marine wildlife, and beautiful coastal scenery. 

Then, visit the Tennis Hall of Fame & Museum , which celebrates the history of tennis through interactive exhibits, memorabilia, and a Hall of Fame gallery showcasing the sport’s greatest players. Kids can test their skills on the outdoor grass courts or try their hand at virtual tennis simulations! 

Evening Activity: The Black Pearl, Thames Street

For dinner, head to the Newport waterfront and dine at The Black Pearl. This iconic restaurant offers fresh seafood and New England classics in a charming setting overlooking Newport Harbor. Try their famous clam chowder or lobster roll for a taste of local cuisine.

To end your night, walk along Thames Street, Newport’s main thoroughfare lined with shops, boutiques, and art galleries. Stop by Ben & Jerry’s for some delicious ice cream or treat kids to a trip to Newport Creamery or Newport Fudgery ! 

Here are 16 Fantastic Northeast Coast Summer Destinations Families Will Love !  

Day 5: Boston, Massachusetts (New England Aquarium, Freedom Trail, North End)

Distance from newport to boston: 1.5 hour.

Spend at least two days of your Northeast Coast road trip itinerary for families in Boston, known for its historical attractions, museums, and fantastic food! It’s around an hour and a half from Newport, plus it’s near our next stop on this trip, Salem. 

Fuel up for the day with a delicious breakfast at Mike’s City Diner , a beloved local spot known for its classic American breakfast fare. Then, check out the New England Aquarium. Kids will love the various exhibits showcasing marine life from around the world, including the Giant Ocean Tank, home to a vibrant coral reef and a variety of tropical fish. After the aquarium, stroll along the scenic Boston Harborwalk. Enjoy views of the waterfront and watch the boats sail by as you make your way to Quincy Market for lunch! 

Afternoon Activity: Quincy Market, Boston Tea Party Ships & Museum

For lunch, families can explore the food stalls at Quincy Market to eat anything from lobster rolls to pizza. After lunch, head to the Boston Tea Party Ships & Museum. Here, you can step back in time to December 16, 1773, and relive the events leading up to the Boston Tea Party through interactive exhibits and live reenactments. Kids can even participate in tossing tea overboard from a replica tea ship! 

You can also walk the Freedom Trail , a 2.5-mile-long path that passes by 16 significant historic sites in Boston, including Boston Common and the USS Constitution Museum . Eventually, you can make your way to the Paul Revere House in the North End, stopping at landmarks like the Massachusetts State House and Faneuil Hall along the way.

Evening Activity: Dinner In The North End

For dinner, head to the North End, Boston’s historic Italian neighborhood, and dine at Giacomo’s Ristorante. This cozy trattoria is known for its delicious pasta dishes and generous portions, perfect for hungry families. After dinner, indulge in some homemade gelato from one of the nearby gelaterias. 

Don’t miss adding these 25 Amazing Things to Do in Boston with Kids to your itinerary!

Day 6: Boston, Massachusetts (Museum of Science, Charles River Esplanade, Beacon Hill)

For breakfast on the second day of your Boston itinerary for families, head to Flour Bakery + Cafe , a local favorite known for its freshly baked pastries and gourmet sandwiches. After, spend the morning at the Museum of Science.  With interactive exhibits covering topics like biology, physics, and space exploration, there’s plenty to keep both kids and adults entertained. Grab a quick bite to eat at the museum’s café or pack a picnic lunch to enjoy by the Charles River Esplanade.

Afternoon Activity: Boat Ride Along The Charles River

After lunch, take a boat cruise along the Charles River. Several companies offer sightseeing cruises that provide stunning views of the Boston skyline and iconic landmarks like the Prudential Tower and the Longfellow Bridge. Alternatively, for a distinctive experience, try a Duck Tour , which offers a combined land and water journey. These amphibious vehicles traverse both the historic streets of Boston and then splash into the Charles River, providing a fun and informative tour that highlights the city’s rich history and unique architecture.

. Once you’re done, you can explore Boston’s historic neighborhoods on foot, like Beacon Hill and Back Bay . Admire the elegant brownstone homes, stroll through the picturesque Public Garden, and window shop along Newbury Street.

Evening Activity: Seaport District 

For dinner, head to Legal Sea Foods in the Seaport District. This iconic Boston seafood restaurant offers a wide selection of fresh seafood dishes, including lobster, clam chowder, and oysters. After dinner, take a stroll along the Harborwalk to enjoy the twinkling lights of the city skyline reflected in the water.

Where To Stay In Boston With Kids

Boston has plenty of family-friendly hotels! For the most convenient locations, stay at the Fairmont Copley Plaza , the Kimpton Nine Zero Hotel , or the Boston Marriott Long Wharf. All boast kid-friendly amenities such as pools and are located in close proximity to the city’s best attractions. For more suggestions, consult our list of the best hotels in Boston for families ! 

Day 7: Salem, Massachusetts

Distance from boston to salem: 1 hour.

Before making your way to Maine, you can make a pit stop in Salem and stay somewhere nearby for one night. Famous for its 17th-century Witch Trials, kids will love witnessing the place where this historical event happened. Plus, it’s less than an hour away from Boston. 

Eat breakfast at Red’s Sandwich Shop , a cozy diner known for its hearty breakfast options and friendly service. Try their fluffy pancakes or classic bacon and eggs to fuel up for a day of exploration! Then, your first activity can be the Salem Witch Museum. This family-friendly museum explores the Salem witch trials of 1692 through life-size stage sets, figures, and narration that’ll impress kids. At Salem Common , kids can run around on the playground or relax on the grass while taking in the scenery.

Afternoon Activity: Walking Tour, Peabody Essex Museum

For lunch, head to the Salem waterfront area and grab a bite to eat at the Lobster Shanty.   Then, you can also take a walking tour of this charming town, where you will learn all about its sordid history in spooky detail. Families can even choose from themed tours, like a h aunted history tour, which offers a fun and informative way to learn about Salem’s spooky legends. 

After the tour, visit the Peabody Essex Museum , one of the oldest and most prominent art museums in the United States. The museum’s diverse collection includes art and artifacts from around the world, as well as interactive exhibits and activities for kids. For dinner, head back into town and dine at the Flying Saucer Pizza Company.  

Evening Activity: Salem Witch Trials Memorial

You can wrap up your day in Salem with a visit to the Salem Witch Trials Memorial , located next to the Old Burying Point Cemetery. This peaceful memorial honors the innocent victims of the witch trials and provides a quiet place for reflection and remembrance. Or, stroll along the waterfront to enjoy the evening views of the harbor.

Where To Stay In Salem With Kids

Families looking for a truly spooky stay in Salem can book a room at the Salem Inn , which is allegedly haunted! Or, check out Vrbo for more options. Plus, did you know that Salem is one of the 13 Best Places to See Fall Foliage in New England with Kids ?

Day 8-11: Coastal Maine (York, Ogunquit, Portland)

Distance between salem and york: 1 hour.

After departing from Salem, families can explore the beauty of coastal Maine on a Northeast road trip itinerary. It takes around 1 hour to reach York, Maine from Salem, and the drive is very scenic. 

Spend time sunbathing, strolling the shore, or trying water sports on Long Sands Beach . It also provides fantastic views of the Cape Neddick Nubble Lighthouse . Active families can also enjoy a beautiful hike at Mount Agamenticus, offering trails for all skill levels. Even little ones will be able to handle the 1.9-mile Ring Trail Loop, featuring a great view of Maine’s coastline. Animal enthusiasts can’t miss the chance to visit York’s Wild Kingdom Zoo and Fun Park!  

Distance Between York and Ogunquit: 10 Minutes

Ogunquit is a charming town on Maine’s southern coast. With sandy beaches, cultural activities, and multiple tasty restaurants, it’s a great place to stop on a Northeast Coast itinerary for families. 

Lounge on the gorgeous Ogunquit Beach, which is large, clean, and bustling. Families can also sightsee on the Ogunquit Trolley or stroll the famous Marginal Way , a mile-long scenic cliff walk . Eventually, you’ll come upon the small fishing village of Perkins Cove . Families can also visit the Ogunquit Playhouse . If you have extra time on your vacation, consider visiting the Ogunquit Museum of American Art , taking a Finestkind Scenic Cruise , or heading to Footbridge Beach.

Distance Between Ogunquit and Portland, Maine: 45 Minutes

In Portland, families should take a Maine Lobster Boat Tour, available through vendors such as Lucky Catch Cruises , Rocky Bottom Tours , and Casco Bay Custom Charters . Fishing lovers can also take a trip to nearby Cliff Island, accessible via the Casco Bay Island ferry from Portland’s harbor. Or, head to Mackworth Island State Park , located in Falmouth adjacent to Portland. Shopping enthusiasts will be impressed by the selection at the Freeport Outlets just north of the city, where you can find great deals on a variety of luxury stores. 

Where To Stay In Maine With Kids

Maine offers families plenty of kid-friendly accommodations. If you’re staying near Ogunquit, families love Cliff House Maine in Cape Neddick. Or, the Beachmere Inn , a Cape-Cod-style hotel overlooking the ocean. 

Day 12: Acadia National Park (Park Loop Road, Jordan Pond)

Distance between portland, maine and acadia national park: 3 hours.

Acadia National Park is a great place to end your Northeast Coast road trip itinerary for families! Located near Bar Harbor, we suggest spending at least two full days in the park, but you can fit the highlights into one day if you’d like. 

Grab a hearty breakfast at Jordan’s Restaurant – the blueberry pancakes are a favorite among locals and tourists alike! After, you can head to the Visitor Center to pick up a map and get oriented with the park. Then, drive the Park Loop Road , making stops at popular sights like Thunder Hole, Sand Beach , and Otter Cliffs. These spots offer stunning coastal views and easy walks suitable for families with kids.

Afternoon Activity: Picnic Lunch and Jordon Pond Path

Then, have a picnic lunch at one of the designated picnic areas along the Park Loop Road. Once you’re done eating, you can take a hike around Jordan Pond on the Jordan Pond Path. This flat, 3.3-mile loop offers beautiful views of the pond and surrounding mountains, with plenty of opportunities for kids to skip rocks and explore. 

Day 13: Acadia National Park (Cadillac Mountain, Biking the Carriage Roads)

Get an early start to beat the crowds at Cadillac Mountain and watch the sunrise from the highest point on the eastern seaboard. The 4.4-mile Cadillac North Ridge Trail has sweeping views of Bar Harbor, Frenchman Bay, and the Schoodic Peninsula. After sunrise, enjoy breakfast at Jeannie’s Great Maine Breakfast , a cozy spot known for its delicious breakfast options and friendly service.

Afternoon Activity: Biking, Bubble Pond

After lunch, families can explore the carriage roads in the park. They offer miles of car-free paths through the park’s wooded landscapes, perfect for a family bike ride. Rent bikes from one of the rental shops in Bar Harbor or bring your own. Then, stop for lunch at Jordan Pond House Restaurant again or pack a picnic to enjoy along one of the carriage roads. After lunch, take a short hike to one of the park’s many picturesque ponds, such as Bubble Pond or Witch Hole Pond.

Evening Activity: Bass Harbor Head Lighthouse

Wrap up your trip with a visit to the Bass Harbor Head Lighthouse. The 0.4-mile trail to the lighthouse offers stunning views of the rugged coastline and is a great spot for family photos. For dinner, head back to Bar Harbor and be sure to try some fresh lobster or other local seafood specialties before saying goodbye to Acadia National Park!

Where To Stay Near Acadia National Park

For first-time visitors, Bar Harbor is a great place to stay near Acadia National Park on your Northeast road trip itinerary for families. From here, you can easily visit some of the park’s best attractions. There are hotels, Vrbo , and camping options in Bar Harbor.  

Happy Travels!

We hope you liked this 2-Week Northeast Road Trip Itinerary For Families! From Acadia National Park to NYC, there are plenty of ways to make your trip special and memorable. Enjoy your next Northeast road trip itinerary for families on vacation! 

*This post may contain affiliate links that may earn us a small commission, at no additional cost to you. Affiliate links in no way inform the hotels, sights, products, or other recommendations included in our articles. All opinions and recommendations expressed here are compiled from submissions submitted by the generous members of our Families Who Love To Travel community.

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Enjoy the Best Northeast USA Road Trips This Year

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When it comes to exploring the very best of the United States, there is no better way to accomplish this than by taking an epic road trip. We LOVE packing our car with the essentials and then heading out on a long weekend road trip to enjoy new parts of the US. From the east coast to the west and everything in between, the US is the perfect location and epitomizes everything there is to love about road trips. If you read our post on the best east coast road trips , you will know that we are very fond of the New England corridor. What better way to celebrate this beautiful part of the country than by highlighting the very best northeast USA road trips.

We are grateful to a collection of our friends in the travel blogging world for contributing to this epic post. We have been fortunate to enjoy a couple of amazing road trips in northeast USA over recent years, but when it comes to putting together a post highlighting the “best of the best”, we figured it was appropriate to call in the experts. Let’s take a look at some of the best road trips you can experience this year and of course, in years to come.

Best Northeast USA Road Trips

Whether you are exploring the neighborhoods of Boston or heading along the coast to explore the iconic lighthouses near Portland, the New England area is the perfect spot to enjoy a spectacular road trip. Breathtaking fall foliage, picturesque wintry scenes, gorgeous national parks and much more typify why this part of the US is such a popular region for road tripping.

Here is a collection of road trips that we are going to highlight throughout the post but this is just a small sample of the myriad of endless opportunities that exist in the American northeast.

• Boston to Montreal – In 2014, we took a similar road trip from Boston to Quebec taking in all of the states in this part of the country before crossing the border into Canada.
• Providence to Newport (Rhode Island)
• Boston Figure of Eight – Cape Ann, Salem, Plymouth, Cape Code etc.
• Scenic Route 100 Byway (Vermont)

Boston to Portland

Portland to acadia national park, new york city to cape cod.

• Hudson River Valley – head a little further inland from the New England corridor and the state of New York offers a collection of amazing road trip options, including this epic journey.
• Finger Lakes (New York) – this is the “exception” to this list of New England road trips but it’s a short distance from this region offering spectacular scenery and so well worth including in this post.

Boston to Montreal

Click here to open Google Maps for details of this road trip between Boston and Montreal

On your way to Montreal drive up to New Hampshire and into the white mountains. Pull off the road to enjoy the views, hikes, and waterfalls of New Hampshire. If you have kids along enjoy Santa’s Village or Storyland and the cute ski town of Lincoln. 

Take time to placate your sweet tooth with the world’s longest candy counter at Chutter’s in Littleton. Right before you reach the Canadian border you will find the Derby Line – you are halfway between the North Pole and the equator! You can even cross the border by walking through a library. This is the kind of kitschy stuff road trips are designed for. 

After visiting Montreal, head back to Boston through the artistic, rural state of Vermont. Take a tour at the Ben and Jerry’s Ice Cream Factory. Stop by the most charmingly New England town of Woodstock where you can shop, walk the town green and see its covered bridge. Also, stop by the nearby artists’ studios and farms; Hike the famous Quechee Gorge to see the best of fall’s colors. This drive will take about 10 hours and is the perfect way to experience New England.

Thanks to Jamie Italiane from The Daily Adventures of Me for sharing this awesome road trip. Read on for more details about this  road trip from Boston to Montreal .

Providence to Newport

Click here to open Google Maps for details of this road trip between Providence and Newport, Rhode Island

New England is filled with history and great outdoors experiences, providing a plethora of travel opportunities to fit any nomad’s preference. But during the fall, the North Eastern coast of the United States erupts in beautiful hues of orange, brown, and every autumn shade imaginable. 

More specifically, Rhode Island acts as a perfect example of what the North East has to offer, and a short road trip from Providence to Newport allows you to take it all in. This is a short trip taking you through the more rural regions of Rhode Island and allowing you to take in all the foliage. 

Your destination in Newport is where the fun begins, with some of the best seafood and eateries that you’ll find in the U.S., such as the Red Parrot Restaurant. 

When you decide to eat is on you, but maybe you’d prefer to explore the mansions on the Newport shores first? Regardless, be sure to take in both no matter how you plan it, as nothing beats an autumn scenic drive ending in engorging seafood and amazing architecture!

Thanks to Casey LaClair from Viraflare for sharing her thoughts on this scenic road trip in Rhode Island.

Boston Figure of Eight

Click here to open Google Maps for details of this road trip around the iconic locations in Massachusetts

Boston offers so many intriguing road trips that the best thing to do is to loop a few together in a figure of eight on a map. Start by heading north to Cape Ann, the quieter side of New England. Look for breezy promenades, squat light houses and the home of deep fried clams.

Return to Boston, stopping in at Salem to look at the witch trials that featured in Arthur Miller’s The Crucible, then continue south. Stay overnight in Plymouth and grapple with the history of the Mayflower and the arrival of the pilgrims amid tranquil marinas and polished lawns.

From there continue into the hook of Cape Cod, her salty sand banks and calm waters. If time allows, take the ferry to Martha’s Vineyard and Nantucket, two different glimpses of life in America, each with their own charm.

Finally, return to Boston, with a quick detour to see the deep blood red of the cranberry bogs that lie along the side of the road. For further details on this journey, check out this road trip from Boston .

Thanks to Abigail King from Inside the Travel Lab for sharing this road trip featuring some of the best things to do in the state of Massachusetts.

Scenic Route 100 Byway

Click here to open Google Maps for details of this road trip along Scenic Route 100 in Vermont

There are endless opportunities for road tripping in Vermont. The state has more dirt roads than paved and more cows than people. Route 100, which is Vermont’s longest state highway, runs 216.6 miles through the Green Mountains, from north to south. If you’re looking for a quintessential Vermont road trip, then Route 100 is the perfect place to start. 

Begin your journey in the small mountain town of Wilmington and head north through the Green Mountain National Forest. The road passes pristine mountain lakes, cascading waterfalls, secret swimming holes, and quite campgrounds. It is an awesome Vermont road trip for fall when you can take full advantage of the gorgeous fall colors and outdoor adventures in the mountains. 

Highlights of a Route 100 road trip include Jamaica State Park, where you can rent a cabin on the West River, the iconic Long Trail Brewing Company in Bridgewater Corners, and the beautiful mountain town of Stowe. Be sure to drive up the Mt. Mansfield Toll Road at Stowe Mountain Resort. At 4,395 feet, Mt. Mansfield is Vermont’s tallest peak, and the views from the top are incredible. 

After 216 miles of driving, Route 100 ends in the bustling little city of Newport, where you can take a sunset cruise on Lake Memphormagog, eat traditional Thai food at Dusit Thai Cuisine, and shop the local boutiques on Main Street.

Thanks to Tara Schatz from Back Road Ramblers for highlighting some of the lesser known spots worth exploring in the New England area in the state of Vermont .

Click here to open Google Maps for details of this road trip along the New England coast between Boston and Portland

Many have heard of Salem, Massachusetts because of its’ haunted history of witchcraft hysteria in the 1690s and witch trials. With hundreds of thousands of visitors every year, there is no doubt that this is a must on your road trip from Boston, Massachusetts to Portland, Maine.

With many haunted happenings no matter the time of year, the best time to visit Salem is in the fall for the biggest effect. No visit to Salem would be complete without visiting at least one of the following three attractions. The Witch History Museum is where to go to hear all the stories of witch trials and witch craft in Salem. 

Following your visit to the museum head to the Witch House, which is the only building in Salem still standing with direct ties to the Salem Witch Trials. The house was owned by Judge Jonathan Corwin who was the judge of the Salem witchcraft trials. It is believed that some interrogations even took place here!

On a less spooky note, Salem is also home to Nathanial Hawthorne’s “The House of the Seven Gables” which offers tours and gives you a picture into what life was like in the 1800s. Salem is a culturally rich and haunted gem of the USA definitely worth your time. 

Thanks to Sarah Fay from Travels of Sarah Fay for highlighting why the iconic town of Salem is a must-see during your road trip from Boston to Portland. When you arrive in Portland, don’t forget to explore the historic Portland Head Light along with other lighthouses along this stretch of coastline.

Click here to open Google Maps for details of this road trip from Portland to Acadia National Park along the coast of Maine

If there’s one thing Maine is definitely good for its road trips and after road-tripping the entire Maine coastline, I’d highly suggest driving from Portland, Maine to Acadia National Park in Maine. There are plenty of things to do along the way, plenty of sites to see, places to eat, and much more that you could spend weeks along this route and still not see it all. But, of course, there are always highlights. 

Starting in Portland, make sure to check out one of the most beautiful lighthouses, Portland Head Lighthouse, eat at Green Elephant in the city, grab donuts at Holy Donuts, and walk around Mackworth Island. 

Next stop is Damariscotta to grab a bit and check out the small town before heading to Pemaquid Lighthouse (make sure to go up in the lighthouse – it’s one of the few you can!). Then head to Marshall Point Lighthouse to see the lighthouse from Forrest Gump! 

Keep heading along the coast stopping in Rockland for cool street art, shopping and restaurants and then head up to Camden Hills State Park for beautiful, panorama views and hiking. The last leg of this road trip includes a stop in Deer Isle for a unique and off the beaten path vantage of Maine – drive around the entire island making leisurely stops along the way and soak up what feels like a step back in time – and a stop in Bangor to scope out all the cool Stephen King locations and a cool, sleepy New England town.

While in Acadia National Park, make sure to check out all the amazing hikes (I highly suggest the Wonderland and Ship Harbor Trail), take day trips to Bar Harbor to explore this adorable town and take a whale watching tour, and go kayaking around the many little islands. 

Thanks to Ashley Hubbard from Wild Hearted (also, Oddities and Curiosities) for sharing this amazing road trip along the Maine coastline.

Click here to open Google Maps for details of this road trip along the coast of Connecticut, Rhode Island and Massachusetts

A road trip from New York City along the coastline of Connecticut, Rhode Island and the Cape Cod section of Massachusetts in the autumn is a great idea because the weather is still pretty warm yet the crush of the summer tourist season is finished. Autumn color blooms along this route by mid-October as well. 

There are quite a few historical places to visit on this road trip. In Connecticut be sure to visit New Haven which is famous for Yale University (and Louis Lunch which is the reputed birthplace of the hamburger) and Mystic which has a renowned aquarium and living history museum. Mystic skyrocketed to fame in the 1980’s for the movie, Mystic Pizza, which was one of Julia Roberts’ first major hits. Mystic Pizza still exists and is totally worth a visit. 

In Rhode Island, be sure to stop off in Newport and visit the summer “cottages” of the super rich elite of the Gilded Age. Newport also has a charming harbour and is home to the International Museum of Tennis. 

In Cape Cod and the Islands ( Martha’s Vineyard and Nantucket), you will find autumn is a great time for cycling, hiking, and fishing – pretty much every outdoor activity available during the more expensive summer months except for beach going.

Make sure not to miss the cranberry bogs in the area as well. Some of the local fall festivals include the famous Wellfleet Oyster Festival, Oktberfest in Chatham or the Martha’s Vineyard Food and Wine Festival in Edgartown.

Thanks to Shobha George from Martha’s Vineyard Tourist for sharing this awesome road trip along the New England coastline.

Hudson River Valley

Click here to open Google Maps for details of this road trip along the Hudson River Valley

When it comes to fall leaf-peeping destinations, New England tends to get all the attention. But as a native New Yorker, I promise the Empire State’s fall foliage is just as gorgeous. The best way to do a New York State fall road trip is to do a big loop, starting and ending in New York City.

Along the way, you should visit the cutest towns along the Hudson River. The best town for hiking and antiquing is Cold Spring. Before heading out on a hike, stop at Hudson Hill’s, famous for its chocolate french toast. 

Another great town is Beacon, where you can find Dia Beacon, a contemporary art museum as good as any in New York City. After the museum, eat at Brother’s Trattoria, a cozy Italian restaurant. If you feel like getting into the Halloween spirit, stop by Tarrytown. The author of The Legend of Sleepy Hollow, Washington Irving, lived here, so the town goes all out with pumpkins, skeletons, and headless horsemen every year. 

Finally, history buffs and foodies shouldn’t skip Poughkeepsie. Tour the home of Franklin Delano Roosevelt and then dine at the Culinary Institute of America, where Anthony Bourdain studied cooking. The Hudson River Valley has something for everyone.

Thanks to Stella from Around The World in 24 Hours for sharing this awesome New York road trip. We have previously taken a day trip from New York City to Bear Mountain , in the heart of the Hudson Valley and can attest that the scenery here is breathtaking.

Finger Lakes, New York

Click here to open Google Maps for details of this road trip around the Finger Lakes in New York

Western New York is especially beautiful in the fall. The weather gives way from hot summers to crisp mornings and evening and temperatures ready for jeans and t-shirts on a warm day or light sweaters in early fall. You can spend just about a week on a road trips to the Finger Lakes with two days in each of these these locations: 1) Corning, 2) Watkins Glen, 3) Chemung County. If you have time, add Hammondsport to your Finger Lakes itinerary.

The Corning Museum of Glass and Rockwell Museum are a must before leaving Corning to explore the beauty of the Finger Lakes region.

Watkins Glen

This is the perfect city in the Finger Lakes for a romantic weekend getaway . Their state park is a must see experience! It’s absolutely stunning and you can take an enjoyable, easy hike there. A sunset sailboat ride with Schooner Excursions around Seneca Lake is a great idea if it’s the right time in the season.

Chemung County

The National Soaring Museum is incredibly interesting and if you visit at the right time, you can take a hang glider ride from the same location in Elmira. This area is also deemed “Mark Twain Country,” where he spent many summers writing and enjoying the area.

He famously wrote The Adventures of Tom Sawyer and The Adventures of Huckleberry Finn at his study, which is available for the public to visit at Elmira College. For those of you that have visited Twain’s boyhood home in Hannibal, Missouri , this will be a perfect place to visit to learn more about his iconic works.

Hammondsport

If you have time be sure to travel the short distance to nearby Hammondsport as well. Dr. Frank’s is a winery that offers tastings and a beautiful view of their vineyards in the area. We recommend taking a seaplane ride with Finger Lakes Seaplanes over Keuka Lake too. It’s especially splendid during fall! 

Thanks to Mikkel from Sometimes Home for sharing a part of New York that we are particularly excited about visiting in the near future.

Road tripping around the New England states offers a little bit of everything, with an eclectic blend of urban beauty mixed in with breathtaking rural bliss. Whether you are intrigued by the myriad of lighthouses along the coastline or perhaps want to learn all about the history of the Salem witches, planning a road trip around northeast USA is always going to offer plenty of opportunities for amazing experiences.

We think the above collection of road trips offers a diverse blend of experiences and we want to thank each and every travel blogger for contributing to this post. We look forward to adding other northeast USA road trips to this post in the future, so please feel free to share your favorite trips in the comments section below.

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I love nature ,the green, waterfalls looks incredible. Great article and lovely photos.

Loved this post! keep it up 🙂

road trip is my weakness, and i can die for any of road trip. This article is very useful, hence last week i just reach north america after 1000 km trip by bike. Your article also inspired me to do again, i am planning for new trip, and very soon i will be start. Your photos are really nice…

wow! lovely images and whole content of your journey.

thank you so much

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New England States: Planning the Perfect Northeast Road trip

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6 states, 6 days, 700 miles, countless memories

It has been a goal of ours to road trip through New England for YEARS! Karen is obsessed with tracking all the states she has visited, and the Northeast seemed like a giant black hole in her progress. Somehow for the past few years, other travel got in the way and our New England plans got delayed. The New England states are Connecticut, Rhode Island, Massachusetts, Maine, New Hampshire and Vermont. Both of us have only visited Massachusetts prior to this road trip. We did quite a bit of planning in order to find the perfect route through the New England states, including the best places to visit in New England and the best FOOD! If you already live on the East coast, we hope this journey planner inspires you to take a New England day trip to one of your beautiful neighboring states.

When the American Lamb Association invited us to Portland, Maine for an event, we knew it was the perfect opportunity for us to plan the ultimate New England road trip! Due to timing, we started south, drove up the coast to make it to Maine, and then ventured West across New Hampshire to Vermont. Our route can be done in either direction. With it being Autumn, it actually might have made more sense to start in Vermont and road trip south to take better advantage of the changing foliage.

Connecticut

We started in Connecticut. Our rationalizations were twofold: Karen needed to check this state off of her list, and Hartford was a larger airport than Rhode Island which made travel cheaper and provided more flexible flight options. We’re sure Connecticut has a lot of offer as a state, but we literally just flew in and headed Southeast for the two-hour drive to Rhode Island.

Rhode Island

After the easy drive from the Hartford airport, we arrived in Westerly, Rhode Island. This is a quiet town with beautiful Nantucket-style homes, gorgeous coastal views, and a relaxing aura. During our stay, we spent time at both the Ocean House and Weekapaug Inn , which are historically charming resorts and only 15 minutes apart. These are partner resorts, meaning you can use the amenities of both properties, which is perfect as each property has a different personality. The Weekapaug Inn is a bit less formal and very cozy with lots of fireplaces. They offer birdwatching, adorable rental bikes, and walking trails. The Ocean House is much more grandiose with fine art adorning the walls and very extravagant suites. They also offer many complimentary activities including cooking demonstrations, a croquet field, and even a putting green in the front of the breathtaking property.

Both properties were elegant with accommodations that range from cozy rooms with claw foot bathtubs to expansive suites with massive verandas, outdoor kitchens, jacuzzi hot tubs, and gourmet kitchens where private chefs can create custom meals for your group. Both resorts also offer free luxury car rentals. Take a Mercedes out from the Ocean House or if you are more of a beemer fan, a BMW for a ride at the Weekapaug Inn.

We met with the food forger who sources all the resort ingredients from farms, forges nearby forests, and hosts guests for private and public cooking culinary demonstrations. Talk about a cool job! He provided us some gourmet cheddar to sample and discussed how the resort’s chefs took sourcing locally and seasonally so seriously. We really wished we had time to join his free Master Sauce class that afternoon!

We dined at the Ocean House for lunch and enjoyed the creamiest New England Clam Chowder. We also noshed on two lobster rolls: hot and cold. Gavin preferred the Connecticut hot lobster roll and Karen liked the cold New England-style lobster roll. Either way, they were the tastiest lobster rolls we’ve ever had!

Dinner at the Weekapaug was a full tour of the menu with wine pairings. Dinner started with their Fall Fashioned while seated in the lounge next to the fireplace: poached local cranberries muddled with whiskey. Highlights of the meal include the best oyster we’ve tasted (it can’t hurt that it was seriously local – from about 15 miles down the road) with a watermelon radish foam. The lamb ravioli was the perfect balance of comfort food without being too heavy. A new menu addition, the scallops over butternut squash risotto was a perfect plate to celebrate autumn.

Westerly, Rhode Island was the perfect place to unplug, relax, and let time slow down. From Rhode Island we ventured towards Cape Cod.

Massachusetts

Next, we headed to Cape Cod. The Cape is technically the entire 65-mile “arm” stretching out from Massachusetts with a number of towns along the way. We decided to stay at the very end of the cape, which was about a three-hour drive. If you choose to stay more inland, you would likely shave 30 minutes or more off of your drive time.

Provincetown is the last town at the tip of Cape Cod. This LGBT-friendly town is warm and social. Historic buildings (some of the oldest in America) are just steps away from the beach where you can experience whale watching or dune buggy tours. Head down Commercial street for cute shops, art galleries, and eateries. We found ourselves stopping into old-time candy shops for saltwater taffy, the new-age Fudge Factory for homemade peanut butter cups (they were pretty dang good!), and their Portuguese Bakery for egg tarts (which were a bit disappointing, but the Portuguese cinnamon bread was delish).

We popped into Strangers and Saints for a craft cocktail and upscale gastropub eats. The decor carried a hip vibe, which was a fun contrast to the vintage feel of the rest of the street. Nosh on their clam dip for a traditional New England treat – note, it can feed a crowd! Additionally, they served up Mediterranean fare like curry octopus and reinvented comfort food like deviled duck eggs.

We stayed at the Crowne Pointe Inn . This inn is recognized by the Historic Hotels of America and is super cozy. The driveways are comprised of tons of pieces of seashells instead of gravel, adding to the charm of the inn. The lobby and most rooms feature a warm fireplace which was perfect for when the night breeze came into Cape Cod. 

Dinner at The Pointe at the Crowne Pointe Inn featured fish and seafood that was pulled right from the bay down the street – talk about fresh!! We loved the lobster gnocchi with an irresistible lobster butter sauce. The halibut came on top of perfectly cooked risotto with a pea puree. The most impressive part of dinner, however, was the massive two-pound whole lobster! 

Traveling from Cape Cod to Portland, Maine was one of the more entertaining driving segments of the whole New England road trip. A few pit stops along the way gave us time to stretch our legs and experience additional aspects of New England history. About an hour from the Cape was Plymouth, MA, home of Plymouth Rock. While the stop was relatively quick (after all, it literally is just a rock, and much smaller than you’d expect) it was a fun part of American history to experience. If you have time, join a tour or visit the neighboring museums. We only hung out for about 10-15 minutes and then continued north.

In no time we were passing Boston. If we had more time we would have totally stopped in Boston for a day or two. Since we had to be in Portland by that evening, we targeted Salem, MA, for our next stop. Salem is only an hour drive north from the pit stop at Plymouth Rock. It just so happened that we were visiting a town known for their famous witch trials on Friday the 13th AND during the month of Halloween! CREEPY! While nothing paranormal happened to us, the town was bustling with lots of people, a street market, and lines outside of haunted houses, torture museums, and fortune tellers. We spent some time wandering through the Salem Witch Trials Memorial . You’ll see an old graveyard as well as Memorial stones for all 20 people who were executed during the months of the Salem Witch Trials.

About one block down from the memorial, we walked to the Notch Brewery for an Oktoberfest beer and a pretzel. It was a really cool spot right on the water. It would have been fun to have stayed the night on such a spooky day, in this spooky town, but we needed to head northbound for another hour and a half drive to Portland, Maine.

Portland, Maine is an adorable town with unique, old architecture and a pretty darn fantastic food scene. Our first dinner was at The Honey Paw and was part of our event with the American Lamb Association . We noshed on craft cocktails and ate Asian-Fusion dishes with an emphasis on lamb. It was spectacular! A few notable dishes were the lamb dumplings, lamb Khao Soi soup (we haven’t had Khao Soi since our journey to Chiang Mai! ), and the lamb Moo Shu. 

Prior to starting our farm adventure, we woke up early to head to The Holy Donut. This spot is voted as one of the top 10 donuts in all of the US. What makes them unique is that they make their donuts with MASHED POTATOES! We’re not sure how they do it, but their donuts are magical. Top picks are the apple, chai and sweet potato donuts.

After stuffing ourselves full of sugar, we hopped on a bus with 20 other food bloggers and journalists from across the country. We took a scenic tour of Maine and pulled up to the North Star Sheep Farm . The farm was picturesque with bright pastures and glowing trees that were changing colors with the season.

We started the morning with a lamb-inspired baaarunch where we noshed on sweet potato lamb hash, lamb sausages, sheep’s milk yogurt parfaits, and even lamb bacon! After stuffing ourselves, we visited with sheep, donkeys, rabbits, and horses as we explored the farm.

Later we were previewed to a full lamb butchery demonstration. Up until this event, our experience with lamb was typically centered around the traditional cuts. Being able to experience the different tastes, based on the cut, was so interesting. They all tasted different! The demonstration really opened our eyes to using new cuts of lamb to cook more adventurous dishes. We were inspired to braise lamb shank and cook it into a ragu as well as make lamb stock for hearty fall stews. We clinked our glasses filled with custom-made cocktails as we savored even more lamb dishes to wrap up our time on the farm.

Later that night we enjoyed small bites and cocktails with the lamb crew at The Press Hotel . The hotel was the perfect location for the blogger event as the entire hotel was themed around journalists. The wallpaper and carpet artistically displayed letters and typography and antique typewriters adorned the walls of the lobby. The rooms were modern and featured a gorgeous shower with floor to ceiling marble tiles.

Even though we technically ate at the hotel, we HAD to visit Eventide Oyster Co for some Maine seafood. This spot came highly recommended from a number of our foodie friends on Instagram . We got a dozen of some of the most delicious oysters in the US, the lobster stew, and the world-famous brown butter lobster roll. Although the lobster roll was relatively small, it seemed to just melt in your mouth. The bread was incredibly soft compared to crusty rolls you find elsewhere, which made this lobster roll extra unique.

The next morning, we went back to The Holy Donut to get our fix and then we hit the road towards New Hampshire and Vermont, the final leg of our New England journey.

New Hampshire

When driving from Maine to Vermont, there were a number of routes to take. Upon looking at the map, we thought that driving into the mountains logically seemed like a prettier drive. We chose right! The first half of the four-hour drive to Stowe, VT was pretty but didn’t have many pit stops. About halfway through, we were in the midst of the White Mountains and were overwhelmed by the Autumn colors. The mountains were orange, almost as if they were afire! We stopped at Crawford Notch State Park on Mount Washington as it had a nice roadside pull off. Gavin played around getting some gorgeous photography. Additionally, not even a mile down the road were a number of roadside waterfalls to see and snap photos.

While we didn’t have time to stay overnight in New Hampshire, we drove through the adorable town of North Conway. We’re sure there is a cute bed & breakfast available for you to rent. We passed the cutest historical train from 1847 chugging down the tracks, as guests looked out the windows at the fabulous fall foliage. You can book your ride through the Conway Scenic Railroad . Another lodging option in New Hampshire is the massive Mount Washington Resort that we passed on our route.

Vermont is the place to go for cozy romance and artisan foods. After driving through the breathtaking White Mountains in New Hampshire, our next pit stop was in Cabot, Vermont. This is only a slight detour from our route and brought us to The Cabot Cheese Factory . We tasted every type of cheese they produced and left with some goodies. Most notably was their Everything Bagel Cheddar, we’re obsessed! Overall, it took maybe took 10 minutes, but if you are interested in a factory tour you could absolutely spend more time there. Note, we found a lot of Cabot cheese being sold in Waterbury, so you can still get their cheddar in gift shops around town if you choose to skip this stop. 

Next up, we stopped at Bragg Farm Sugarhouse . This small sugar farm and gift shop was a peaceful spot to see the old-time equipment used to make and bottle maple syrup. We also tasted their four syrup varieties, picked a favorite (the Amber) and bought a bunch to bring home.

After getting back on the road we wandered to Waterbury. A lively town very close to our resort destination with a number of things to do: 

– Ben and Jerry’s Factory : Be prepared for long lines, then nosh on the famous ice cream overlooking the beautiful Vermont mountains.

– Cold Hollow Cider Mill : Free samples of their apple cider (score!), a peek at the antique equipment, and 75 cent apple cider donuts.

– Smugglers Notch Distillery: For a $3 tasting fee try their award-winning spirits including vodka, gin, whiskey, bourbon, rye, and even a maple rum! 

The city of Stowe was not far away, and that was the location of our lodging, The TopNotch Resort. On the way in, we stopped at Von Trapp Brewery and Bierhall and relaxed while enjoying a flight of their beers and a bratwurst. The Biergarten was large and the grounds had cornhole, picnic tables, and sweeping views.

Finally, we concluded the day’s road trip and arrived at the TopNotch . The resort offers indoor and outdoor pools, relaxing outdoor areas with firepits, a casual bar compete with shuffleboard (The Roost), spa, fitness classes, and an upscale dining restaurant (Flannel).

Our theme of Vermont was “Maple Everything” and that held true while dining at Flannel . We started with a Maple Manhattan cocktail that was so tasty, we ordered it all night. Another memorable dish was their fall pasta. Ribbons of homemade pappardelle, with butternut squash and slathered in a maple sage butter. It was the perfect balance of sweet and savory! Another thing we’ll miss is their smashed fingerlings. They were the side served with our perfectly cooked filet, but we were RAVING about how buttery and delicious they were.

The next morning, we were so relaxed that we decided to zen out even more at the spa. Due to tight timing, we opted to get a quick breakfast at Flannel once again. We continued our infatuation with maple by ordering their eggs Benedict (complete with a maple chive Benedict sauce), maple sausage, and pancakes with (you guessed it) more maple syrup. 

We don’t always make time for the spa when traveling but the TopNotch Resort was so relaxing, we decided this was the perfect place to continue to indulge ourselves. At the spa, we enjoyed services like the maple sugar body scrub, Swedish massage, and a pampering facial. The spa also has a sauna, steam room, and jacuzzi for additional relaxation time, which made our spa time even more valuable.

The resort was so relaxing. We loved cozying up by the fire with a cup of coffee and seeing the beautiful fall foliage from the expansive windows in our room.

We were so sad when it was time for the 45-minute drive into Burlington for our flight home. Burlington has a number of really terrific breweries and cideries. We had every intention of getting to Burlington early enough to hit up a few. In reality, we liked the resort so much, we spent the morning relaxing. We were able to carve out about 40 extra minutes to have a bite and a brew prior to our flight. We chose Zero Gravity Brewery and were not disappointed. Vermont is the perfect romantic getaway to relax and connect with your loved one. 

We found this New England road trip to be incredibly romantic, especially because early to mid-October is the best time for fall foliage in New England. We truly think that this is one of the best road trips in the USA. It is perfect for foodies because of the varying regional specialties across each state, but this is also a great family road trip because the states are so close to each other, which really breaks up the drive. We hope that our road trip planner not only inspires your East coast road trip but potentially a road trip across America!

Be sure to pin this post to save this New England travel itinerary!

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18 comments.

Mary Reinsberg

Great job documenting your travels. I wanna go!

Karen Reinsberg

Thank you! The trip far exceeded our expectations, you need to try and go in Fall of 2018!

Wonder what it’d be like to go in mid April….

It would probably be a bit cooler but hopefully you could catch the spring flowers starting to pop up!

Hi Yin, mid April is not the best time in New England. The only flowers you’d see would be daffodils and forsythia. April is mostly mud season here. It might be nice & spring-like, or you could get a full-on blizzard. Most likely 50s & wet.

Hey Jane – Thanks so much for your insight! April in New England sounds a lot like April in MN, where Karen grew up. 🙂

Josie Lopez

We just both turned 71 and want to do this for our 50th wedding anniversary October 12th…we will be leaving around the 15th…will be flying into Boston….is this feasible for two active seniors who make road trips all the time…meaning driving and weather?…just like Karen, Josie, my wife, has always dreamed of visiting New England in the fall…

Absolutely! When we took this trip, Karen was one month out of ankle surgery and was actually in a wheelchair! The only area that was difficult for us was Cape Cod, as the historic buildings were not always handicap accessible. Additionally, Provincetown had some pretty steep hills. There are 15 cities that make up Cape Cod, so that might not be the case for other cities. The drive is pretty easy and the weather should be beautiful. Happy Anniversary and have a wonderful trip.

Marty Rowland

What an awesome itenerary! My hubby and I are planning a road trip in October. I have been looking at maps. Would you mind telling me what highways you took from Portland all the way to Stowe? I know there are different routes, but yours sounds like the perfect route to see what would interest me. Thanks! Marty

If you use google maps, choose the route that goes through the mountains, near Mt. Washington. It looks like it was I-93 to US-302 E.

Hi, what a wonderful wealth of information, thank you! Driving to a wedding in Brooklyn NY the weekend of July 4th…want to go up the coast through the NE states… feasible this time of year? Any suggestions are most welcome, thank you!

That is totally feasible! We bet New England will be very festive for the holiday.

What are the letters on the map? Are they tied to the places you stayed or visited? I couldn’t find a legend.

Those are the places we visited. We didn’t have a legend as we built the image as a way for people to see the general road trip path. That’s a great recommendation though! We will look to add that as an enhancement in the future. Happy travels. 🙂

Terry Butler

Coming from Columbus Ohio we have four days what would you recommend where to start and what airport to fly into and fly out of , will rent a car at the beginning Mostly wanting to see the coast line thank you

If you’re planning on spending more time on the coast, we’d recommend doing the leg of the trip from Westerly, Rhode Island to Cape Code to Portland, Maine (or vise-versa). Search on the calendar function in Google Flights to see if it is cheaper to start or end in Portland. Since you’re renting a car, consider flying into other nearby airports as well. We flew into Hartford to save a substantial amount on flights. Have a blast!

Where did you stay in Portland ? And how many days should we stay around there , Thank you

Wonderful article! Thank you so much for sharing this information. This is so helpful for me as I start to plan my trip to New England!

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Home » Blog » The ULTIMATE New England Fall Road Trip Itinerary

The ULTIMATE New England Fall Road Trip Itinerary

The Northeast USA is arguably one of the most beautiful places in the entire world during fall. For that reason you NEED to add a New England fall road trip to your bucket list!

Prior to this trip, exploring the northeast had been on my travel radar for the longest time. I am stoked to say that New England definitely lived up to the hype and I am excited to share this New England fall road trip itinerary with you all! (3 day, 5 day and 7 day itineraries)

Read on to find out all the must-see places for fall foliage, where to stay, what to pack, the top hikes to take, photography inspiration, and more! I even provide you with a handy map to use for planning and navigation. In my opinion this is the BEST New England fall road trip and I hope you get the chance to take it!

Disclaimer : This blog post may feature some affiliate links, which means I get a small commission if you make a purchase (at no extra cost to you). It’s one of the ways I can keep producing free guides and resources for my readers. Learn more about my affiliate policy  here . Thank you for the support!

New England Fall Road Trip Itinerary

Before we jump into it, I do want to add a disclaimer that this road trip was my own experience during the 2018 fall season . Every year is different, some more magical, and others less so.

I will do my best to help you plan the perfect New England fall road trip itinerary, but you will need to go in with an open mind! Honestly, some of the best trips I have ever taken have been when things haven’t gone to plan. Sometimes all the planning in the world cannot change the weather!

Okay, let’s jump into how to plan a fall New England road trip !

How to plan a New England fall road trip

There are generally two ways to approach planning for a New England fall road trip. The first is to meticulously plan everything in the attempt to not waste a moment, and the second (the option we went with) is to pretty much not plan at all. Sounds weird right? Why would you not plan and wouldn’t that potentially waste you time and money? Well, at this time of the year, it kind of works in the opposite way.

The reason for this is that fall colors gradually change from green, to yellow (or orange, red, purple) until they fall off. Not all trees in an area change at the exact same time. There’s a point in the fall transition where most trees are changed to their beautiful shades of yellow, orange or red prior to falling off and with minimal green trees. This is considered “peak fall foliage” or “peak fall color”.

Peak color doesn’t happen at the exact same time every year (usually varying a week or so either way). It can vary due to a variety of factors but this is mostly due to weather. By not booking hotels or camping prior to your Northeast fall road trip, this allows you to be flexible. You can go to the areas that are at “peak color” rather than spend time in a spot that isn’t yet fully changed or worse, the leaves have fallen.

When to start planning your New England fall road trip itinerary

Advantages and disadvantages come with this method of not planning. The major advantage of not booking all your accommodation in advance is flexibility . You won’t miss the colors because they happened to be a week late or earlier than expected. You can drive to wherever the colors happen to be best in that moment.

This comes with a downside though… accommodation prices and availability. Fall is extremely busy in this part of the country . Like you, many others choose to take East Coast fall road trips in the hope of seeing the incredible beauty that comes with the changing of seasons. This means hotels and vacation rentals can book out well in advance, leaving the remaining last-minute bookings quite expensive.

We ended up opting to mostly find accommodation as we went along, including some last-minute vacation rentals and hotels /motels. We tried to stay at a budget of around $80-150 USD per night, which did narrow down our search a little but overall the places were more than adequate, use Expedia to get price comparisons across multiple booking sites and save you time searching for a place to stay. A couple of times we did have to drive to places slightly further out of town to find a more affordable price but this was an okay compromise to have the extra flexibility.

If you need to rent a car, check out Kayak for price comparisons from rental agents. Or you could use this road trip to test out van life! Rent an RV or camper from Outdoorsy , and you won’t have to worry much about accommodations.

Another option is to bring camping gear .

Keep in mind though, at this time of the year some of the campgrounds are beginning to close. Some places we traveled through didn’t seem to have many tent camping options. In saying that, there was the possibility of sleeping in your car. I have a guide all about sleeping in your car on road trips – check it out!

If you are thinking of camping, you can check sites in the area on The Dyrt where you can see which are open and the facilities available as well as reviews from previous campers. Click here , or use my code reneeroaming for a free 30 day trial .

With all that being said, how you want to plan your Northeast fall road trip is up to you. Do you want to take the chance of potentially missing the peak colors and pre-book more affordable/convenient accommodation? Or do you want to pay slightly more for accommodation and make sure you are seeing the best of the colors? It’s up to you. Either way, we found this be the most accurate and up-to-date map of where the colors are peaking .

Mid-October is often the best time to take a New England road trip for leaf peepers, but it’s helpful if you can be flexible with your date. For reference, we took our fall New England road trip on October 8 – 12, 2018 . But don’t take those dates as a sure thing because peak color can change year to year! Just remember to pack your camera to capture those autumnal colors. You can see the equipment I use further down in the post.

Best New England fall road trip itinerary

Below I’m sharing a suggested itinerary for your New England fall road trip, based on our own adventure. First off, here is a map with all the best spots linked and pins for each day of the itinerary, see below.

Now let’s talk through the day-to-day itinerary…

Day 1 – Dixville Notch State Park

Fly into Boston , Massachusetts and pick up a rental car . From here, drive 4 hours north to Dixville Notch to begin your New England fall road trip. Dixville Notch is a very small area, but for what it lacks in size it makes up for in beauty!

The main road that travels over Dixville Notch initially winds its way past some cute farmland surrounded by rolling hills. The drive then passes stunning Lake Gloriette , up over Dixville Notch and down the other side of the pass-through incredible fall foliage to a couple of serene picnic areas and walks.

Plan to do the stunning Table Rock trail which is a short one at only 1.5 miles round-trip, but a relatively steep 700 feet climb. This gives you epic 360-degree views over Dixville Notch from above, and the photos are beautiful! If you have timed it right, you might even be able to enjoy sunset from up there.

Unfortunately when we were there, the clouds were low and covering the views.

Instead, we parked at what is labeled Whittemore Family Cemetery on GoogleMaps and hiked a short trail that leaves from the parking lot. This is a great alternative if the weather is not cooperating.

This trail made its way through a vibrant forest that leads to a cute little bridge and stream. The hike would only take 10-15 minutes round-trip without stopping. It was a great way to stretch the legs and take a moment to snap some photos of our first glimpse of fall colors.

After finishing your hike at Table Rock, or the alternative trail, head back to nearby Colebrook for dinner and a good night’s rest in your hotel . You can also book into this great cottage on a farm or Tentrr’s Signature Site for luxury glamping.

Day 2 – Stowe

Wake up early, grab some breakfast at Mostly Muffins in Colebrook (so yummy!) and then drive west towards Stowe , Vermont. On the way, you will pass loads of beautiful fall foliage and small rural towns including the memorable Island Pond. The Great Vermont Corn Maze is also a fun stop if you’re into that sort of thing.

After a beautiful drive to Stowe, you can spend the rest of the day exploring its charm, cute gift stores, and scenic walks. We had lunch at the Green Goddess Cafe and it was amazing! We then took a quick walk along the bike path which leaves from behind the Stowe Community Church and runs along the river. You can also take a brewery tour in Stowe to sample locally made beer, spirits and ciders.

From this vantage, there are some great views of the church worth photographing. Finish the night off with a delicious pizza at Piecasso in town – we definitely recommend this restaurant! Stay the night in Stowe at The Green Mountain Inn or in The Loft at Hobble Inn .

Day 3 – Smugglers Notch & White Mountains

Day 3 of your Northwest fall road trip will be a busy one! Wake up early and head to Smugglers Notch . This area has a road that goes up and through a small gap between two mountains (referred to as a “notch”). It is quite similar to Dixville Notch, but in my opinion, Smugglers is even more spectacular.

This was one of the spots we were most looking forward to on our New England fall road trip, and it didn’t disappoint! The mountains on either side are HUGE, and there are so many beautiful twists and turns in the road to photograph and check out.

Definitely drive this to the other side and back before moving on to your next location. Another option is taking the Gondola SkyRide at the Stowe Mountain Resort, for beautiful aerial mountain views.

From Smuggler’s Notch, drive south to Pomfret, Vermont .

Taking Cloudland Road south from Pomfret to Woodstock will take you along cute dirt roads lined with fall colors, rolling hills, and quaint farms. A necessary stop along this route is the farm located opposite “Elm Grove Farm” on GoogleMaps, often referred to as “Sleepy Hollow Farm” . It’s a great little photography stop that captures one of the most photogenic farm properties you will ever see.

Sugarbush Farm is another local property you can visit, though we didn’t go there ourselves. I hear their maple syrup is delicious!

Now, time to head back to New Hampshire! Your scenic drive today will take you through Franconia Notch State Park. At the base of the White Mountains, the town of  Lincoln is a good place to end day 3 of your New England fall road trip. Stay at Woodwards White Mountain Resort or the Loon Mountain Apartment .

Day 4 – White Mountains

Your New England fall road trip would not be complete without a drive along the famous Kancamagus Highway . Leaving early on day 4 from Lincoln, there are a lot of epic road-side views on this stretch of road. A number of pull-outs also allow for some great photo opportunities. Continue east until you hit the Rocky Gorge Parking Lot. Here you can take a walk along the beautiful Swift River and get views of the beautiful Falls Pond . North Conway is a cute town on the east end of the Kancamagus Highway, and a great spot for lunch or a stroll around town.

From Rocky Gorge, we backtracked a short distance to drive up  Bear Notch Road . Bear Notch provides a scenic drive along a mountainside and more roadside pullouts for some gorgeous photo opportunities.

At the end of Bear Notch Road, drive north to Crawford Notch State Park . Here, you can explore the backroads and snap photos of all the beautiful fall colors. A side-trip option in this area is a hike up the Mount Willard trail . It’s a relatively steep, but short 3.2-mile round-trip hike to a clifftop overlooking Crawford Notch. The views from there are unreal! Again, unfortunately, the weather wasn’t cooperating so we had to skip this one.

Next, continue north where you have the option of taking a short detour to the Mt Washington Cog Railway . Here, you can catch an old-school train up to the summit of Mount Washington, the tallest mountain in the northeastern US at 6,289 feet. Due to the bad weather, we kept driving, but if you are a fan of trains then this should not be missed!

To end your day, depending on availability you can stay in the nearby towns of Carroll, Franconia, Littleton, or Bethlehem.

We stayed in Franconia ourselves and chose to drive to Bethlehem to have dinner at the Cold Mountain Cafe . It if works out with timing, we highly recommend it as a delicious way to end a busy day.

There are great hotels to chose from, the Hampton Inn in Littleton and Stonybrook Motel & Lodge in Franconia are lovely options or you can opt for vacation rentals. On the Mountain Suite in Carroll, Rustic Log Cabin in Sugar Hill and Kilburn Place in Littleton are worth checking into.

Day 5 – White Mountains

Day 5 is the last day of your New England fall road trip, and what better way to start than with a sunrise hike up to Artist’s Bluff . This is a short 1.4-mile walk up to a stunning hilltop that overlooks Echo Lake , and the fall foliage here is insane! Unfortunately, it was raining when we drove past here (a common theme on our trip!) so we opted to skip the hike as the clouds were hiding most of the views.

We continued on to Flume Gorge which is a relatively easy 2-mile loop hike and one of our favorite stops of the trip. Multiple waterfalls, streams, and covered bridges keep the eyes entertained for the whole 2 miles. Do note that there is a $18 per person entry fee (I definitely recommend making advance reservations) but we felt it was very much worth it. In fact, we spent a couple of hours exploring this area and even in the rain it was absolutely gorgeous!

By now your Northeast fall road trip is coming to an end. It’s probably time to head back towards Boston to catch your flight… or onward to your next destination (see more below!)

7 day East Coast fall road trip

If you really want to take an incredible Northeast fall road trip and have some extra days ( 1 week total ), here is what I would recommend. Add a couple of days in between Stowe/Smuggler’s Notch and the White Mountains. It would be fun to spend a day in Burlington and walk along Lake Champlain, or check out Waterbury, Vermont. With these extra days, you can drive further into Upstate New York and the Adirondack Mountains , where the colors were absolutely incredible. There are also abundant hiking opportunities, and the beautiful town of Lake Placid to explore. Lake Placid has some amazing accommodation options and beautiful views so it is definitely worth spending a night there. Try the Crowne Plaza or this Rustic Room or search cabins in the area for larger groups.

As an alternative to the Adirondacks, you could scoot over to Maine and visit Bar Harbor and Acadia National Park . Acadia has some really unique scenery, boasting both coastal views and mountain tops! Bar Harbor has plenty of great vacation rentals available.

Check out my blog, How To Prepare for Hiking Trips , ahead of time to prepare!

As I know many of you will ask, we opted to take a sunset hike in the Adirondacks (see photo above), however I have been asked by locals to please not share the exact location. There are some concerns about the potential damage of increased trail traffic and it was pointed out to us that parking spots are also very limited.

I urge you to be responsible and always abide by Leave No Trace Principles when exploring the outdoors. You can read my blog, Hiking Trail Etiquette Rules You Should Know , to learn more and click here to read my in-depth guide on How To Follow Leave No Trace Principles.

3 day New England Road Trip

You could do this New England fall road trip in 3 days with some adventurous spirit! It would be kind of rushed, and you wouldn’t always be able to be in the best spots for sunrise or sunset. That being said, if it’s all you have, go for it! It’s definitely doable and would also be a blast. I hope you don’t mind missing out on some sleep though 😉

Some options to put together a shorter Northeast fall road trip itinerary would be to cut out the Pomfret / Sleepy Hollow Farm section, as that does add some driving hours. Another way to cut downtime would be to combine your visit to Stowe and Smuggler’s Notch into one day.

New England fall road trip packing guide

There are some essential items you should pack for your Northeast fall road trip to make it as enjoyable as possible! I hadn’t explored much of New England or Upstate New York before this trip and found the weather to be a little up and down. In fact, one minute it was sunny and the next freezing and rainy! You’ll definitely want to pack some additional layers for your leaf peeping adventures.

This packing guide is also tailored towards people who enjoy hiking. If you don’t plan to hit the trails, simply leave off the hiking-specific items when using the guide. For those choosing to camp, I have an entire guide and packing list for car camping essentials , so make sure to check that out!

Insulated jacket

Mid-layer :.

Perfect for chilly mornings and evenings. Opt for something lightweight like a fleece or pullover. Recommended mid-layer .

Insulated jacket :

It’s likely to get colder than you are expecting, especially if you plan to be out during sunrise and sunset hours. In fact, it even snowed in New Hampshire towards the end of our trip! So I would highly recommend packing a puffy jacket or a parka that has insulation. Recommended insulated jacket .

Rain jacket :

Do not attempt to take a Northeast fall road trip without a rain jacket/coat ! It rained at least once every day we were on the East Coast. Although it didn’t ruin our trip, it could have if we didn’t have adequate rain protection. Recommended rain jacket , recommended windbreaker .

Casual clothes :

Pack some casual and/or nicer outfits if you plan to eat out at restaurants. This is of course optional though! Check out my Favorites page on Backcountry for some recommendations.

Hiking shoes:

I was VERY happy that I packed waterproof boots for our East Coast fall adventure! We experienced wet, muddy, and cold conditions and waterproof boots made a huge difference. I suggest choosing a pair that can be worn both casually and also when hiking. If you prefer a more solid, supportive hiking boot the Columbia Newton Ridge Plus Waterproof Hiking Boots are a great choice. We also have a guide on all the best hiking shoes , so don’t forget to check that out when shopping for new hiking boots!

Merino wool socks :

Wool socks are the best for preventing blisters and also letting your feet breathe. Recommended hiking socks .

Hiking pants & Leggings:

Don’t stress too much about bottom layers, just make sure they are comfortable and practical for road tripping. I personally like wearing leggings, jeggings, or comfy jeans on road trips, as then I can transition from car, to around town, to hiking, and more. Choose whatever feels comfortable and practical for you! Recommended hiking pants ; hiking shorts ; hiking skort , hiking dress , hiking leggings .

Beanie & Gloves:

As I mentioned above, it even snowed during our New England fall road trip! I would highly suggest packing a beanie and some warm gloves .

Day pack/hiking backpack :

Choose something with hip and chest straps for optimal comfort and practicality. Recommended backpack . When taking short walks or exploring roadside stops I often prefer to opt for a small hip pack instead of a backpack. Just something to fit my phone, lip balm , sunglasses , and any other essentials.

Navigation :

When driving, have Google Maps or Maps.Me handy. We often lost phone service when driving in the mountains of New England and down back roads. For hiking, carry a physical map and a compass , and download offline maps onto your phone. I use Gaia GPS – click here to get 20% off a Premium membership!

Camera + batteries :

Optional but trust me, you will want a camera to capture the incredible fall foliage! Check out the camera gear I use to capture my travel photos and the camera bag I pack it all in!

Every road trip requires snacks! We found it challenging to find food between towns and also after hours. Bring whatever your favorite snacks like nuts, seeds, granola bars, dried fruit, etc. My go-to snacks . If you enjoy drinking coffee then it’s best to bring along a reusable mug or tumbler. Recommended mug ; insulated tumbler . Having your own travel utensils / cutlery is a great way to cut down on single-use plastics when ordering take-out food.

Road trip playlist + Podcasts:

Don’t forget to download some good tunes and podcasts for your road trip. For music, check out my playlists on Spotify . For podcasts, we have an entire guide on the best road trip podcasts !

Want more packing & gear tips?  Check out our guides on what to wear hiking , car camping gear essentials , how to plan a national parks trip , and the best hiking shoes .

I hope that helps you plan an incredible New England fall road trip! With a little flexibility you’re guaranteed to have an epic road trip, even if the weather doesn’t cooperate the whole time. Have an amazing time and feel free to leave a comment and let me know how you got on 😊

PIN for later planning!

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26 comments

Greetings!What are your suggestions for including Salem MA in a 5 day trip? Thank you so much!

• Pingback: New England Fall Road Trip Itinerary - 4 days in New Hampshire & Vermont - Laura Peruchi | NYC

HELLO! Thank you for posting the perfect Fall road trip. I would love to take your advice and incorporate and extra two days to go up into the Adirondacks. Can you please suggest the best place to go and things to do with that two days? I need to book ASAP because we are going the last week of this September. If you could please get back to me quickly, it would be most appreciated. We are from Florida and know nothing of the area, so any advice would be very helpful. Thank you so much. Sincerely, Chris in Florida

• Pingback: 60 Fabulous Fall Aesthetic Photos » Lady Decluttered

Your blog is packed full of helpful information and absolutely beautiful photos!

I was curious if you could recommend an itinerary that would also include Niagara Falls?

I love your photos! Do you offer tours? Thanks!

Hi Renee, Love this post! My fiancee and I are planning our honeymoon to the Adirondacks this fall, so I loved your suggestions and your photographs are beautiful! I was wondering if you knew where you got the grey hoodie you’re wearing in several of your pictures? It’s so cute and looks prefect for fall day hikes.

Hi! Thanks for the wonderful info! We’re just starting to plan a trip for next year. Question, is there nothing to see on the four hour drive from Boston to Dixville Notch? Again, we’re just starting on this, but it appears you’re going up the same way you’re coming back? Thank you so much for the help and this awesome site! 🙂

Gorgeous photos! I’ve spent time in New England in the fall its incredibly idyllic. (Lived in Maine and Massachusetts for 3 years) The White Mountains is truly one of God’s masterpieces. Excellent post!

Hey there!!! As far as the smugglers notch and Stowe area… is it redundant to do the gondola ride as well as take the drive up smugglers notch? Should we pick one or the other? Thanks!

• Pingback: New England Fall Road Trip: The ULTIMATE Leaf Peeping Itinerary - Renee Roaming - Fitness Sport und Gesundheit

Thank you for the Google Maps — so helpful!

Planning a trip for this October, but we have only 3 days! Trying to decide how to see the most of everything! lol any recommendations for “must sees” for only 3 days!?

I can’t wait to travel to the east coast this fall! (I live in California, and we don’t get much of a fall here). Thanks for sharing your itinerary, I’m planning on a road trip and didn’t know where to start! I was wondering where the second picture was taken? (Of you and the water in the background) Thanks!

Did you find out where that 2nd photo was taken? I also would like to go there this October.

I would like to know the shooting spot of the second photo (Stowe?)

This blog post is just amazing and the pictures so beautiful ! Thank you for sharing your experience. I love travelling and was looking for new ideas, this is definitely one 🙂

Wow, these fall colors looks awesome! Thank’s for this helpful post, Renee!

Thank you for reading Laura!

Thanks for sharing your stunning pictures! I totally agree with what you said about not planning in order to find the best colors. The fall we spent living in Upstate NY and hiking all over the NE contained many of my favorite days of my life so far, there truly isn’t a bad hike when it’s that colorful! It makes up for the 6 months of winter that follows. 🙂

What a magical time that must have been!

Thankyou for all this indepth info Renee. Should be super helpful when I plan my own fall trip. And of course stunning photos that I really enjoyed.

Thank you!!

Wow, the nature there looks amazing. And your Photos are loveley. Thank you both for this blogpost. Maybe, we can travel there one day. My wife and I live in the North of Germany. Last weekend we took our own Fall Roadtrip in the Harz National Park. The first blogpost of this trip is now online. It’s about the lovely oldtown in Quedlinburg 😉 best wishes Christian

Thanks Christian! That sounds like an amazing road trip, I’ll add it to my bucket list 😉

i’d love to see Christian’s blogpost about Quedlinburg (a UNESCO World Heritage Site). I was there last year and it was wonderful. My grandparents live in the Harz Mountains, Please share a link, Christian.

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US Road Trips: The Northeast

The quintessential city escape: seaside retreats, rolling hills, secluded lakes, beachy hangouts, sunset beers. Pack up and hit the highway with this list of weekend road trip destinations in the northeast United States. Are we there yet?

Jump to: Connecticut | Maine | Maryland | Massachusetts | New York | Rhode Island | Vermont

CONNECTICUT

Photo courtesy of Privet House.

Head to Southport/Westport

If you're in the mood for low-key antiquing and the beach. The Delmar Hotel and Artisan restaurant are around the corner from what is, quite possibly, the sweetest, tiniest town. Terrain , Anthropologie's stunning offshoot (greenhouse, garden center, cafe), has a packed summer lineup of classes and events. Route to take: Straight shot on I-95, 90 minutes from Manhattan. Good to know: The Gray Goose Cafe is adorable for lunch.

Head to Greenwich

If you're in the mood for fresh air and fancy shopping. Hit "The Ave" for boutiques like Privet House . Enjoy a leisurely lunch at local favorite Meli Melo , where specialties include French onion soup and freshly squeezed OJ. If you're still around for dinner, stroll down to L'Escale for harborside dining and specialty cocktails named for the seven heavenly virtues. Route to take: One hour by car from New York City via I-95. Good to know: The Drawing Room serves hand-blended teas and delicious scones with clotted cream. Their adjacent shop is the place to buy decorative pillows and scented candles. Stop off in Port Chester for a pizza margarita at Mario Batali's Tarry Lodge and freshly baked bread and cured meats from the market .

Head to Washington

If you’re in the mood for a classic, picturesque New England town. Dine by the open hearth fire at the Mayflower Inn , pick up hot cross buns and Irish soda bread from The Pantry , or take a picnic and hike the beautiful trails along the Shepaug River in Steep Rock Reserve . Route to take: A two-hour jaunt from NYC. Good to know: Averill Farm has been family-run since 1746. Go in the fall for apple picking, homemade pies, and old-fashioned farm fun. Read more on Fathom: New England Classic: A Design Duo's Favorites in Washington Connecticut

Photo courtesy of White Barn Inn.

Head to Acadia National Park

If you’re in the mood for coastal scenery at its finest. Bike the national park's 45 miles of carriage roads, hike the diverse terrain, and watch the sunrise from atop Cadillac Mountain. Stay at charming and kitsch-free West Street Hotel in Bar Harbor and get popovers fresh from the oven at  Jordan Pond House before gorging yourself on lobster rolls and ice cream. Route to take: Stop along the park’s 27-mile scenic route at Sand Beach, Thunder Hole, Jordan Pond, and Cadillac Mountain. Good to know: For late night bites and weekly karaoke, head to Little A's Sports Bar . Read more on Fathom: Finding Arcadia in Acadia

Head to Rockland

If you're in the mood for farm-fresh food without the Boston or New York price tag. Make a reservation at Primo and enjoy a creative menu that uses produce and animals raised on the property. Route to take: Route 1 affords beautiful coastal scenery, complete with waves crashing into rocky cliffsides and charming lighthouses. Good to know: The Farnsworth Art Museum is also located in Rockland, giving you a good dose of culture along with a fantastic meal.

Head Down the Coast of Maine

If you're in the mood for by-the-book prep, nature adventures, and rural farm areas. Route to take: Skip around from Camden to Rockport to Kennebunkport to Norway. Good to know: Stay at the Country Inn or The White Barn Inn ; stock up on L.L. Bean ; let Ducktrap Kayak handle your paddling details. Read more on Fathom: Little Black Book for Coastal Maine

Photo courtesy of Inn at Perry Cabin.

Head to the Chesapeake Coast

If you're in the mood for a nautical state of mind. Start by gazing at the sailboats from your bedroom window at Inn at Perry Cabin . Get dirty with buckets of peel-and-eat shrimp poured onto tables covered in brown paper by day; clean up for the five-course dinner menu from a Per Se alum at Bartlett Pear Inn . Route to take: Route 301 is a pleasant alternative to the NJ Turnpike and I-95. Good to know: The NYT has a list of finger-licking crab shacks that's worth a gander.

MASSACHUSETTS

Photo by Todd Beeby.

Head to the Berkshires

If you're in the mood for dance, theater, yoga, Shakespeare, and skinny dipping with mountain as the backdrop. Route to take: Saw Mill from NYC; Mohawk Trail into North Adams from Boston. Good to know: Jacob's Pillow , Mass MoCA , Kripalu , and Canyon Ranch are all here. Read more on Fathom: Berkshires Hot List and Breathing Lessons in the Berkshires

Head to Nantucket

If you're in the mood for a new flavor profile on one the coast's most historic islands. Do Provisions for brunch, Ventuno for dinner, and Brotherhood of Thieves for a sunset beer. Shack up at White Elephant or Wauwinet . Route to take: JetBlue flies to the island during summer months. Good to know: Take the pooch. There's a lot of outdoor living, dog-friendly hotels, and off-leash beaches.

Photo courtesy of The Arnold.

Head to Barryville

If you're in the mood for locavore eating, sustainable shopping, patronizing family businesses. Stay at Hillside Schoolhouse , a two-bedroom charmer nestled in the woods of Sullivan County. Head to Benji & Jake's for cold beers and wood-fired pizza on the upstairs deck overlooking Kauneonga Lake. Pick up locally sourced pantry items from modern general store River Market or the Barryville Farmers Market (on Saturdays during the summer). Rent an inner tube and take a ride along Skinner's Falls. Follow with a long and lazy dinner at The Heron . Route to take: Route 97 through Barryville has crazy winding roads, scenic overlooks along the Delaware River, and habitats for birds of prey (once a dirt road referred to as the Hawk's Nest). Good to know: Take a cue from owner Bronson Bigelow, who quit his corporate job to open the inn and make all the furniture in it. Or just shop his collection of upcycled antiques, vintage industrial objects, and restored ice boxes.

Head to Hudson

If you're in the mood for juxtaposing well-worn Victorian charm with big city comforts and a bit of edginess. Stay at Inn at Hudson , drink a perfectly pulled espresso at Swallow , check out the mini food truck emporium on Warren Street, have killer (local, sustainable, homemade) burger with the works at the retro-fitted '50s diner Grazin' , and finish off with a nightcap and live show at Helsinki . Route to take: Ride Amtrak right into town; zip up from NYC in a car on 87. Good to know: Check the schedule for happenings at the cathedral-like Basilica Hudson , an old glue factory that's been turned into a performing arts space. Read more on Fathom: The Best of City and Country Rolled Into One Little Weekend in Hudson, New York

Head to Ithaca

If you're in the mood for a healthy dose of counter-culturalism and hippie goodness. The Argos Inn , a LEED-certified 10-room inn meticulously renovated with heated stone slab floors, velvet drapes, and turn-of-the-century Bergere chairs. It's a ten-minute walk from your velvet-flocked suite to the iconic Moosewood restaurant, which turned all-natural cooking and '70s-era co-operative business ideals into a full-fledge vegetarian kitchen collective. Obviously, pick up a cookbook . Morning coffees can and should be had at the original Gimme! Coffee (now a Brooklyn mainstay). Besides swimming holes and architectural tours of nearby Cornell campus (I.M. Pei! Koolhaus! Richard Meier!), you're spitting distance from the Finger Lakes wine country . Route to take: Make it scenic and curve up the Catskill Mountains. Make a sweet rest stop for a few scoops of ice cream made from Cornell's own dairy farm . Read more on Fathom: This Is Where Locavore Was Born

Head to Livingston Manor

If you're in the mood for a monastic environment. Book a weekend at Dai Bosatsu Zendo , a Japanese Buddhist sanctuary where you can workshop the basics of being — like breathing and being quiet. Route to take: The Palisades (from NYC) are soothing and scenic. Good to know: No prior Zen practice necessary. And if you want your alone time with somebody, you can rent a small cottage on the premises.

Head to Montauk

If you're in the mood for an easy, breezy beach weekend. Ruschmeyer's has a retro camp vibe, but the best way to hang is by renting a little something you can call home. Route to take: Drive very early in the morning or very late at night on 495 to Sunrise Highway to the very end of Montauk Highway (avoid traffic by using GPS to navigate back roads). Good to know: BYOB seafood shack Duryea's Lobster Deck and Fishbar on the Lake are musts. Read more on Fathom: Hamptons Guide and Montauk Master Plan

Head to the North Fork

If you're in the mood for large plots of farmland, farmstands, U-picks, and wineries. Book at slow-food hang North Fork Table and Inn . Route to take: Tiny town centers dot the Main Road (Route 25) and Sound Avenue (Route 48). Good to know: The Custer Observatory is open every Saturday from dusk to midnight for stargazing. While in the area: see our North Fork hit list .

Head to Phoenicia

If you're in the mood for agritourism with a Dutch design bent. Try Stony Creek Farm in Walton, where fancy tents with wood-burning stoves are nestled on a working farm. Nightly harvests become dinner. Route to take: Take 87 and stop in for a tour of Tuthilltown Spirits , the distillery where Hudson Baby Bourbon is made. Good to know: The culinary cognoscenti of NYC get their prime cuts from Fleisher's Meats ; you can pick up breakfast sausages at their full-service butcher shop. Read more on Fathom: Catskills Hit List

Head to Shandelee

If you're in the mood for hiking, biking, foraging, and dozing off in the sun. The Arnold House , an adorably Instagrammable 10-room inn (Sferra linens, Pendelton blankets, cork floors), is the perfect setting for your country retreat. Being the proper hosts that they are, the Foster family proprietors offer plenty of fun activities (ice fishing in the winter, ramp foraging in the spring, ravioli making at nearby Northern Farmhouse Pasta ). Route to take: Wind through the Palisades and continue northwest from NYC. Good to know: If you didn't bring your own pooch (the hotel provides dog beds, water bowls, housemade treats), spend some time cuddling with Adelaide, the English Bulldog.

Head to West Kill

If you're in the mood for the simple Catskill pleasures. Star at the Spruceton Inn , a Catskills "bed & bar" with mountain views. Get your pancakes stacked at Phoenicia Diner . Work off the carbs with a picturesque hike to Diamond Notch Falls , a serious hike up Overlook Mountain , or, come winter, some ski tubing on Plattekill Mountain . Dine on savory pies at Table on Ten . Ride Icelandic horses on quiet trails. Or, back at the inn, just play some bocce and make some snacks in your own kitchenette or on the grill. Route to take: Hit the Palisades and roll through Woodstock. No wheels? Coordinate a pick-up with your guest house after catching the Trailways bus from Port Authority. Good to know: Leave plenty of time to get home so that you can stop for antiques and farmstand souvenirs: raw milk and gouda from Byebrook Farm ; old thingamabobs from Lyon Mountain Blue Barn Antiques ; farmy furniture at Wood Bull antiques ; honey and grass-fed meats from Stone & Thistle . Read more on Fathom: Where to Go from NYC, the Catskills Checklist

Head to Lake Placid

If you’re in the mood for adult summer camp in the Adirondacks. Check out Wild Walk, the “High Line of the Forest,” a museum experience suspended in the treetops of Tupper Lake. Canoe or kayak down the Raquette River, and end the day with a good meal and a better cocktail at Liquids and Solids . Route to take: Hit the Taconic Parkway from New York City. Good to know: Stay at Whiteface Lodge for a well-appointed resort experience, or camp near Lake Placid , Saranac Lake , or Tupper Lake for a real back-to-nature experience. Read more on Fathom: A Walk in the Woods Above NY’s Adirondacks

RHODE ISLAND

Photo courtesy of The Ocean House.

Head to Watch Hill/Weekapaug

If you're in the mood for a gorgeous beach escape with excellent cuisine to match. The recently revamped Weekapaug Inn where sail boats, fishing gear, and a discreet, black-bottomed pool are all at your disposal. A meal of locally caught lobster, Matunuck oysters, and native beets is as memorable as the sunsets overlooking bucolic Quonochontaug Pond. Route to take: Head south on the I-95. On the way back to civilization, stock up on freshly baked chocolate chunk and molasses cookies at gourmet emporium The Cooked Goose . Good to know: Killer Swedish massages at Relais & Chateaux sister property The Ocean House are a Zen bonus. Read more on Fathom: Summer with the Kids in Watch Hill

Photo courtesy of Woodstock Inn.

Head to Woodstock

If you're in the mood for quintessential Americana combined with a new, LEED-certified spa. Book the grand Woodstock Inn in New England's most picture-postcard-perfect town. They have a serene spa and delicious farm-to-table cuisine in its casual Red Rooster restaurant. Head across the quaint village green outside your front door and make stops at the old-school Gillingham's general store and Yankee Bookshop before a lovely dinner-a-deux at The Prince and The Pauper , a town institution. Route to take: The Taconic Parkway from NYC. It might be a slightly longer route, but the scenery — and a stop at the old-school Millbrook Diner (3266 Franklin Ave.; +1-845-677-5319) — makes it worth it. Good to know: Do not skip town without a stop for black raspberry ice cream cones at the White Cottage Snack Bar . Open only in summer, this low-key spot is worth a serious, deep-fried detour.

Head to Burlington

If you’re in the mood for getting back in touch with nature and ending the day with a fantastic craft beer. Stay at eco-friendly Hotel Vermont  and dine next door at Chef Eric Warnstedt’s revered restaurant Hen of the Wood . Do some boutique shopping on Church Street, or head down the hill to Lake Champlain for lakeside activites in the summer and winter. Route to take: On your way into the city, stop at Shelburne Farms , a nonprofit farm focused on sustainability education, for tours of their historic barns, tons of scenic walking trails, and classic Vermont foodstuffs from the farm store. Good to know: August First Bakery may not allow laptops, but they have the best bread downtown. Read more on Fathom: It’s All Small Town Good Vibes in Burlington, Vermont

MORE FATHOM-APPROVED GETAWAYS

Have you seen our list of the Most Romantic Hotels in The Northeast ?

Special thanks to contributors Devorah Klein Lev-Tov, Christina Ohly, and Ilaria Urbinati.

We make every effort to ensure the information in our articles is accurate at the time of publication. But the world moves fast, and even we double-check important details before hitting the road.

New England Wanderlust

Connecticut , Maine , Massachusetts , New Hampshire , New York , Rhode Island , Vermont  ·  March 30, 2022

34 Awesome Road Trips From Boston & Best Itineraries (2024)

Boston is an amazing starting point for adventures all over New England and the Northeast. With so many options to visit tons of nearby coastal towns, exciting cities and plenty of quaint, charming villages, there are endless possibilities for road trips from Boston. And since I’ve been road-tripping and traveling all over the Northeast for over 10 years now, I know all the destinations that are worth your time.

This list includes destinations that are all individually under 6 hours from Boston, and if you’re looking for road trip itineraries that combine destinations from this list, be sure to scroll to the end for suggested itineraries to make the most of your road trip!

New England Wanderlust contains affiliate links, and is a member of the Amazon Services LLC Associates Program. We may earn a commission from any purchases you choose to make from our links, at no additional cost to you. For more information, please refer to our  Privacy Policy .

🚙 Need to rent a car for your epic road trip? I’ve got you covered! Click here to check the best prices on Discover Cars!

Best Road Trips From Boston

For this list, I’ve broken down the destinations into four categories: Coastal, City, Charming Towns and Luxury Getaways. For each destination, I’ve also included the time it takes to get there from Boston, highlights of the best things to do, what to expect once there, and nearby things to do.

Coastal Road Trip Destinations From Boston

1. plymouth, ma.

Distance From Boston: 40-50 minutes

If you’re looking for a quick, easy getaway from city life in Boston, a little road trip to Plymouth is a fun way to do that. While the town is known for its history dating back to the early 1600s, they are also lots of outdoor activities, parks and beaches, and combine that with a small-town feel, Plymouth makes for a lovely little escape from Boston.

Best things to do in Plymouth:

• Plimoth Patuxet Museum is a living replica of the original pilgrim colony settlement. If you’re a history buff, this is a must-see. You can even climb aboard the Mayflower II, an exact replica of the ship that brought the pilgrims to Plymouth.
• Plymouth Long Beach is a 3-mile long stretch of public beach that’s perfect for getting out by the water.
• Plymouth Farmer’s Market is held every Thursday from May through October, and was Yankee Magazine editor’s pick for best Farmer’s Market in 2018.
• Brewster Gardens is a tranquil, waterfront park that’s sure to invite lots of relaxation.
• Walk around the charming downtown to visit the shops and restaurants,
• Pop into Dirty Water Distillery for an artisanal spirits tasting.
• Go on a whale watch tour with Captain John’s Boat Tours .
• Spend the day getting pampered at Mirbeau Resort & Spa , and even stay for lunch or dinner, or the night for the ultimate day of relaxation.

Click here to book your stay at Mirbeau Resort & Spa!

Psst! I have an entire post on visiting Plymouth, MA , if you need more ideas!

2. Cape Cod, MA

Distance From Boston: 1-2.5 hours, depending on where you to choose to go on Cape Cod.

With over 500 miles of shoreline to explore, Cape Cod is the ultimate beach road trip from Boston because you can get there in about 2 hours and feel like you’re in a whole other world. There are 15 towns in Cape Cod to choose from for your visit, and more beaches than anyone can count. Fill your days being ocean-side, exploring beautiful little coastal towns, eating fresh seafood and taking in amazing sunsets.

Best Things To Do on Cape Cod :

• Visit The Cape Cod National Seashore
• Explore Chatham’s downtown
• Visit Provincetown and the Pilgrim Monument
• For more on the best things to do on the Cape, click the link below for my detailed travel guide.

You may also enjoy:

• Can’t Miss Things To Do When Visiting Cape Cod For The First Time
• Best Things To Do On Cape Cod For Adults
• Best Towns To Stay In On Cape Cod
• What To Pack For Cape Cod
• Unique Things To Do On Cape Cod

3. Nantucket, MA

Distance From Boston: 2-3 hours, which includes time to park at the ferry terminal, and ride the ferry.

Nantucket is a gorgeous island off the coast of Cape Cod bursting with charm and natural beauty. A day trip to Nantucket is common while visiting Cape Cod, but staying overnight for a night or two would be the best way to make the most of your road trip from Boston. This is a great island to explore if you’re looking for stunning beaches and a beautiful downtown area.

To get to Nantucket, you’ll need to take the ferry from Hyannis on Cape Cod. From there, you can choose between Hyline Cruises or Steamship Authority to get to Nantucket.

Best Things To Do on Nantucket:

• Explore the shops and restaurants in the main town.
• Visit Brant Point Lighthouse.
• Rent a moped to explore the local beaches and towns.
• For more amazing things to do on Nantucket, click the link below for my detail travel guide on a Nantucket day trip.
• The Best Nantucket Day Trip Travel Guide
• How Many Days Do You Need On Nantucket + Suggested Itineraries
• How To Visit All The Nantucket Lighthouses

4. Martha’s Vineyard, MA

Martha’s Vineyard is the other island off the coast of Cape Cod, and it’s more popular as an overnight destination, versus a day trip because it’s bigger. Comprised of 6 beautiful towns, Martha’s Vineyard is home to beautiful beaches, quaint Main Streets for shopping and dramatic cliff-lined shores.

To get to Martha’s Vineyard, you’ll need to take a ferry from either Woods Hole or Hyannis (both terminals located on Cape Cod). There is no benefit to picking one over the other, and it’s best to just pick whichever location is more convenient for you (usually it’s Hyannis for most people).

Best Things To Do on Martha’s Vineyard:

• Gingerbread Cottages in Oak Bluffs
• Edgartown downtown and lighthouse
• Aquinnah Cliffs and Gay Head Lighthouse
• South/Katama Beach
• For more information on visiting Martha’s Vineyard, click the link below for my guide on deciding between Nantucket or Martha’s Vineyard for a day trip.

You may also find these Martha’s Vineyard posts helpful:

• Is Nantucket or Martha’s Vineyard Better For A Day Trip?
• The Ultimate Martha’s Vineyard Day Trip Guide
• How To See Martha’s Vineyard Without A Car

5. Marblehead, MA

Distance From Boston: 40-50 minutes.

Marblehead is an adorable little coastal town along the North Shore of Massachusetts, and a very quick road trip from Boston. This is the place to come if you’re looking for historical homes, small-town charm, great seafood, dramatic, rocky coastline and options for beaches.

Best Things To Do in Marblehead, MA:

• Marblehead Lighthouse & Chandler Hovey Park
• Self-guided historical home walking tour.
• Take in the views at Castle Hill Rock.
• For more information on the best things to do in Marblehead, click the link before for my detailed travel guide.

Click here to read even more awesome things to do in Marblehead!

6. Salem, MA

Distance From Boston: 30-40 minutes.

Salem is another little coastal town along the North Shore of Massachusetts, and is known for being the premier New England destination for all things spooky. While visiting Salem in October is definitely a bucket list-worthy goal, it’s actually a really wonderful town to visit all year round. It’s very walkable with a variety of things to do, and makes for a great day trip, or a weekend getaway.

Best Things To Do in Salem, MA:

• Winter Harbor Park and Lighthouse
• Salem Witch Trials Memorial
• Salem Maritimes National Historic Site
• Essex Street Pedestrian Mall
• House of Seven Gables
• Peabody Essex Museum

Psst! I have some helpful guides including planning the perfect Salem, MA day trip , and the best time to visit Salem if you need more information 😉

7. Rockport, MA

Distance From Boston: 50-60 minutes.

Rockport is one of my favorite coastal towns in all of New England. It has so much character, wonderful shops and restaurants, and really invites you to slow down a bit to take it all in. It’s a small town, and can be done in a day, but a weekend here would be a very relaxing road trip from Boston.

Best Things To Do in Rockport, MA:

• Visit Motif 1, the most painted building in New England, if not the country!
• Go for a scenic walk or hike at Halibut Point State Park.
• Meander through the shops on Bear Skin Neck.
• For more things to do in Rockport and the North Shore region, click the links below for my detailed travel guides.

Click here for more amazing things to do in Rockport!

Click here to read my travel guide on the best things to do on Cape Ann!

8. Newburyport, MA

Newburyport is a delightful little coastal town in Massachusetts that has a very traditional New England feel with beautiful homes at every turn, and an adorable little downtown area and waterfront park. Newburyport is also home to Plum Island, which is a gorgeous part of town with amazing beaches and wildlife sanctuaries.

Best Things To Do in Newburyport, MA:

• Visit Oldies Marketplace to look for antiques and treasures.
• Meander the streets of downtown to explore the beautiful storefronts.
• Take a leisurely stroll along the waterfront park.
• Pack a picnic or take a nature walk at Maudslay State Park , which has over 500 acres to explore.
• Head out on the open waters with Yankee Clipper Tours , and cruise around the Merrimack River and Newburyport Harbor.
• Drive over to Plum Island to visit Plums Island Beach, buy some handmade soaps at Plum Island Soap Co. , and walk the stunning nature trails at the Parker River National Wildlife Refugee .

Click here to read my full guide to visiting Newburyport & Plum Island!

9. Block Island, RI

Distance From Boston: 3-3.5 hours, which includes time to park at the ferry terminal, and ride the ferry.

Block Island is a beautiful island off the coast of Rhode Island with gorgeous beaches, walking trails, water activities, salt marshes, great restaurants and is overall a wonderful place to relax while appreciating the outdoors. This actually might be one of my top underdog suggestions for a weekend getaway from Boston.

It actually reminds me a bit of Prince Edward Island, so if you’re looking to live out your Anne of Green Gables dreams, but can’t make it to Canada, this is a great place to do that. There’s even a lovely hotel on the island called Avonlea.

To get to the island, you’ll need to drive to the Pt. Judith ferry terminal in Rhode Island. For more information on the ferry, click here .

Best Things To Do on Block Island, RI:

• Take in the views at Mohegan Bluffs.
• Rent a moped to explore the entire island.
• Spend some time swimming at Mansion Beach.
• Visit the island’s two lighthouses.
• Have lunch with a water view at The Oar .

Click here to read all my tips for taking a Block Island day trip!

10. Newport, RI

Distance From Boston: 1.5 hours, but always anticipate extra traffic crossing the Newport bridge.

Newport is a stunning coastal city in Rhode Island that’s the perfect destination for sailing, shopping, dining and being by the water. Even though it’s technically a city, I wanted to include it in the coastal destinations group because it definitely feels more like a resort waterfront town than a city.

With so many things to do, you could easily spend a weekend here, but Newport will also work for a day trip.

Best Things To Do in Newport, RI:

• Walk along Cliff Walk for amazing coastal views.
• Visit Bowen’s Wharf for shopping and dining.
• Grab a lobster roll at the Newport Lobster Shack .
• Walk over to Goat Island to see the lighthouse and take in views of the Newport Bridge.
• Sail around Narrangansett Bay with Sightsailing of Newport .
• Visit the unique shops along Thames Street.
• Grab lunch and cocktails at The Lawn at Castle Hill Inn , overlooking the water. Better yet, book an overnight stay for the ultimate Newport experience!

Click here to book your stay at The Castle Hill Inn in Newport .

Click here to read all my tips for taking a Newport, RI day trip!

Click here to read about all the best things to do in Newport, RI in the winter!

11. Mystic, CT

Distance From Boston: 1.5 hours

This adorable little town sits along Mystic River, and has an awesome mix of preserved maritimes history, small-town charm and nature. While Mystic is mostly visited for its quaint, waterfront downtown, it’s also home to parts of two bordering towns, Stonington and Groton, giving you opportunity to explore a few different coastal Connecticut destinations during your visit.

Best Things To Do in Mystic, CT:

• See penguins, beluga whales, sharks and sea lions at the Mystic Aquarium .
• Learn all about maritimes history at the Mystic Seaport Museum and Village , which is regarded as one of the best, if not the best, Maritimes museums in the country.
• Hit the trails at Bluff Point State Park.
• Take a sunset or moonlit cruise with Poet’s Lounge Sailing Charters .
• Grab a warm lobster roll, which originated in CT, at Ford’s Lobster in nearby Noank.

Click here to read about all the best things to do in Mystic, CT!

12. The Hamptons, NY

Distance From Boston: 5.5 hours if driving the whole way, 6 hours if you drive to New London, CT to take the ferry.

The Hamptons needs no introduction, as it’s become a famous summer destination in New York thanks to many celebrities calling it a secondary home. Sitting along the Long Island sound, you can expect gorgeous beaches, amazing shopping and restaurants, specialty food markets and farmer’s markets, wineries and plenty of opportunity for rest and relaxation.

The Best Things To Do in The Hamptons:

• Have a beach day and watch the surfers at Coopers Beach in Southampton.
• Go vineyard hopping, and taste some of the local wines. Channing Daughters Winery and Wölffer Estates are two great options.
• Take in the views at Montauk Lighthouse.
• Enjoy an afternoon of rest and restoration at the Montauk Salt Caves .
• Have some amazing and fresh seafood at Bostwick’s Chowder House in East Hampton.
• Rent a bike and ride along Gin Lane in Southampton for incredible views of the ocean, and to see some amazing houses.

13. Ogunquit, ME

Distance From Boston: 1 hour and 15 minutes

One of my favorite beach towns in all of New England is Ogunquit, which is one of the best places to visit in Maine in the summer , but it’s really fun in spring and fall, too. Offering both dramatic and rocky coastline that Maine is famous for, as well as a long, sandy beach that’s perfect for swimming, you’ll get the best of both worlds here. Ogunquit’s town is entirely walkable, so once you drive in, you’ll be able to leave your car behind and get almost everywhere by foot. There’s an amazing downtown scene with plenty of shops and restaurants, and you’re never that far from Ogunquit Beach.

Best Things To Do in Ogunquit, ME:

• Walk along Marginal Way, where you’ll get the most amazing views of the rocky coastline.
• Visit Perkins Cove to enjoy its charming shops and restaurants.
• Spend plenty of time at Ogunquit Beach, one of the best beaches in Maine.
• For more information on things to do in Ogunquit, click the link below for my detailed travel guide.

Click here to read about more amazing things to do in Ogunquit!

14. Kennebunkport, ME

Distance From Boston: 1 hour and 25 minutes

Just a short distance from Ogunquit is Kennebunkport, so these two destinations could easily be combined, and both are worth your time. Kennebunkport is full of character, and can be visited as either a day trip, or a weekend getaway, from Boston. Offering both beaches and a wonderful downtown scene, this is a great place to relax, unwind and enjoy being by the water.

Best Things To Do in Kennebunkport, ME:

• Visit Gooch’s Beach for a walk along the shore, or go for a swim.
• Have an authentic lobsterman experience with Rugosa Lobster Tours .
• Walk around the downtown and Dock Square shops.
• Grab an artisanal ice cream cone at Rococo Ice Cream .
• Have some craft cocktails and beer at Batson River Brewing and Distillery .
• Walk along Parson’s Way for amazing views of the dramatic coastline.
• Grab fresh seafood takeout from The Clam Shack .

Click here to see why Kennebunkport is one of the best Christmas towns in New England!

15. Bar Harbor/Acadia National Park

Distance From Boston: 4 hours and 45 minutes

One of the absolute best places to visit in all of Maine is Bar Harbor and Acadia National Park, and this will make an epic road trip from Boston. Bar Harbor is the adjacent town to Acadia, and where most people stay when visiting the park. Bar Harbor is a fun destination on its own because it’s full of character, and has great restaurants, and a beautiful harbor-side walking path and park.

Acadia National Park is one of the top destinations in all of New England, providing over 120 miles of hiking trails, and countless opportunities to take in some of the best and most incredible coastline views in the entire Northeast. In my opinion, this is one of the best roads trips from Boston you can take.

Best Things To Do in Bar Harbor & Acadia National Park:

• Walk along the Ocean Path trail inside Acadia, which is a flat, easy path along Shore Road that provides the most payoff for minimal effort when it comes to the most famous views in the park.
• Have lunch and popovers at Jordan Pond House inside Acadia, which offers views of the lawn and Jordan Pond.
• Drive to the summit of Cadillac Mountain inside Acadia for sunrise or sunset.
• Explore Bar Harbor’s downtown.
• Take a leisurely walk along Shore Path in Bar Harbor for the best views of the harbor.
• Visit Bass Harbor Lighthouse inside Acadia.

Tip : You’ll need to purchase a park pass to enter any attractions inside Acadia National Park. Park passes can be purchased online in advance by clicking here .

Psst! I have some posts on Acadia that you may find helpful, including my Acadia National Park Itinerary , and the Best Time To Visit Acadia National Park .

Luxury Road Trip Destinations From Boston

These destinations don’t have to be all about luxury, but since it’s nice to treat yourself every now and then, I wanted to include a few of my favorite luxury resorts that are easy road trips from Boston. If all you’re looking for is a little R&R and some serious pampering without having to leave the resort grounds, these are amazing places to visit.

16. Cliff House in Cape Neddick, ME

If you’re looking for the ultimate coastal Maine getaway to fully relax and recharge, then Cliff House will be the perfect road trip from Boston for you. This oceanfront resort sits atop 70 acres of cliffs, and offers incredible amenities that will allow you fully emerse yourself in Maine’s natural beauty without having to go far. Almost every square foot of this property has an ocean view, so there’s no way you can be stressed during your visit.

What To Expect During Your Stay At Cliff House:

• Beautifully-appointed rooms with a private terrace, and your choice of partial or full ocean views. Some rooms are also ocean-front.
• Complimentary coffee, tea and water stations on each floor.
• A full-service spa.
• Three oceanfront restaurants and a coffee cafe.
• Manicured gardens and pathways for relaxing walks.
• Two outdoor pools, two indoor pools and a hot tub.
• On-site shopping.

Click here to book your stay at Cliff House!

17. Ocean House in Westerly, RI

Distance From Boston: 1 hour and 45 minutes

For one of the very best luxury experiences in all of New England, Ocean House in Westerly, RI is a truly amazing destination. With the entire properly overlooking the Block Island Sound, it’s guaranteed you’ll be able to relax during your stay. Travel + Leisure has even named Ocean House as one of the top 100 hotels in the entire world.

What To Expect During Your Stay At Ocean House:

• Freshly designed and elegant coastal New England rooms and suites.
• Complimentary use of the hotels Mercedes-Benz convertibles for self-guided tours.
• Complimentary activities within the resort, such as daily yoga and cooking classes.
• Valet parking included in your room rate.
• Four on-site restaurants, and lobster dinners on the lawn during the summer.
• An on-site spa.
• Beautifully manicured lawns with yard games.
• Complimentary refreshments throughout the day.

Click here to book your stay at the Ocean House!

18. Mohonk Mountain House in New Paltz, NY

Distance From Boston: 3 hours and 45 minutes

If you’re looking for the ultimate road trip from Boston that combines hiking in the mountains with total relaxation, then Mohonk Mountain House is perfect for you. Located in the small college town of New Paltz, Mohonk Mountain House is right in the heart of the Hudson Valley of New York, and is surrounded by 40,000 acres of forest.

Overviews of the resort have been used in the Amazon Prime series Upload , and has long been rumored to be the inspiration behind Stephen King’s The Shining . But don’t let that scare you away! That only thing that will actually scare you once here is how amazing the views are.

If an overnight stay doesn’t work with your plans, guests can also purchase a day pass to the resort grounds, which allows you access to the hiking trails. This is a great way to enjoy the scenery without committing to an overnight stay.

What To Expect During Your Stay At Mohonk Mountain House:

• Traditionally-decorated rooms and suites that overlook the mountains. Most rooms also come with private balconies and rocking chairs.
• Lake Mohonk on the resort grounds.
• An all-inclusive stay where breakfast, lunch, afternoon tea and dinner, as well as all outdoor activities such as kayaks, row boats and canoes, are all included in the room rate.
• 85 miles of hiking trails right outside your door.
• Farm-to-table dining.
• Benches and chairs situated all over the resort grounds for moments of rest, and to clear your mind.

Click here to book your stay at Mohonk Mountain House!

Click here to read my detailed review of a Mohonk Mountain House Day Pass!

19. Mirbeau Spa in Rhinebeck, NY

Distance From Boston: 3 hours and 10 minutes

Mirbeau has a few locations throughout the Northeast, but my favorite of them all is in Rhinebeck, NY, a beautiful little town in the Hudson Valley. This particular Mirbeau Spa is one of the newer additions to their family, and is decorated in a modern, Parisian style, which makes it feel like a unique destination.

The spas at Mirbeau are really amazing. I’ve personally had massages and treatments at different locations, and they’ve always been consistent in quality (and, of course, relaxation). Guests are invited to walk around in robes, including at lunch, and the on-site hotel allows you to continue your relaxation journey into the evening for the perfect overnight stay.

What To Expect During Your Stay At Mirbeau in Rhinebeck, NY:

• A serene, calm spa atmosphere throughout the entire grounds.
• A relaxation room, aqua terrace and steam facility within the spa.
• Different spa packages to customize your stay that include dining options to make your visit stress-free.
• Luxurious and Parisian-inspired accommodations with options including in-room fireplaces and soaking tubs.

Click here to book your stay at Mirbeau in Rhinbeck!

Charming Small Town Road Trip Destinations From Boston

If you’re looking to visit some of the most charming towns in New England and New York for your road trip, I’ve got your covered! Here are the most adorable little towns to visit that make awesome road trips from Boston.

20. Saratoga Springs, NY

Distance From Boston: 3 hours and 15 minutes

While technically a city, Saratoga Springs’ historic downtown feels very much like a quaint village. Located in Upstate, NY and known for its horse racing track season, this destination has so much more to offer including a wonderful Main Street for shopping and dining, gorgeous parks, beautiful and historic architecture and live entertainment.

Best Things To Do in Saratoga Springs, NY:

• Walk around the grounds of Saratoga Spa State Park, which is a National Historic Landmark. You can enjoy a round of golf at an 18-hole championship course, have a picnic by the reflecting pool and admire the architecture of the Hall of Springs.
• July – Labor Day, visit the Race Track , and even try your hand at placing bets on the winner!
• Stroll through Congress Park, and find the mineral springs to taste the local water.
• Enjoy a healing bath at the Roosevelt Baths & Spa . The spa staff is trained on how to draw the perfect bath at just the right temperature, and the minerals in the waters have been said to have health benefits such as reducing sinus congestion and arthritis symptoms.
• Take in a live show at SPAC , one of the the country’s most renowned outdoor concert venues.
• Walk up and down Broadway, downtown’s main street, to visit the local shops and restaurants.
• Grab delicious cocktails with lunch or dinner at Morrissey’s Lounge & Bistro inside the famed Adelphi Hotel. Better yet, book an overnight stay at this Gilded Age-era boutique hotel, located in the heart of Saratoga’s downtown.

Click here to book your stay at the Adelphi Hotel in Saratoga Springs!

21. Skaneateles, NY

Distance From Boston: 5 hours and 20 minutes

Skaneateles is a lakeside town in the Finger Lakes region of Upstate, NY, and is a wonderful place to visit, especially in the Summer. With Skaneateles Lake right in the heart of downtown, and an adorable Main Street with really nice shops and restaurants, the quaintness of the town is perfect for rest and relaxation, but also offers plenty to do to keep from ever being bored.

Best Things To Do in Skaneateles, NY:

• Walk around Main Street to visit the boutiques.
• Sit and admire the views of the lake from the town’s many waterfront areas.
• Visit Anyela’s Vineyards to enjoy a tasting, or sip on a glass of wine and take in the peaceful views of the vineyards.
• Head out onto the lake for a boat tour.
• Grab dinner and drinks at the Sherwood Inn , located right in the heart of town, and just across the street from the lake.
• Spend the day getting pampered at Mirbeau Inn & Spa , the original Mirbeau location, which is home to a Monet-inspired garden and bridge.

Click here to book your stay at Mirbeau Inn & Spa in Skaneateles!

Click here to read more suggestions on the best things to do in Skaneateles, NY!

22. Lake Placid, NY

Distance From Boston: 5 hours

Known for hosting two Olympic games, Lake Placid in the Adirondack region of Upstate NY has so much more to offer (although, the Olympic sites are definitely worth visiting!). I personally love visiting Lake Placid in the winter because the alpine-inspired town really seems to come alive with apres-ski vibes, but it’s really a great destination all year round. While in Lake Placid, you’ll be surrounded by mountains and fresh air, and feel like you’ve truly escaped from every day life.

Best Things To Do in Lake Placid, NY:

• Walk around Mirror Lake, located in the heart of Lake Placid’s downtown.
• In the winter, enjoy skiing at Whiteface Mountain , and ice skating and a Toboggan Chute on Mirror Lake.
• Enjoy the miles of hiking trails in the nearby mountains.
• Walk around the alpine-inspired downtown village to visit the quaint shops.
• In the summer, go for a swim in Mirror Lake from the public beach area.
• Visit the Olympic sites, including the ski jump, ice arena and the Lake Placid Olympic Museum .
• Walk around High Falls Gorge, a 22-acre nature park with waterfalls.
• Grab drinks and lunch or dinner at The Cottage, a restaurant at Mirror Lake Inn Resort & Spa that sits right on Mirror Lake. Better yet, book an overnight stay, and also enjoy the on-site spa for the ultimate Lake Placid getaway!

Click here to book your stay at the Mirror Lake Inn Resort & Spa in Lake Placid .

Click here to read my post on all the best things to do in Lake Placid in the fall!

23. Hudson, NY

Distance From Boston: 2 hours and 45 minutes

Located in the Hudson Valley of New York, Hudson is known as being incredibly charming, and one of the best destinations for antiquing in the area. This is a great little town to visit if you’re looking to relax, enjoy a small-town atmosphere and see where the day takes you. Hudson is also a great destination if you’re looking to explore the entire Hudson Valley region.

Best Things To Do in Hudson, NY:

• Antiquing! There are countless antique shops in Hudson, and you’ll definitely want to check out The Antique Warehouse , which has over 300,000 sq. feet of treasures.
• Stroll down Warren Street, where most of the storefronts can be found.
• Take a boat cruise along the Hudson River with Hudson Cruises , which offers tours to the Hudson-Athens Lighthouse, and even murder mystery cruises!
• The Hudson Farmer’s Market is regarded as one of the best in the region, and is open every Saturday in-season, and also has a winter location February-April.
• Tour the local art galleries.
• Go for a nature walk in the Greenport Conservation Area, which is home to over 7 miles of trails, and is walkable from downtown Hudson.

Click here to read my post on the best things to do in Upstate New York in the fall!

24. Manchester, VT

This small little town in Southern Vermont is the perfect place to disconnect and relax. As you cross the New York/Vermont border, you’ll begin to see the tall mountains all around you, and instantly feel more at peace. In fact, you’ll be able to see the surrounding mountains from everywhere in downtown Manchester. And with everything to do from shopping and dining to hiking and nature walks, you’re sure to find something that everyone in your group will enjoy.

Best Things To Do in Manchester, VT:

• Hike or drive up Mt. Equinox, the tallest mountain in the Taconic Range, and enjoy the incredible views from above.
• Browse through Northshire Bookstore , an amazing independent bookstore that’s been in business since 1976. Here, you’ll find new and used books, a wonderful children’s section, and unique Vermont-inspired gifts and souvenirs.
• Visit Hildene , the Lincoln family estate, where visitors can tour the gardens, walking trails, farm land and indoor exhibits, and enjoy sweeping views of the Vermont countryside.
• Rent a tube at Vermont River Runners and take a relaxing water tube ride along the Battenkill River, which is perfect for a warm summer day.
• Grab a sandwich as big as your head at Zoey’s Deli . I also love their homemade chips!
• Hike the Lye Brook Falls trails to visit a beautiful waterfall. The trailhead is a short 5-minute drive from town center.
• Go for a dip in the Dorset Marble Quarry for a unique swimming experience!
• After your swim, visit the Dorset Union Store , a quintessential Vermont country store.

Click here for an awesome Vermont covered bridges tour itinerary!

25. Woodstock, VT

Distance From Boston: 2.5 hours

Of all the Vermont towns on this list, I think Woodstock might be my favorite. I love them all, but there’s something about Woodstock that just screams New England charm, and perfectly balances being a town that caters to tourists, while not losing any of the local character. It’s one of those idyllic towns you’ll daydream about moving to.

Best Things To Do in Woodstock, VT:

• Walk through the truly adorable village and enjoy the local shops and coffee cafes.
• Head over to the Woodstock Middle Covered Bridge, located right in the village, for a picture-perfect Vermont moment.
• Get your hands muddy with a pottery workshop at Farmhouse Pottery .
• Drive to nearby Quechee and visit the Simon Pearce Restaurant & Mill , and take in a live glass-blowing demonstration, as well as lunch overlooking the gorge.
• Head over to Quechee Gorge Village after Simon Pearce for some antiquing.
• Visit Billings Farm & Museum to tour a working dairy farm, gardens and orchards, and see live demonstrations. The grounds here are truly spectacular!
• Hike Mount Tom for stunning views of Woodstock from above.
• Best Places To Stay In Vermont In The Fall
• Best Things To Do In Woodstock, VT
• Best Winter Getaways In New England

26. Stowe, VT

Distance From Boston: 3 hours and 20 minutes

Stowe is an adorable little village in Northern Vermont that I love to visit, and it always puts a smile on my face. Even though it’s a well-known ski destination in the winter months, it’s a great little place to visit year-round will lots of outdoor activities and perfect Vermont scenery all over, including some beautiful covered bridges.

Best Things To Do in Stowe, VT:

• Hike Mount Mansfield, the highest mountain in Vermont, or drive the auto road to the summit.
• See if you believe in ghosts at Emily’s Covered Bridge. Legend says it’s haunted by a girl who hung herself on the bridge after her boyfriend never came to meet her.
• Walk the Stowe Recreation Path, a 5.5-mile long paved path that goes through beautiful scenery throughout the village. The path can be accessed from several locations in the village.
• Connect to the Quiet Path along the Rec Path, which is reserved for walkers only (meaning, no bikes wizzing by you). It meanders through parts of Mayo Farm, and is a very relaxing way to spend an afternoon.
• Go hiking at Smuggler’s Notch State Park.
• Visit the nearby Ben & Jerry’s Factory for a tour.
• Explore Sterling Falls Gorge.
• In the winter, hit the slopes at Stowe Mountain Ski Resort.
• Pick up some chocolates from Lake Champlain Chocolates.
• Best Things To Do In Stowe, VT
• Best Stops To Make When Driving From Boston to Stowe, VT
• Best Things To Do In Vermont In The Winter

27. Greenwich, CT

Distance From Boston: 3 hours

Greenwich is an absolutely beautiful town that sits right on the border of New York, and also very accessible to Manhattan. I love coming to this idyllic little town when I want a day of relaxing, shopping, dining, being outside, visiting the beach and enjoying the gorgeous scenery.

Best Things To Do in Greenwich, CT:

• Shop the stores along Greenwich Avenue.
• Enjoy a serene walk through the Donald M. Kendall Sculpture Gardens in nearby Purchase, NY.
• Meander through Montgomery Pinetum, a public park that’s very relaxing, and also has beautiful ponds, nature trails and gardens with an educational center and greenhouse.
• Head to the Lobster Bin for an amazing lobster roll on-the-go.
• Spend some time at the beaches along Greenwich Point Park.
• Admire the architecture of the historic district buildings.

28. Jackson, NH

Let’s head to the White Mountain National Forest in New Hampshire! One of the best towns to stay in is Jackson, where you’ll find a lovely downtown and Main Street, an iconic red covered bridge, and endless opportunities to explore the White Mountains region, including lots of hiking and outdoor activities. While it’s most popular during the winter for skiing, and the fall for foliage season, Jackson can be enjoyed year-round.

Best Things To Do in Jackson, NH:

• Visit Honeymoon Bridge, the town’s famous red covered bridge.
• Drive to the summit of Mount Washington, the highest peak in New England.
• Hike the Glen Ellis Falls Trail.
• Explore the downtown shops and restaurants.
• In the winter, go skiing at Black Mountain. In the summer, the mountain offers horseback riding and lots of hiking trails.

You may also like: The best things to do in New England in the fall!

City Life Road Trip Destinations From Boston

Even though you’re road-tripping from a city already, it’s still exciting to explore a new one. There are quite a few cities that make for amazing road trips from Boston, and many of them can be combined with other destinations from this list to offer the best of city life, and coastal or small-town living.

29. Portsmouth, NH

Distance From Boston: 1 hour

This charming little city is just a short drive from Boston, and definitely feels more like a town than a city. Portsmouth is a port-side city with a gorgeous downtown filled with quaint shops and boutiques, and is known as being a huge foodie destination. This is a great city to visit if you’re looking for a lot of character, and lots of options when it comes to being outside, dining and shopping.

Best Things To Do in Portsmouth, NH:

• Grab some fresh and delicious pastries from Elephantine Bakery , and be sure to enjoy them just outside the cafe in the most adorable little courtyard.
• Shop the boutiques in downtown Portsmouth.
• Walk along Prescott Park, which has over 10 acres of waterfront gardens and paths, and is home to live entertainment in the summer months.
• Take a dip in the water at Great Island Common Park.
• Go brewery hopping, as Portsmouth is home to five breweries.
• Enjoy a drink at the Book & Bar , a combined bookstore, cafe and bar.
• Head out onto the water with Portsmouth Harbor Cruises .
• Visit Portsmouth Harbor Lighthouse.

30. Providence, RI

Providence is the capital of Rhode Island, and also home to famed schools Brown University and the Rhode Island School of Design. It’s also a really fun city to be a tourist! With Providence River running through the city, you still have opportunities to feel like you’re connected to nature, and with tons of restaurants, shops, nightlife and history, this destination makes for an amazing road trip from Boston.

Best Things To Do in Providence, RI:

• Visit The Arcade , the country’s very first shopping mall designed with Greek revival architecture, and now home to some awesome boutiques and art galleries.
• Visit the Roger Williams Park Zoo , which is the third oldest zoo in the country, where guests can feed giraffes and other farm animals, and see over 160 different species while visiting. You can also jump on the Explore and Soar ride, which is a fun zip ride and train excursion through the forests.
• Enjoy a leisurely walk along the Providence Riverwalk.
• During the summer, experience WaterFire, where braziers are set with bonfires in the middle of the river.
• Take in the exhibits at the RISD Museum of Art.
• Take a Venetian gondola ride along the river at Waterplace Park.
• Do a self-guided historical walking tour along Benefit Street to see some of the city’s most historic houses and buildings.
• Take a boat tour along the Providence River.

Click here to read my post on the best day trips from Providence!

31. Portland, ME

Portland is an exciting waterfront city in Maine that sits on a peninsula along Casco Bay, and provides the best of both worlds as far as being a city destination that’s also coastal. With things to do outdoors along the dramatic coastline, to an amazing restaurant and food scene, Portland has a little something for everyone during your road trip from Boston.

Best Things To Do in Portland, ME:

• Portland Head Lighthouse is a must! It’s the most famous lighthouse in Maine, and one of the most iconic in all of New England. Nearby, you can also visit Spring Point Ledge Light and Bug Light, and do a mini lighthouse tour without leaving the city!
• Visit one of my favorite breweries in New England, Bissell Brothers . They also get bonus points for being close to the waterfront at Thompson’s Point.
• Meander around Old Port to see the city’s fishing industry come to life.
• Walk along the lively waterfront scene on Commercial Street for shopping, dining and water views.
• Tour the open waters on a beautiful Schooner tour with Portland Schooner . They also invite you to pack a picnic with beer and wine to enhance your experience.
• Tour the Portland Arts District, which is filled with art galleries, museums and theaters.
• Take a culinary tour of the city and learn the very best places to eat, led by a local. Click the link below to book your tour, or learn more info.

Click here to book your walking culinary tour in Portland!

You may also like:

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32. New York City

Distance From Boston: 3 hours and 45 minutes (but always allow extra time for traffic)

New York City needs no introduction, and if you’ve never been to the city that never sleeps, this is an absolute must if you’re looking into road trips from Boston. Below is a list of my absolute favorite things to do when I visit NYC, which includes the best things to do for first-time visitors.

The Best Things To Do in New York City:

• Walk the Brooklyn Bridge and visit DUMBO for sweeping views of both the Brooklyn and Manhattan bridges.
• Get bagels at Brooklyn Bagel (the best in the city).
• Visit Central park, and be sure to stop at Bow Bridge, Belvedere Castle and The Mall walkway.
• Grab a slice of pizza at Joe’s (150 E 14th St.)
• Explore the MET Museum and Cloisters.
• Take the Staten Island Ferry for views of the Statue of Liberty (this is free and way better than the official tours, which are super crowded!).
• See a broadway show.
• It’s touristy, but I love going to the top of the Empire State Building.
• Walk around the West Village for amazing streets and brownstones.

33. Burlington, VT

Burlington is a small and beautiful city in Northern Vermont that sits along Lake Champlain, and is wonderfully diverse, exuberant and also very relaxing. This is a great destination if you’re looking for a small-town feel set in a bigger city, waterfront and outdoor activities, an art scene and plenty of amazing restaurants.

Best Things To Do in Burlington, VT:

• Walk around Church Street, a pedestrian-only area lined with unique shops and restaurants.
• Stroll around the waterfront to admire the views of Lake Champlain, as well as the Burlington Breakwater Lighthouse.
• Bike the Burlington Bike Path, a beautiful path along the lake that’s over 7 miles long.
• Go kayaking or stand up paddleboarding on the lake.
• Head to nearby Shelburne to tour Shelburne Farms , one of my favorite things to do in all of Vermont! There are tons of hiking and walking trails through the 1400-acre picturesque grounds, and you can stop to sample their homemade cheeses and baked goods along the way.
• Take in the art scene on the South End, which is loaded with galleries and shops.
• Get a taste for the local brews with a Sip of Burlington Beer Tour. Join a small group for dinner, and learn from a local brew expert as you taste all the different beers that are brewed nearby. Click the link below to learn more, or book your tour.

Click here to book your Beer of Burlington experience!

34. Philadelphia, PA

Last but most definitely not least on our round-up of the best road trips from Boston, is the city of Brothery Love, Philadelphia. Philly is Pennsylvania’s largest city, and is deeply rooted in history, but there are all kinds of things to do from exciting nightlife and amazing food to parks and waterfront activities.

Best Things To Do in Philadelphia, PA:

• Run up the Rocky Steps at the Philadelphia Museum of Art, and snap a picture with the Rocky statue. A bit touristy, but if you’re a fan of the movie, you gotta go for it.
• Speaking of the Philadelphia Museum of Art , after your Rocky moment, be sure to visit. They have an amazing American art collection, as well as works by famed impressionists Renoir, Degas and Monet.
• Tour Independence Hall, regarded as the birthplace of the United States, and where the Declaration of Independence was debated by our Founding Fathers.
• Venture just outside the city to visit Longwood Gardens, an expansive garden oasis filled with both indoor and outdoor gardens and, and beautifully designed grounds.
• Grab a Philly cheesesteak at Woodrow’s Sandwich Shop .
• Stroll along the Delaware Riverfront to explore Cherry Street and Race Street Piers, and take in amazing views of the Benjamin Franklin Bridge.
• Hop on a BYOB trolley tour of the city, hosted by hilarious guides that share historic and entertaining information, and take you to some of the top sites in the city. Click the link below to learn more, or book your tour.

Click here to book your Historically Hilarious Trolley Tour in Philadelphia!

Road Trip Itinerary Options

If you’re looking to combine towns from this list into longer roads trips, or are wondering which towns are close enough to combine together to maximize your time and cover the most ground, I’ve got you covered! Below you’ll find suggested itineraries with different routes you can take while planning the best road trips from Boston.

Option 1: Massachusetts North Shore Road Trip From Boston

For this route, you’ll head north from Boston and visit the following destinations:

• Newburyport & Plum Island
• Portsmouth, NH

Days Needed For This Route: 2-4 . If you’re looking for an easy road trip from Boston with lots of options, this is an awesome route to take. You can do it in as little as 2 days for a weekend trip, or add on two additional days to take your time and explore each town.

Option 2: Cape Cod & The Islands Road Trip From Boston

For this route, you’ll head south from Boston and visit the following destinations:

• Martha’s Vineyard

Days Needed For This Route: 7-8 days. Because this route requires ferries from Cape Cod to the islands, and with Cape Cod being a larger region to explore, I recommend a week.

If you have less time, the islands could be done as day trips, and you could attempt this route in about 5 days . If you have 10 days, I would suggest spending one night in Plymouth, 5 days on Cape Cod, two nights on Nantucket and two nights on Martha’s Vineyard for the ultimate Cape Cod road trip.

Option 3: Boston To Bar Harbor Road Trip

This route will take you up the coast of Maine and stop in these destinations:

• Newburyport, MA
• Ogunquit, ME
• Kennebunkport, ME
• Portland, ME
• Bar Harbor, ME

Days Needed For This Route: 7-10 days. I suggest this much time because your final destination, Bar Harbor, is home to Acadia National Park, and there’s so much to see and do just in the park. And each stop along the way is a very worthy destination to spend at least one night in.

If you’re very short on time, you can do this route in 4 nights with this itinerary:

• On your way to Ogunquit, pass through Newburyport and spend 2-3 hours there. Arrive in Ogunquit late afternoon to spend the night.
• The next day, spend the morning in Ogunquit, and then drive to Kennebunkport to spend about 3 hours exploring there. Drive to Portland, and spend the night.
• The next day, spend your morning in Portland, and then drive to Bar Harbor to arrive by mid-afternoon. Spend 2 nights in Bar Harbor.
• Drive back to Boston.

I have a detailed Boston To Bar Harbor, Maine Road Trip Itinerary if you’d like more help with planning!

Option 4: Vermont Road Trip From Boston

For this route, you’ll head northwest of Boston, and drive through the best towns in Vermont from this list. You’ll cover these destinations:

• Manchester, VT
• Woodstock, VT
• Burlington, VT

Note : This route isn’t as direct as the other routes, and will include 6.5 hours of driving time to get from Boston to Burlington, stopping at the other destinations along the way. But then you can drive direct from Burlington to Boston on your way home, which will only take 3.5 hours.

Days Needed For This Route: 3-5 days . This could easily be a long weekend itinerary if you don’t stop in each town overnight, and just visit Manchester and Stowe for a few hours each. You could, of course, take your time, and do up to 5 nights for this itinerary.

Option 5: Rhode Island & Coastal Connecticut Road Trip From Boston

This route will take you southwest from Boston, and you’ll visit these destinations:

• Providence, RI
• Newport, RI
• Block Island, RI
• Westerly, RI

Days Needed For This Route: 3-6 days . This is another itinerary you could also do in a weekend if you only spend a few hours in Mystic, as a day trip from Newport, and skip going to Block Island. To visit all these destinations, you’ll need about 5 days, but 6 would be ideal to not feel rushed.

Tip : If you wanted to extend your road trip further along this route, there is a ferry that leaves from New London, CT, and goes to the Hamptons!

Option 6: Boston To New York City & The Hamptons Road Trip

This route will take you to these destinations:

• Rhinebeck, NY
• New Paltz, NY
• New York City
• The Hamptons
• Optional add-on: Philadelphia, PA

Note : The route from Boston to The Hamptons, while making all the stops in the Hudson Valley in-between, is not direct, and will take about 7.5 hours without stops, so I highly suggest you stop overnight in at least one of the towns to break up your drive. If you wanted to visit Philadelphia, this would be the route you would want to add that destination to, as you will have to drive through NYC to get there.

Days Needed For This Route: 1 week. To do this route in 7 days, I would suggest spending a few hours each in Hudson and Rhinebeck, then spend the night in New Paltz (splurging at Mohonk Mountain House is definitely worth it!). Then drive to NYC the next day, and spend 3 nights there. Then drive to The Hamptons, and spend 3 nights. If you want to add Philadelphia, you’ll want to add an extra night or two.

If you’re short on time and want to do this route in fewer days, I would suggest spending a night in the Hudson Valley (same as above), spend 3 nights in NYC, but include a day trip to The Hamptons. Or, if The Hamptons is of more interest to you, you could spend one night in NYC, and spend a night or two in The Hamptons. And then drive back to Boston.

The other option is to drive direct from Boston to New York City, and leave out the Hudson Valley towns entirely. On that route, your focus would be New York City and The Hamptons.

What Towns Are 1 Hour From Boston?

Plymouth, Salem, Rockport, Newburyport are all within an hour from Boston, and make for wonderful road trips or day trips from Boston.

Towns not mentioned on this list that are also an hour or less from Boston that are perfect for a road trip are Scituate, Gloucester, Manchester-By-The-Sea and Essex, all of which are located in Massachusetts.

What Cities Are 6 Hours From Boston?

New York City, Portsmouth, NH, Philadelphia, PA, Portland, ME, Burlington, VT and Providence, RI are all within 6 hours or less from Boston, and are all included on this list as amazing road trips from Boston.

Is Boston Close To Niagara Falls?

Boston is over 7 hours from Niagara Falls, and for that reason, didn’t make this list of road trips. But if you have extra time, it could be added to a road trip itinerary for Skaneateles, NY and the finger lakes region.

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That’s A Wrap On The Best Road Trips From Boston

As you can see, Boston is really an incredible gateway to all of the Northeast, making it easy to take lots of different road trips. Whether you want to explore the coast of Massachusetts and Maine, go cute-town-hopping through Vermont or visit as many cities as you can, you’re now ready to plan which of these road trips from Boston is perfect for you.

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New England Fall Road Trip Itinerary: 10 Stunning Stops

by Mark and Kristen Morgan

Published: August 23, 2021

There are many places in the world you can see leaves turn in Autumn, but they pale in comparison to one famed and celebrated region in the US northeast where science, nature and climate combine to put on an extraordinary light show each year. We are of course talking about fabled New England and we’re going to show you 10 places you can’t miss when planning your New England fall foliage road trip, with 5 day itinerary, 7 day itinerary and 10 day itinerary examples included to help you nail down the best possible route for your trip.

We will use our first hand experiences from road tripping New England in fall to bring you tips, advice and unmissable stops to take on your visit. This is one of those true bucket list USA road trip experiences in which it pays to be organized, plan effectively and make the most of every day.

So, let’s get stuck into those 10 unmissable stops and planning your perfect New England fall foliage road trip itinerary!

The Science Behind Fall Colors

What do we know about the changing of colors to give ourselves the best chance of being in the right place at the right time?

Well, we know that fall colors peak furthest north and work southward through the latitudes. So for example, the Blue Ridge Parkway in Virginia and North Carolina is gorgeous in fall, but the colors won’t change there until much later in the season.

Also, we know elevation plays an important role in when peak colors will be on display. Colors will change first in mountainous regions of Maine, New Hampshire and Vermont before they do at lower elevations.

But the most important aspects are weather conditions leading into Autumn, and amount of daylight. It all starts way back in Spring! A late Spring or intense Summer drought can potentially delay peak fall colors by a week or two.

Conditions Affecting Predictions For Peak Fall Colors

In addition to elevation, latitude and weather conditions before fall, there are more specific conditions that can affect peak fall once we actually reach Autumn:

• Soil moisture levels
• Amount of sunlight during the day
• Length of night
• Day and night temperature (important)

So what would constitute as perfect conditions for the best chance at ‘peak’ fall colors being their most radiant and predictable?

• Wet and warm Spring conditions
• Summer without drought or unusually high / low temperatures
• Warm Autumn days and cool but not freezing nights

And what causes the colors to change once conditions are right?

Sunlight pumps leaves full of chlorophyll during Spring and Summer. Once daylight wanes in Autumn, so does the amount of chlorophyll.

That leaves room for other pigments in the leaves, such as anthocyanin and carotenoids to shine.

Why Focus On VT, NH, ME and Even NY

The region of New England technically contains 6 states; Connecticut, Rhode Island, Massachusetts, Maine, New Hampshire and Vermont. In fall, this entire region transforms into an adventure playground for leaf-peeping lovers and passionate photographers.

However, there are three New England states among the six that we feel just have to be prioritized for the very best scenery and most radiant colors; New Hampshire, Maine and in particular Vermont.

But we’re also going to throw a curve ball by including a region not technically part of New England (gasp!) … New York’s Adirondack Mountains are a stone’s throw from the border with Vermont and the colors are just as special.

We want you to see the best places in New England when you take your fall road trip, but we would prefer you to see the best colors. That means skipping the likes of Boston, Portland and Providence on this particular visit to the northeast.

They’re all awesome places and we visited them all on our New England road trip in fall. But they don’t have the colors of rural Vermont and New Hampshire, plus we had days to spare.

Here’s why you should focus on the northern parts of New England for a fall foliage road trip:

Vermont’s rolling hills are overflowing with charming rural towns, barns and covered bridges. But the state is 80% covered in forest and that can only mean one thing; spectacular fall foliage everywhere you look.

Further Reading: The best places to visit in Vermont

New Hampshire

New Hampshire mixes excellent hiking options in stunning mountainous areas with staggeringly beautiful fall foliage colors.

It also has one of the best mini road trip routes in New England during fall – the Kancamagus Highway.

Maine is huge. It is much bigger than the other New England states and that means it’s hard to fit most of the northern parts in to your road trip. Unless you have more than 2 weeks of course.

However, Acadia National Park is one of the very best places you can visit in all of New England in fall so if you have the spare time, it’s hard to skip.

New York’s Adirondack Mountains, including Winter olympic town Lake Placid and its surroundings are beautiful in Autumn. The popular mountainous region is incredibly popular thanks to a host of activities and of course glorious foliage colors.

When Should You Plan Your New England Road Trip For Peak Fall Colors?

It is impossible to plan the perfect ‘peak’ fall road trip itinerary in New England. You would need to be in many places at the same time for that to be possible. We’re not quite there, yet!

Historically, the last 2 weeks of September and the first 2 weeks of October are when the colors change. So that would put October 1st in the middle of that and therefore a ‘peak’ fall foliage target.

Science tells us that colors change in the North and at elevation first, eventually working South and to lower levels.

We’ll get into example itineraries below, but here are some rough dates to use for each itinerary time frame working North to South:

• 5 Day New England Fall Road Trip – We would suggest aiming for September 29 through October 3.
• 7 Day New England Fall Road Trip – Add a day either side, so September 28 through October 4.
• 10 Day New England Fall Road Trip – Add a day before and two after, so September 27 through October 6.
• 14 Day New England Fall Road Trip – Add a day before and three after, so September 26 through October 9.

Should You Book Your Trip In Advance?

Here are two scenarios:

• You don’t book in advance and keep an eye on live fall foliage updates to guarantee hitting peak fall. This also means you have flexibility on bad weather days. However, there are very limited hotels available and those that do have rooms will be more expensive.
• You plan and book your whole trip in advance, getting good value in hotels and can relax. But there’s a chance you won’t time it just right and you will have to deal with whatever weather comes your way.

We can’t offer a ‘better’ solution here because both have pros and cons.

Our trip was mainly booked in advance which meant we spent less but we had to put up with a lot of disappointing rain days, as you will see in the photos below!

Need help planning your New England road trip?

Our popular New England fall travel guidebook helps you with planning every aspect of your road trip, including the best places to stop, where to see fall colors, where to eat and stay, itinerary ideas and map!

Top Tips For Planning Your New England Fall Road Trip Itinerary

Finally, before we jump into the 10 unmissable stops and the New England fall road trip itineraries, let’s have a quick look at some important tips to consider when planning your vacation:

• New England is insanely popular in fall.
• Booking accommodation in advance will save you a lot of money.
• Carefully plan where you want to spend each night based around hikes and photography.
• Start in the North and work South through New England.
• Expect frequent rain and clouds in fall and accept that there’s nothing you can do about it!
• Always carry loads of water and snacks in the car.
• Try to find elevated vantage points as often as possible.
• Some of the best and most unique fall photos are along rural country roads.
• You need multiple spare batteries for your camera!
• You can use a drone in many parts of New England for aerial photography.
• Don’t worry if you miss ‘peak’ colors.

Our popular road trip resources:

• Road trip packing list essentials
• How to plan the perfect road trip

10 Places You Can’t Miss On The Best New England Fall Road Trip

Let’s take a closer look at the 10 stops we think are unmissable on a first New England trip to see the fall colors.

1. Lake Placid, New York

Lake Placid of 1980 Winter Olympics ‘Miracle on Ice’ fame is located at the heart of New York’s revered Adirondack Mountains. It is the perfect base for adventure activities throughout all four seasons, from hiking in Summer to skiing in Winter.

The charming town of Lake Placid is an incredibly popular centralized location for leaf peeping in the Adirondacks. As a result, hotels here are in high demand and not cheap from the end of September until mid October. We know from experience when our bank balance took a mighty hit!

Walk around Mirror Lake in town for the easiest way to soak up gorgeous fall colors. If you have time and enjoy challenging hikes, you can’t miss Mount Marcy. It isn’t the prettiest trail but it is the tallest peak in New York.

Things To Do In Lake Placid, NY

• Take a relaxing walk around serene Mirror Lake.
• Visit the Olympic ski jumping complex.
• Photograph John Brown barn.
• Drive to the summit of Whiteface Mountain.
• Take the Cloud Splitter cable car to Little Whiteface.
• Walk through picturesque High Falls Gorge.
• Hike Mount Marcy, the tallest peak in New York.

Where To See Fall Foliage In Lake Placid, NY

• Mirror Lake in town is gorgeous, walk through residential areas surrounded by colorful trees.
• John Brown barn is a hidden gem for fall colors.
• The top of the ski jump provides sweeping views over the Adirondacks.
• Mount Marcy summit is the highest point in the entire region, providing the best views over rolling hills.
• Whiteface Mountain and Little Whiteface offer more stunning views of fall foliage.

Read our Lake Placid guides for more information:

• 10 best things to do in Lake Placid NY
• Mount Marcy complete hiking walkthrough
• 8 best hotels in Lake Placid NY

2. Burlington, Vermont

Burlington in Vermont might not be the first place you think of for a New England fall foliage road trip destination. However, it is one of the easiest places outside of Boston to fly into the region if you are visiting from further afield.

The small town also happens to be filled with beautiful and radiant foliage colors at every turn. From lakeside bike paths to park towers with stunning views, Burlington is the perfect stop off between Lake Placid and the more famous foliage destination of Stowe.

Hotels in downtown Burlington can be limited and expensive in Autumn, so if you are visiting New England on a budget, try looking for hotels in surrounding villages and towns.

Things To Do In Burlington, VT

• Eat, drink and soak up the atmosphere along Church Street.
• Walk through Waterfront Park alongside Lake Champlain.
• Cycle the Burlington bike path to Grand Isle.
• Explore Ethan Allen Homestead and Museum.
• Stand on top of Ethan Allen Tower for amazing views.
• Taste chocolate at Lake Champlain Chocolates flagship store.

Where To See Fall Foliage In Burlington, VT

• Anywhere along the Lake Champlain waterfront where there are trees.
• Ethan Allen Park and the top of the tower in particular have the best fall foliage views in Burlington.
• Ethan Allen homestead and museum are surrounded by beautifully colorful trees.

Read more about Burlington:

• 10 best things to do in Burlington VT
• 8 best hotels in Burlington VT

3. Stowe, Vermont

Stowe is one of the unmissable fall foliage classics on any New England road trip. The white church in town is one of the most photographed churches in the US and almost all of those photographs are taken in fall.

The town is quaint and attractive but be sure to spend the majority of your time up in Stowe Mountain Resort. This is where you will find hikes, Mt Mansfeld, waterfalls and Smugglers Notch.

Colors will change first up in the higher elevations. So, if you’re a little early, head up to the resort. On the other hand, if you’re a little late, stick to the lower elevations around Stowe town for the most vibrant colors.

Personally, we love to hike, we like flying our drone and we enjoy photographing waterfalls. Stowe was one of the best stops on our New England fall road trip circuit for allowing us to do all of those things.

Things To Do In Stowe, VT

• Photograph the famous white church in Stowe town.
• Drive or hike to the summit of Mount Mansfield.
• Drive through stunning Smugglers Notch pass.
• Ride a bike along Stowe Rec Path or Lamoille Valley.
• Take the SkyRide Gondola to Mt Mansfield.
• Hike a wide range of awesome trails.
• Visit both Bingham Falls and Moss Glen Falls.

Where To See Fall Foliage In Stowe, VT

• In Stowe town, the iconic white church backed by a hill of fall colors is unmissable on your New England road trip.
• But the best colors are in Stowe Mountain Resort. The drive up from town is gorgeous.
• No matter how you get to the top of Mt Mansfield, you can guarantee spectacular fall foliage views.
• Smugglers Notch is our top recommendation for Stowe. If you have a drone, this is the place to fly.

Read more about Stowe, Vermont:

• 15 best things to do in Stowe VT
• 12 best hotels in Stowe VT

4. Woodstock, Vermont

Woodstock in central Vermont is arguably the most picturesque and charming town you will visit on your New England fall road trip itinerary. It truly is like something out of a fairytale. We had no choice but to include Woodstock in our popular guide to the 50 best places to visit in the USA .

Remarkably pretty farms with golden leaves dancing in sunlight and reddish-brown leaves covering the ground create picture perfect scenes. Sleepy Hollow Farm and Jenne Road Farm are featured on many fall foliage calendars you will see in shops on your visit to New England.

Don’t miss the many stunning historic covered bridges around Woodstock. Middle covered bridge is right in town, Taftsville and Quechee are very close by and Cornish-Windsor is a 30 minute drive. The beautiful bridge in the photo below is a privately owned bridge near South Woodstock on the main road to Jenne Farm.

Woodstock is one of the more expensive places to visit on a road trip through Vermont, but it is worth taking a hit on the extra chunk of budget. Simply driving around the narrow country roads near Woodstock for a few hours would provide enough fall foliage colors to last a week of photography.

Things To Do In Woodstock, VT

• Walk around the charming town and admire diverse architectural styles.
• Photograph two postcard perfect farms – Jenne Road Farm and Sleep Hollow Farm.
• Visit a host of historic and stunning covered bridges.
• Explore Marsh Billings Rockefeller Park and hike to amazing viewpoint overlooking Woodstock.
• Visit nearby Quechee Gorge and village.
• See Jersey dairy cows at Billings Farm and Museum.

Where To See Fall Foliage In Woodstock, VT

• Woodstock is incredibly photogenic during fall throughout the town and immediate surroundings.
• The lookout over Woodstock from Mount Tom hike is iconic fall photography.
• The best two fall photographs in Woodstock are at Jenne Road Farm and Sleepy Hollow Farm. They are two truly unmissable stops on your New England fall road trip itinerary.
• Drive your car around the narrow rural roads near Woodstock for some of the most special colors.

Read more about Woodstock, Vermont:

• 15 best things to do in Woodstock VT
• 7 best hotels in Woodstock VT

5. Manchester, Vermont

Similarly to Stowe, Manchester is a four season resort with skiing in Winter and hikes during Spring or Summer. In fall, the town located in the heart of Green Mountain National Forest transitions into a colorful paradise for leaf-peepers.

Manchester can be split into the old historic district and the newer modern resort town. The newer part is livelier and closer to amenities but the historic district is quieter, prettier and more colorful.

Use Manchester as a base for one night to explore nearby elevated areas for some of the most expansive views of rolling hills on a New England fall road trip.

Equinox Mountain is the tallest peak in the area. You can hike it or drive it to open up far-reaching views over three US states. But our top tip is to simply stick to the narrow country roads again and you will find more unique fall foliage photographs.

Things To Do In Manchester, VT

• Drive the Skyline Auto Toll Road to Mount Equinox summit.
• Explore Hildene, the Lincoln Family Home.
• Walk around quaint Manchester Historic Village District.
• See the American Museum of Fly Fishing Museum exhibits.
• Buy a book in popular Northshire bookstore.
• Visit nearby covered bridges.
• See the Bennington Battle Monument.
• Visit Robert Frost stone house museum.

Where To See Fall Foliage In Manchester, VT

• Manchester is the heart of the Green Mountains, so the entire area surrounding the town is staggeringly attractive.
• Rolling hills for endless miles covered in glowing fall colors can be seen from any elevated vantage point.
• Equinox Mountain summit provides the best panoramic views over three states.
• Another place you jump in the car and find unique fall photography opportunities on rural roads.
• Manchester Historic Village District is leafy and the church is surrounded by golden yellow leaves.

Read more about Manchester, Vermont:

• 15 best things to do in Manchester VT
• 9 best hotels in Manchester VT

6. Franconia Notch State Park, New Hampshire

Franconia Notch is one of New Hampshire’s premier tourist regions for hiking, picturesque mountains, skiing and of course fall foliage. A two lane highway mountain pass dissects the Kinsman and Franconia mountain ranges, with a number of fantastic recreational stops along the way.

Artists Bluff is a very short but steep hike leading to a rocky ledge. Its summit overlooks Echo Lake and is most popular in fall when the colors change. As you can see, we hiked the trail on an incredibly cloudy and grey day, which doesn’t help with highlighting the beauty of this viewpoint. We have included Artists Bluff in our popular guide to the 50 best hikes in the US .

Franconia Notch State Park is where you will find the stunning Flume Gorge hike. A little over 2 miles of waterfalls, narrow gorges and forested paths welcome thousands of visitors each year. For us, the best part of Flume Gorge were the two ultra-photogenic covered bridges; Flume and Sentinel Pine.

Things To Do In Franconia Notch State Park, New Hampshire

• Hike the short but steep trail to Artists Bluff summit for stunning views.
• Walk through impressive and extremely popular Flume Gorge.
• Hike Cannon Mountain or take the Cannon Mountain Aerial Tramway.
• See a whole host of waterfalls or hike one of a dozen other mountain trails.
• Ski Cannon Mountain Resort in Winter.

Where To See Fall Foliage In Franconia Notch State Park, New Hampshire

• The single most well known fall foliage photograph in Franconia Notch NH is from the summit of Artists Bluff.
• However, don’t miss the chance to walk through the incredibly picturesque Flume Gorge in fall.
• Not only are the colors vibrant, but waterfalls are attractive and two special covered bridges are incredibly photogenic.
• Anywhere at elevation, which means every hike up a mountain side or the tramway with sweeping valley views.

Read more in our Franconia Notch guides:

• Artists Bluff Trail Fall Foliage Hike
• Flume Gorge Complete Hiking Walkthrough

7. Kancamagus Highway, New Hampshire

New Hampshire’s supremely scenic Kancamagus Highway is one of the very best parts of New England to road trip in fall foliage season. We would put it firmly in the category of ‘unmissable’.

The road between Lincoln and Conway NH is only 35 miles long, but it 35 miles of pure foliage bliss. You can either drive it in one go and simply soak up the colors roadside. Or you can stop at a multitude of overlooks, hiking trails, waterfalls, lakes and covered bridges.

If there’s one part of your New England road trip itinerary to time it right for peak foliage colors, you would do well to beat the Kancamagus Highway in its prime.

A note for photographers and videographers – You can use your drone in many parts of the Kancamagus Highway. We captured amazing photographs and videos of endless miles over rolling hills covered in radiant color.

Things To Do On Kancamagus Highway, New Hampshire

• Stop at various high elevation overlooks with spectacular views over White Mountain National Forest.
• Walk to Sabbaday Falls, Champney Falls and Lower Falls.
• Hike Lincoln Woods or Mount Chocorua.
• Walk out on Rocky Gorge boulders.
• Photograph Russell-Colbath House and the picture perfect Albany Covered Bridge.
• Explore ponds and lakes to your hearts content.

Where To See Fall Foliage On Kancamagus Highway, New Hampshire

• Views over rolling hills from every overlook are astonishing in fall.
• Once the Kancamagus Highway reaches its highest elevation, you will see an ocean of color in all directions.
• Walk through any forest trail or along any waterfall hike to immerse yourself into those foliage colors.
• Albany covered bridge is one of the most picturesque bridges you will find in New England.
• Rocky Gorge and nearby lake with reflecting fall colors are wonderful.
• Even on both ends of the road in Lincoln (Loon Mountain) and Conway the colors are vibrant.

Read more about the Kancamagus Highway:

• 13 best places to stop along the Kancamagus Highway in fall

8. Mount Washington, New Hampshire

At 6,288 ft tall, Mount Washington is the tallest peak in Northeastern United States. It is renowned for wild and unpredictable weather, including the recording of a world record wind speed over over 230 mph.

As our images indicate, Mount Washington can be very wet and cloudy in Autumn. But if you get slightly more luck on your road trip and time it on a sunny day, you will enjoy some of the most beautiful colors and scenery in the entire region.

Avid hikers can climb to the summit, otherwise you can take a historic cog rail train or drive up an auto toll road to reach the top. Views from almost 2,000 meters high over an ocean of bright colors are incredible.

Things To Do Around Mount Washington, New Hampshire

• Hike a very challenging but rewarding trail to the summit of Mount Washington.
• Consider a night hike, fall colors won’t matter in the dark but it is hugely popular for astro and sunrise photography.
• Alternatively, drive the Mt Washington Auto Road to the summit.
• Or, take the most scenic and historic route to the top – by Cog Railway.
• Conway scenic railroad nearby ventures deep into fall foliage forest.
• Endless miles of hiking, 100 waterfalls and a handful of covered bridges to discover.
• Crawford Notch State Park is close by and features more views, hikes and waterfalls.

Where To See Fall Foliage Around Mount Washington, New Hampshire

• Just gain elevation in the White Mountains and you’ll open up valley views with a sea of foliage colors.
• Mt Washington summit is the iconic NH vantage point for sweeping Autumnal vistas.
• For a unique experience, the Conway Scenic Railroad cuts through some of the best colors in NH.
• Crawford Notch State Park is stunning in fall, with fantastic valley views from hikes.

9. Lake Winnipesaukee, New Hampshire

Heading due South of Mt Washington you will find Lake Winnipesaukee encircled by gorgeous fall foliage colors. Unfortunately for us, the rain was back in full swing but you can still see how vibrant the colors are in this area.

You can drive an 81 mile loop road around the entirety of the lake, or take to the waters aboard M/S Mount Washington cruise boat.

Visit Castle in the Clouds for family entertainment and hiking, Weirs Beach for arcades or Wolfeboro for a more relaxing experience. The most popular trail in the area is Mount Major, which we highly recommend for hikers looking for excellent views over the lake.

Things To Do Around Around Lake Winnipesaukee, New Hampshire

• Take a cruise on the M/S Mount Washington.
• Or rent a boat of your own for the day.
• Ride the Lake Winnipesaukee scenic railroad.
• Try your hand at arcade games in Weirs Beach.
• Hike the popular half day trail to Mount Major summit for fantastic lake views.

Where To See Fall Foliage Around Lake Winnipesaukee, New Hampshire

• Elevation is your fall foliage friend around the lake if you want expansive views.
• Mt Major is the perfect moderate hike to include on your New England fall road trip itinerary.
• But nearby Belknap Mountain is also a popular choice for fall hikers.
• Gunstock Mountain Resort has zip lines and ski lifts for easy elevation gain.
• For easier and more close up Autumnal color vistas, simply hire a boat on the lake and explore.
• Or sit back, relax and soak up the views on Lake Winnipesaukee scenic railroad foliage tour.

10. Acadia National Park, Maine

Acadia finds itself in the list of top 10 most visited and best US National Parks each year. Millions of tourists descend on Bar Harbor annually to enjoy a diverse range of amazing things to do inside the awesome park.

Varied hikes suitable for all ages and abilities, including the famous adrenaline pumping climbs Beehive Trail and Precipice Trail , are a huge draw. But despite being a typical Summer destination in the north of America, Acadia is equally as popular in Autumn and that is purely down to its glowing fall foliage colors.

Sunrises from Cadillac Mountain or Schoodic Point can be extraordinarily beautiful if conditions are right, and sunset at Bass Harbor Head Light is a very highly regarded spectacle. You will need to bring your best hiking gear, spare camera batteries and a lot of energy to the wonderful National Park in Maine.

The only problem you will face with including Acadia on a New England fall foliage road trip is its location. You will have a long drive to and from Acadia from Vermont or New Hampshire. However, if you have the time, it is unquestionably worth the extra effort.

Things To Do In Acadia National Park, Maine

• Hike various amazing trails from easy to hard (to exhilarating!).
• Photograph stunning sunrises, landscapes and Bass Harbor Head Light.
• Drive to Cadillac Mountain summit, the tallest peak on the US east coast.
• Walk or cycle maze-like carriage roads through the park.
• Explore Jordan Pond and swim in Echo Lake.
• Eat and drink in glitzy Bar Harbor, Maine.

Where To See Fall Foliage In Acadia National Park, Maine

• Mountain summits from any hike opens up special views over rolling hills covered in fall colors.
• Carriage roads are the perfect way to explore forested trails which are surrounded by trees.
• Drive the national park loop road for easiest access to fall colors.
• Jordan Pond in particular is encircled by vibrant autumnal hues.
• Cadillac Mountain summit opens up 360 degree views over Maine and the ocean.

Read our Acadia National Park guides to learn more:

• 17 best things to do in Acadia National Park
• 10 hikes you can’t miss in Acadia National Park
• Where to stay in Bar Harbor and Acadia National Park
• 10 key things to know about visiting Acadia in the fall

Planning Your New England Fall Road Trip Itinerary

New England is an enormous region and choosing exactly where to visit can be challenging. Here are a few questions to ask yourself before you begin plotting a route:

• Which places are top of your list? Vermont? New Hampshire? Acadia?
• How many days can you spare on your trip?
• Do you want to book accommodation in advance or take it day by day?
• Are you in New England solely to see and photograph fall colors?
• Or are you focused primarily on hiking with colors as an added bonus?
• Do you want to use small and quaint towns as your main places to stay?
• Or are you more interested in being rural and remote each night?
• What is your budget? Can you afford to splurge on activities?

Once you have an idea about how you see your road trip panning out, use that idea as a guide to make the best decisions based on your travel style.

Next, we will go through a number of potential scenarios for 5 day, 7 day and 10 day road trip examples through New England in fall.

Use the examples as a reference but remember, they are generic and based on how we personally would plan our itineraries with hikes and photography in mind.

5 Day New England Fall Road Trip Itinerary

Only having 5 days isn’t as much of a negative as it might usually be. Yes, you are going to have to be selective and it is going to be none stop action. But one of the major benefits to a road trip in fall is that all of the best scenery is seen when driving.

Also, the smaller states of Vermont and New Hampshire don’t require a huge amount of drive time between their most scenic places for fall foliage. Include Lake Placid in the Adirondacks and you can easily tick off most of the places in our list in 5 days.

Another consideration is with just 5 days you don’t need to worry as much about ‘following’ peak fall colors. They won’t change too much in that time frame when compared to 10 days.

Example 1 – Lake Placid NY to Manchester VT

D1 – Lake Placid : Walk around Mirror Lake, drive up Whiteface Mountain and explore High Falls Gorge. Stay in Lake Placid.

D2 – Burlington and Stowe : Walk down Church Street, cycle Burlington bike path, explore Smugglers Notch and Stowe Mountain Resort, sunset at Stowe church. Stay in Stowe.

D3 – Franconia Notch and Kancamagus Highway : Hike artists bluff trail, walk around Flume Gorge, drive Kancamagus Highway and down to Wolfeboro. Stay in Wolfeboro on Lake Winnipesaukee.

D4 – Lake Winnipesaukee and Woodstock VT : Spend morning exploring the lake or hike Mt Major, then drive to Woodstock in Vermont via Cornish-Windsor covered bridge, Quechee Gorge and Taftsville covered bridge.

D5 – Woodstock and Manchester : Visit the farms near Woodstock, drive through Green Mountains to Manchester and end at the top of Equinox Mountain.

You could start and end in New York City if flying into Newark or JFK works from your origin and budget. Alternatively, Montreal would be a better place to start for Lake Placid, hire a car and drop it off in NYC or Boston after leaving Manchester, VT.

Example 2 – Lake Winnipesaukee NH to Manchester VT

D1 – Lake Winnipesaukee : Explore the lake, hike Mt Major, take a cruise and stay in Wolfeboro.

D2 – Kancamagus Highway and Franconia Notch : Drive Conway to Lincoln across Kancamagus Highway, hike Flume Gorge and Artists Bluff. Sleep in Franconia.

D3 – Stowe and Burlington : Stowe church, hike to waterfalls in Stowe Mountain Resort, drive Smugglers Notch and on to Burlington. Ride the bike path for sunset. Stay in Burlington.

D4 – Lake Placid : Whiteface Mountain, High Falls Gorge, Ski Jump and Mirror Lake. Or hike Mount Marcy instead but that is a full day commitment. Stay in Lake Placid.

D5 – Woodstock and Manchester : Visit the farms, covered bridges and drive through Green Mountain countryside to Manchester, finish with Equinox Mountain again.

This version would allow for a round trip loop from Boston, MA airport or Portland, ME airport.

The key to making the most of this shorter trip is to accept that you will be in the car driving a lot but that is where you will see most of the best scenery.

7 Day / One Week New England Fall Road Trip Itinerary

With a week, you can get more creative, include more places or take things slower. You have more flexibility but still not enough time to add a trip to Acadia, unless you really can’t miss it and don’t mind the driving.

Colors can change a noticeable amount in 7 days, so (if possible!) factor in starting your one week trip just before ‘peak’ begins.

Either of the 5 day examples above would work with 7 days by simply taking more time in certain spots. The alternative is to add in more places to visit. Let’s look at both:

Example 1 – Lake Winnipesaukee NH to Manchester VT

D2 – Kancamagus Highway : Take the awesome road trip slowly, stop at every attraction and stay in Loon Mountain or Lincoln.

D3 – Franconia Notch and Stowe : Hike Flume Gorge and Artists Bluff before driving to Stowe to photograph the church. Hike the waterfall trails and see Smugglers Notch. Stay in Stowe.

D4 – Burlington and Lake Placid : Church Street and Burlington bike path, then drive to Lake Placid, get stuck into the best bits of Lake Placid and spend the night there.

D5 – Lake Placid and Woodstock : Spend the morning in Lake Placid and drive to Woodstock later in the day. Hike to Mount Tom for amazing views over Woodstock. Stay in Woodstock.

D6 – Woodstock : Sunrise at Sleepy Hollow Farm, Jenne Road Farm, visit the nearby covered bridges and relax in town. Drive to Manchester later in the day to stay over.

D7 – Manchester : Hildene, Manchester old town and stunning Green Mountain country roads, finish at Equinox Mountain.

This variation could begin and end at either Boston, MA or Portland, ME as in the itinerary above. It just gives you more downtime and time to fully explore the places you will visit.

Example 2 – Manchester VT to Lake Winnipesaukee NH

D1 – Manchester : Drive from Boston airport to Manchester, spend the day at Hildene, Equinox Mountain and exploring the town. Stay in Manchester.

D2 – Woodstock : See the best of Woodstock and spend the night.

D3 – Stowe : Hit the top highlights in Stowe and stay there for the night.

D4 – Mount Washington : Take the cog train, drive to the summit or even take on the hike. Sleep in North Conway.

D5 – Kancamagus Highway : Spend a full day on The Kanc. Sleep in Loon Mountain or Lincoln.

D6 – Franconia Notch : Hike Flume Gorge and Artists Bluff but drive to Lake Winnipesaukee later to spend the night.

D7 – Lake Winnipesaukee : Spend the last day around the lake, cruising, hiking or relaxing.

This loop direction was reversed to give an idea about how you could make it work in a clockwise route. Again this would be starting and ending in Boston or Portland, with JFK or Newark as alternative options.

Instead of driving out to Lake Placid, you could stick to Vermont and New Hampshire, which is where the very best colors are found.

10 Day New England Fall Road Trip Itinerary

With a full 10 days to spend on your New England fall road trip, you can either max out your itinerary and see all of the best bits or choose to spend more time in fewer places.

Personally, we’re the max out itinerary type and we would definitely include Acadia National Park in our 10 days. It adds in some serious driving time but the journey there is picturesque, rural and most importantly colorful.

Here’s one way you can include each of the places mentioned in this list, including Acadia National Park (this is the way we drove but we spent 14 days doing this route with other non-fall foliage places included in our itinerary):

Example 1 – Lake Placid, NY to Manchester, VT via Acadia National Park, ME

D1 – Lake Placid : Spend the day hiking and surrounded by gorgeous colors. Sleep Lake Placid.

D2 – Burlington : Full day exploring town and cycle the entire bike path to Grand Isle. Stay in or near Burlington.

D3 – Stowe : Smugglers Notch, Mountain Resort, Mt Mansfield and church in town. Stay in Stowe.

D4 – Franconia and Kancamagus Highway : Hike Artists Bluff and Flume Gorge, drive The Kanc and sleep in North Conway.

D5 – Mt Washington and drive to Acadia : Drive to the summit or take the cog train before driving US-2 all the way to Acadia. Sleep in Bar Harbor.

D6 – Acadia : Sunrise Cadillac Mountain, Hike Acadia Mountain and Beech Mountain, sunset at Bass Harbor Head Lighthouse. Stay in Bar Harbor.

D7 – Acadia : Sunrise Schoodic Point, Hike Beehive Trail and Precipice Trail, Walk around Jordan Pond, Great Ocean Path and carriage roads by bike to see the best fall colors. Final night in Bar Harbor.

D8 – Lake Winnipesaukee : Final morning in Acadia, long drive to Wolfeboro and explore Lake Winnipesaukee.

D9 – Woodstock : Photograph Sleepy Hollow and Jenne Road, hike to Mt Tom, see covered bridges.

D10 – Manchester : Hildene, Mount Equinox, nearby Bennington battle monument and covered bridges.

Tips For The 10 Day Itinerary

The only concern with this itinerary is the inclusion of Acadia National Park. It’s a 4 hour drive from Mt Washington to Acadia and 4 hours 20 minutes back from Acadia to Wolfeboro.

However, if you do have more time you can include stops on the way to and from Acadia to break up the longer drives. US-1 and US-2 are picturesque but slow going. If you’re pushed for time, take the less scenic but faster I-95 instead.

Alternatively, if you’re not so bothered by Acadia, plan to spend even more time in each of the other 9 places in this list. That would give you wiggle room in case of bad weather and plenty of time to relax.

Notice how the route starts furthest north and loops around Acadia then comes back further south?

That’s because with 10 days you should try to ‘follow’ the peak colors as they transition southwards over the first two weeks of October.

New England Fall Road Trip Map

Red Markers – Locations of the 10 best places to visit on a New England fall road trip itinerary.

Click or touch the map to activate.

Zoom in and out, move around the map of New England to find locations for the best places to visit in the area.

More From New England

• Best things to do in Burlington Vermont
• Best things to do in Woodstock Vermont
• Driving the Kancamagus Highway in fall
• How to visit Flume Gorge in New Hampshire
• The best things to do in Lake Placid New York
• The best things to do in Stowe Vermont
• Top things to do in Manchester Vermont
• Unmissable things to do in Acadia National Park

We hope this New England fall foliage road trip guide with itinerary ideas helps you plan the perfect leaf-peeping vacation!

Please let us know if you have any questions about New England or need any help planning your visit in the comments below.

Happy Travels,

Mark and Kristen

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Mark and Kristen Morgan are travel, hiking and photography experts. Over the last 6 years traveling full time, they have explored more than 40 countries and 30 US states.

Where Are Those Morgans has been featured in USA Today, Gestalten, Get Your Guide, CityPASS and Condé Nast Traveler along with various other publications. Read more about us .

29 thoughts on “New England Fall Road Trip Itinerary: 10 Stunning Stops”

I really appreciate your compressive guide to New England for travel in the Fall. We have enjoyed most of the areas you mention in years past and loved it. My sister is visiting from Australia at perfect Fall Foliage time so we’re planning to do your 10-day roadtrip this year. I was wondering if you have an App you prefer to use to plan each segment of the roadtrip. I used Roadtrippers earlier this year and found it good, but would welcome your suggestions for a roadtrip App. I plan to download your digital guide as well. Thank you and happy travels.

Hi Sharon, we’re happy to hear you will be visiting New England again and this time with your sister. If you are looking for alternatives to Roadtrippers you could check out Wanderlog which is another useful resource. But to be honest we don’t use any apps for our road trips except for the basic and free Google Maps app. We plot points for attractions, restaurants and hotels as we research before visiting a new place, and we plan ahead so we can really get organized. If you download our digital guide and go to the end, you will find a map we created that will open in your Google Maps app and it already contains the locations for top attractions, foliage photo spots, hikes, restaurants and hotels that we discuss throughout the guide. You can of course see more places but we have preloaded the map with the essential spots to visit around New England in fall. Have a fantastic trip!

@Mark and Kristen Morgan, Thank you so very much for your advice. I downloaded the digital guide to use. So looking forward to this trip and having your guide to get organized makes this a lot less daunting. Keep up the great work and happy traveling.

Hi Sharon, Visiting New England in fall is an amazing trip and you will have a wonderful time! Thanks so much for taking the time to leave a nice comment and downloading our guide. Just let us know if you have any specific questions as we get closer to fall season 🙂

@Mark and Kristen Morgan, I have accommodations booked from Lake Placid to Woodstock. Since we want to add a couple of nights in Boston to walk the Freedom Trail and visit the Boston Tea Party site, would you recommend skipping Manchester, Vermont and going directly to Boston from Woodstock. Or, would we be missing out if we skip Manchester. Appreciate your advice.

Hi Sharon, you will have covered almost all of the best fall spots between Lake Placid and Woodstock. We like Manchester but it isn’t going to ruin your trip if you skip it, especially if you really want to see more of Boston. After 10 days or so you will have had your fill of fall colors anyway, so Boston will be a welcome change of scenery and pace. Have a fantastic time!

I would love a copy of the book as well, to use as we travel Thank you for a wealth of information!

Wow, amazing information, thank you. Have you written it in book form by any chance? I would love to drive with the book on hand for reference.

Hi Helen, you have asked at just the right time. We are currently in the process of creating a digital guidebook filled with key information and itinerary ideas for the New England fall road trip. It will be ready within the next week or so and we will email you once it is live. You will be able to either keep it on your smartphone or print it if you prefer to have a paper copy.

@Mark and Kristen Morgan, I’m using this article to plan our New England fall leaves trip and would also be interested in a copy of your digital guidebook, please. The information you provide is outstanding — thank you! ~ Carol

Thank you, Carol! We’re happy to hear you are planning a New England trip this fall. You can follow this link to see more details about our digital guidebook. If you do purchase the guidebook, remember to open up the map on page 45 when you are in each place to see the best hikes, foliage spots, attractions, restaurants and hotels. And if you have any specific questions, feel free to ask away. Have a fantastic trip!

Hello! What a wonderful site you have given us :). Question…do any of the New England fall road trips include the Berkshires? I would love to include a quick visit to The Mount/Edith Wharton’s home. Thanks, Jo

Thank you, Jo! Yes absolutely, you could easily add The Mount / Edith Wharton’s Home to the end of our 10 day New England fall road trip itinerary because it is just 1 hour 30 minutes drive to the south of Manchester VT (which is the last stop in our guide), before heading back to the Boston / NY airports. It wouldn’t be much of a detour and if you are heading that way you might also want to consider including a short drive along scenic highway 2, also known as The Mohawk Trail. Have a fantastic trip later this year!

Hi There! We are flying into Portland, (Sept 23rd) Maine and flying out of Boston, Mass (October 2nd) We have about one full week for our Fall Foliage road trip. Knowing we arrive Portland and depart Boston, what would you map out for itinerary.

Part II question, I prefer staying at one hotel for a few days and taking day trips as opposed to staying one night in several places.

Would it be wise to stay 3 nights near Acadia Nat’l Park and then 3 nights in New Hampshire (near all of the Franconia State Park and Kancamagus Hwy ?

Hi Erin, yes staying 3 nights in Bar Harbor and then 3 nights somewhere near Franconia Notch sounds like the best idea if you would prefer to stay in one hotel for each part of your trip. You can easily visit the most popular fall foliage areas in VT and NH from Franconia. Depending on how much driving you want to do, you could split your days into Vermont and New Hampshire. So one day you do Stowe, Woodstock and Manchester (the driving in between is just as picturesque as the towns), then another day you do Mt Washington, Kancamagus, Artists Bluff and Flume Gorge (which are all much closer together). Then stop at Lake Winnipesaukee on the way down to Boston. Hopefully the peak colors will be in north / central VT and NH early Oct for your trip – have a great time!

Love your site! we are planning a a Fall Foliage trip for 2023 over our 34th Anniversary. thinking any where from 10 – 14 days from the last week in Sept. to the first week of Oct. We are thinking to end our trip in Boston for a few days. If I followed tour 10 day trip guide would it make sense to fly into Albany, NY and out of Boston. Or are we better off to make Boston a long weekend trip?

Hi Randy, thanks for getting in touch and we’re happy to hear you’re planning a trip to New England next year, congrats on the 34th! Absolutely, flying into Albany and out of Boston makes perfect sense. If you make your trip 14 days total, you can follow the 10 day itinerary in our guide and then spend 2 or 3 days in Boston at the end. Something to consider is whether or not you want to see Acadia NP, it is a stunning place but it’s a long way out from the rest of New England’s top foliage spots. If you don’t include Acadia, you can spend longer in the fall color hotspots of Stowe, Woodstock and Manchester in VT, plus Franconia Notch, Kancamagus Highway and Lake Winnipesaukee in NH. Let us know if you have any more questions and best of luck with planning!

We are planning a trip to Maine in the fall of 2023 for our 40th anniversary for a total of 7 days. We would be interested in mainly leaf peeping,Arcadia NP, sight seeing/boat tours, driving the back roads and easy hikes. I really like the coast. Now that I have run across this post, I am rethinking our trip. What city should we fly into? Do you recommend spending 2 days in Arcadia NP? Should we hit some of the areas you mentioned in NH? I don’t think we have time to do your whole itinerary in 7 days. Your thoughts?

Hi Randi, glad to hear you have a trip planned to Maine for your 40th anniversary – congrats! Honestly, 7 days isn’t enough time to be rushing around New England trying to cram in everything. If you like the coast and you want to do Acadia, why not fly into Portland in Maine and slowly drive up to Bar Harbor via the back roads? Acadia is great but it is touristy and expensive, plus you won’t get the best fall colors (when compared to NH or VT). Boothbay Harbor is a nice place to stop between Portland and Bar Harbor, and you can do whale watching tours right out of the small town. If Portland doesn’t work for flight times or prices, Boston will be your best bet. Let us know if you need any more help before you travel next year.

Hi. I’m glad I found this. We are planning our 50th Anniversary to see Vermont and Maine in late September. Is it possible to stay in one place and drive to see the sights? We don’t want to keep changing hotels. This is a lifetime dream for us. Thank you.

Hi Jan, congrats on your 50th anniversary! Without knowing exactly which places in Vermont and Maine you want to see, it is possible to stay in one place but that would mean quite a lot of time spent in the car. If you have a 50/50 split, maybe stay somewhere in New Hampshire in the middle? Or if you plan to spend more time in VT, stay somewhere just inside VT near the NH border? Somewhere near Franconia NH might be a good fit so you are central to most of the fall hot spots and far enough North to see peak colors at the end of September. Have a great time!

Great article! While planning and researching for our New England Fall Foliage Adventure we saw right away that trying to predict “peak” conditions was a difficult proposition, at best. With that in mind and because we have a bit of time on our hands we decided our adventure would be from mid September to mid October 2022. We have booked all of our accommodations and now it’s all about deeply researching the areas and filling in the days. Finding your well written and in depth blog helped confirm our research was spot on and added to our happiness that we are actually going to pull this off. Plus, now we have an excellent study guide to boot! Bring on the trails, the mountains, the breweries, the lobster, cheese, cider donuts, Octoberfests and even the rain! Thank YOU and keep up the fantastic and insightful work!

Hi Jeff, thanks for getting in touch and we are so happy to hear you have planned a full month up in New England! Your list of activities is spot on – hiking, scenery, fall colors, food and beer … recipe for a perfect trip! Good luck filling in the days and hopefully you’ll get optimal weather conditions leading into the peak, just remember to keep an eye on the peak fall colors tracker when you are on site in New England. Have a wonderful trip!

Hello! This post is really very useful! We are planning to go to New England from September 30th to October 8th (we have already booked our flight from Italy). Since we would like to spend a couple of days in Boston too, do you recommend to begin with Boston and then start our road trip or to do the other way round? We would very glad if you could give us more details! Thanks a lot!

Hi Simonetta, thanks for getting in touch and we’re happy to hear you will be visiting New England this fall! This is a tough question because nobody can predict when “peak” fall colors will be in each part of New England. You can keep an eye on a live peak foliage tracker and book everything last minute, but that is risky as accommodation will book up. So, we would suggest starting with Boston and then driving up as far North as you will go on your trip (ie Stowe in VT or Franconia in NH) and then working down South to follow the peak. Please let us know if you have any more questions and you might even see us up there somewhere this year! Have a great time 🙂

I’m so happy to have found your blog post. I know how much time and effort goes into planning these type of trips, so I appreciate you writing about it and sharing it. We are looking at doing a mix of rural/city for both NH, VT, and ME. Looking closer to a 10 day trip and flexible on the dates. Would you say the hikes are fairly easy, medium, or difficult? Do you think looking into Air BNB’s out there would be better vs. hotels?

Hi Ani, thanks for getting in touch and we’re glad to hear you have a trip planned for VT, NH and ME. There are countless hikes spanning the difficulty range on this road trip route, so you do have a lot of flexibility over how long you want to spend hiking and how hard the trails are. Artists Bluff is short but has a steep climb, so we would say it is moderate but well worth it. Flume Gorge is easy and shouldn’t be missed. Acadia (if you make it that far) has a host of easy through hard hikes. Lake Winnipesaukee has plenty of hikes to suit all. If you’re looking for hard hikes take on Mt Washington or Mt Mansfield, tallest in NH and VT. You’ll likely only be spending one night or a maximum of 2 at any given place so we would say go for hotels. AirBnB’s are great for uniqueness and meeting people but for one night they are always more expensive with cleaning fees / service fees etc. By all means check prices and see if you can find any good deals or special places but we will be sticking to hotels ourselves the next time we are in New England. Let us know if you need any more help and have a fantastic trip!

Great information, love your post! We have never been to New England and would like to go see the fall colors in late Sept. or Oct. We also want to spend some time in Boston and Cape area. We are flexible on dates and number of days in itinerary. We would be interested in some hikes. After looking at you post I’m thinking Vermont and New Hampshire might work after seeing Boston. Can you help with an itinerary? We would be flying from San Diego, CA. Would appreciate any information! Thank You!

Thanks for getting in touch, Marilen – we’ll respond through email so we can provide more information.

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How to Plan a U.S. History Road Trip (and make it fun!)

S ometime around middle school, most students in the United States will study U.S. history. This is the perfect time to plan a U.S. History road trip through the Mid-Atlantic and Northeast to visit many of the main historic sites that are so relevant to the founding of our country.

We have found through our travels that seeing a place in real life and walking in the steps of our Founding Fathers works wonders to bring history to life. There is something about learning (or relearning) the history in those places that makes everything click into place, stick in the memory better, and allows kids to see the bigger picture.

Of course, there is so much history to cover across the country, but for this itinerary, I would stick to the destinations related to our Colonial History and Revolutionary War on this northeast road trip.

Later, you can tackle other themes like a Civil Rights road trip , Trail of Tears or Oklahoma road trip , Lewis & Clark, etc.

On this US History road trip itinerary, you can squeeze everything into about two weeks, but if you have extra time you can add in some side trips and some fun stops along the way.

Northeast Road Trip Itinerary

I have started this road trip in Virginia, to explore some very early Colonial History, and worked our way up to Boston, but you can certainly take this road trip in reverse. To save time, I would recommend flying into Norfolk International Airport (Breeze Airlines offers some affordable flights into this airport.)

However, if that is too cost prohibitive, you can start in Washington D.C. and take a slightly different route. But to minimize driving and backtracking, I would suggest the following order: Williamsburg/Jamestown, Washington D.C., Baltimore, Philadelphia, New York, and Boston.

Map created with Google My Maps.

Williamsburg (2 days)

Note: This post contains affiliate links. If you click a link and make a purchase, I may receive a small commission.

It is approximately one hour from the Norfolk International Airport to Williamsburg. Along the way, you could always stop in historic Hampton, VA and visit the Virginia Air & Space Center or the Virginia Living Museum in Newport News. But if you have limited time and want to stay focused, head right to Williamsburg.

You can see Colonial Williamsburg in a day , but to fully enjoy it, you really want to give it two. There is so much to see and take in from troop parades to historic reenactments. You can also add on experiences like a carriage ride, ghost tour, or theater performance.

Side trip idea: If you have extra time, take a day to enjoy Busch Gardens amusement park or the Watercountry USA water park.

Where to Stay: I would recommend staying at the Woodlands Hotel & Suites in Colonial Williamsburg.

Jamestown & Yorktown (1-2 days)

Technically, if you want to follow history chronologically, you would visit Jamestown first, then Williamsburg, then Yorktown — but who needs to be fussy? Jamestown is about 15 minutes from Colonial Williamsburg and Yorktown is about 20 minutes in the other direction but if you are pressed for time, you could visit both in a day or spread them out and visit one a day, keeping your home base at the Woodlands in Williamsburg.

There are actually two sites to visit in Jamestown. There is Historic Jamestowne, which is the actual site of the original fort settled by Captain John Smith and some of the first European settlers. It is an actual archeological dig and while interesting, there is much more to see and do at Jamestown Settlement down the road. Confused? I was too so I wrote a post describing the differences between Historic Jamestowne vs. Jamestown Settlement .

Any Hamilton fan knows the importance of the Battle of Yorktown. The American Revolution Museum at Yorktown is a living history museum complete with galleries, films, and interactive exhibits. Here you can learn about the twilight of the Colonial period and the dawn of the United States. The Siege of Yorktown film tells the story of that decisive battle. Meanwhile, outdoor living history areas incorporate artillery demonstrations and drill reenactments.

It is easy to spend at least a half a day at each, so if you have the time, you may want to visit one a day and spend the afternoon relaxing.

Washington DC (3 days)

It is a two and one-half hour drive from Williamsburg up to Washington D.C.. After two family trips, we still have so much that we haven’t seen. Some of the must-dos for first-time visitors include: visiting the National Mall and Monuments (the Monuments are especially beautiful and peaceful to visit at night), Smithsonian National Museum of American History , National Museum of African American History and Culture (make sure you book tickets ahead), and the National Archives (to see the original Declaration of Independence.)

Other kid favorites include the National Air and Space Museum (and the excellent annex outside of D.C.), the Museum of Natural History (for those Night at the Museum fans), and the International Spy Museum .

Of course there is so much to see in the Capital that you could spend a week and still have more to see so don’t rush it, give yourselves at least three days in Washington D.C. Intersperse museums with bike tours through the Tidal Basin, walks through the monuments, and time playing on the National Mall.

Also keep in mind that if you want to visit the White House, you need to arrange it through your Congressman/woman at least a few months in advance and follow strict security clearances.

Where to Stay: There are many hotel options, with some of the affordable ones located just outside the city. Luckily the D.C. Metro is easy to use and an affordable way of getting around. If you do want to stay in walking distance to sites, we enjoyed our stay at The Darcy (a Curio by Hilton Property) and got a great deal!

Baltimore (1-2 days)

From Washington D.C., it is just an hour drive up to Baltimore. While there are not as many historic sites to see in Baltimore, I just love this city so much that I need to include a brief stay on this road trip itinerary. It can also make for a nice break from museums.

A visit to the National Aquarium is a must, but I’d recommend buying timed-entry tickets online in advance to save time waiting in line. You will still need at least half day at the Aquarium. Then there is so much else to do in the Inner Harbor from the Science Museum, to pedal boats, and historic ships.

You can also take a water taxi over to Fort McHenry.  The defense of Fort McHenry in the Battle of Baltimore inspired Francis Scott Key to write the Star Spangled Banner .

If you have time, be sure to explore the African American history of Baltimore . Whatever you do, don’t miss breakfast at Miss Shirley’s.

Where to Stay: Twice we have stayed at the Hilton Baltimore and I love the location. It is within easy walking distance to the Inner Harbor and right behind the Camden Yards baseball park so you can hang out on the conference level floor and watch the game (or book a room overlooking the stadium.)

Philadelphia (2 days)

Every US History road trip has to include a trip to Philadelphia. What better place to soak in our early U.S. history than where the Declaration of Independence was signed and the U.S. Constitution was penned?

Start off at Independence Hall . Tour tickets should be booked in advance. Here you can be in the “room where it happened.”

I have some other tips for touring historical Philadelphia because there is so much to see and do in the City of Brotherly Love. We especially loved the National Constitution Center , which did a great job describing the challenges facing our early nation and the hard work it took to put the Constitution together. It helped explain some of the compromises the delegates made and how some decisions, like not abolishing slavery, impacted the country for decades to come (and the impacts are still felt today.)

Don’t miss the Liberty Bell, but the lines can be long in the morning, so you are better off visiting late in the day or just viewing it from outside the glass building where it is housed. Personally, I think the Betsy Ross House could be skipped, but we loved the National Museum of American Jewish History .

For lunch, walk over to the Reading Terminal Market, where you will have your choice of treats from cheesesteaks, to pretzels, and funnel cake.

Side trip ideas : If you have time, schedule a side trip to take a dip into Civil War history (which is a great follow up after visiting Philadelphia.) I would recommend a scenic drive through Pennsylvania Dutch Country and spending two of days in Gettysburg and then visit the National Civil War Museum in Harrisburg, PA. We were really blown away by how much we loved Gettysburg and how impactful it was.

But if the kids are getting antsy by this point, plan a day in Hershey , the “sweetest place on earth” and home to Hersheypark amusement park and Hershey’s Chocolate World. On the drive back east, you can stop at Valley Forge National Park and get a little more Revolutionary War history.

Where to Stay: Try to stay in the historic city center to make everything very accessible. The Kimpton Hotel Monaco Philadelphia is the perfect location. I’ve stayed here twice and really like this hotel and location.

New York (2 days)

It is only two hours from Philadelphia from New York City, not accounting for the inevitable traffic. The first choice is choosing which neighborhood to use as your home base. If you are focused on history, I would recommend staying in Lower Manhattan. Otherwise, Midtown or Times Square is a good central location.

New York can be overwhelming for visitors so I usually recommend knocking off just one or two neighborhoods per visit. From Lower Manhattan you can visit the 9/11 Memorial and enjoy some free time in Battery Park. It is also a good jumping off point for visits to the Statue of Liberty and Ellis Island (if you want to learn some more recent U.S. history and trace the immigration routes of ancestors.)

However, for history buffs, the ultimate achievement in NYC would be to score tickets to see Hamilton on Broadway. Especially since we can credit this amazing show for getting so many kids interested in this period of history.

Even if you can’t get tickets (and I hope you can, it is such an amazing show!!), you can still take a Hamilton walking tour to see Alexander Hamilton’s New York. There is more history to explore in Lower Manhattan from the Federal Building to specialty attractions like the Tenement Museum.

If this is your first trip to Manhattan, you will likely also want to take the subway up to Times Square for some shopping or people watching. See my recommendations on the best things to do in NYC with kids .

With more time, you can venture into Upper Manhattan and Central Park. Two of my favorite museums are the American Museum of Natural History on the Upper West Side, and the Metropolitan Museum of Art on the Upper East Side.

Make sure you get a view of New York from above at the Freedom Tower, Empire State Building, or Top of the Rock in Rockefeller Center. If you are visiting many of these attractions, be sure to invest in the New York CityPASS to save money on admission fees (and get to skip some lines too!)

Side trip idea: If you have time to spare along the way to the next stop, follow my New York to Boston road trip itinerary .

Where to Stay: On our weekends in NYC, we have enjoyed staying at the Millennium Downtown , right near the World Trade Center and 9/11 Memorial.

Boston (2 days)

It is time to wrap up your trip with a four hour drive up to Boston. Along the way, you may want to plan a stop in Mystic, Connecticut . Still known for its Mystic Pizza, it is also the home of the Mystic Seaport. This maritime living history museum is a lot like Williamsburg, but from a slightly different era.

Once you arrive in Boston, I think making the waterfront area your home base is great for exploring. If you want to explore many of Boston’s top attractions, I’d recommend investing in a Boston CityPASS .

If you are interested in history, I would make the first stop a visit to the Boston Tea Party Ships and Museum . Here you will learn about the lead up to the Boston Tea Party to understand why the rebels threw all that tea into the sea. Then you can step aboard a replica ship and toss a bale over the side yourself! Afterwards, have tea in the tea room upstairs.

This is very close to both the Boston Children’s Museum and the New England Aquarium, which can balance out your visit. If the weather is nice, I also enjoy a harbor cruise (part of the Boston CityPASS) or you can take a ferry over to some of the harbor islands for a few hours.

Two other ways to explore the history of Boston (and the USA), would be on a walking tour of the Freedom Trail. You can do this self-guided, and spend time at different stops along the way, or taking a guided tour from a costumed docent to get the full story and significance behind each location.

The other fun way to explore is with a duck boat tour. These amphibian vehicles start off on land with a guided tour through the city and then splash into the Charles River for the “boat” portion of the tour. If you haven’t done one of these in another city, the novelty is super fun.

See more tips for visiting Boston with teens . SaveSaveSaveSaveSaveSave SaveSaveSaveSave SaveSave SaveSave SaveSaveSaveSave SaveSave SaveSaveSaveSave SaveSave

Where to Stay: We love both the Boston Harbor Hotel and the Intercontinental Boston .

That concludes the U.S. History road trip through the Northeast! There is so much to see, even more to learn, and plenty of fun to be had along the way. I hope you feel inspired to take your kids on a history-filled road trip.

The post How to Plan a U.S. History Road Trip (and make it fun!) appeared first on We3Travel .

The Best One Week Fall Foliage Itinerary for New England (Plus More Options!)

Here’s my guide to the best one week fall foliage itinerary in New England. New England is a classic American destination, the perfect place for a road trip.

As a born/bred/educated New England girl myself, I think New England is arguably one of the world’s most beautiful places in the fall.

Country roads wind through dense forests, stone walls, covered bridges, and idyllic farm properties.

Orange, red, and gold colors explode, rippling across the mountains. It’s the stuff of dreams.

If you want to escape the crowds and fall back into nature, I recommend adding a New England road trip to your USA bucket list .

Here’s my sample one week fall foliage itinerary, taking in the best fall colors in New England. I also give you plenty of options for extending your New England road trip if you have more vacation time.

In this 7 day New England itinerary, I spill the beans on the must see scenic spots in New England to experience the festival of colors, where to stay and eat, the top hikes, and photography inspiration.

You’ll start in the historic New England city of Boston and then head to the Berkshires, Vermont, and New Hampshire. I think New Hampshire and Vermont are the best place to see fall foliage, though I may be a tad biased.

If you have more than one week for your New England fall road trip, I give you some other options in Connecticut and Rhode Island to extend your time in this rural playground.

You can easily turn a 7 day fall foliage road trip into a 10-14 day itinerary for New England and stay longer in each place.

Overview Of One Week Fall Foliage Itinerary In New England

• Day 1 : Boston MA
• Day 2 : Berkshires MA
• Day 3 : Dixville Notch State Park NH
• Day 4 : Stowe Vermont
• Day 5 : Smugglers Notch NH
• Day 6 : White Moutains NH
• Day 7 : White Mountains NH
• Extra Time? Add Burlington Vermont, Connecticut, and Rhode Island

One Week Fall Foliage Itinerary For New England

Let’s begin the leaf peeping! Here’s where to go for fall foliage with one week in New England.

Day 1: Boston, Massachusetts

Begin your 7 day fall foliage road trip by flying (or driving) into Boston . Beautiful Boston Massachusetts is one of my favorite city in the United States. And fall is the perfect time to visit.

The country’s oldest city, Boston is steeped in American history. Boston played a pivotal role in the Revolutionary War.

Boston’s sometimes called the “hub of the world” or the “cradle of liberty.” The city was the source and inspiration for key ideas that shaped America.

READ : 3 Day Itinerary for Boston

Boston has a great foodie scene, wide open green spaces, quaint neighborhoods, and first rate museums. The prettiest neighborhoods, lit in colors in the fall, is Beacon Hill .

And Boston’s got loads of gorgeous fall foliage. To see the colors, head to Boston Public Garden, Boston Common, the Boston Esplanade along the Charles River, Beacon Hill, and Back Bay.

You can book a historic walking tour . The hop on hop off trolley bus takes you to Boston’s top attractions. You can also see check out the colors on a fall foliage lunch cruise .

After touring the city, pick up your rental car. Now, it’s time for some classic new England fall foliage. If you want to skip the big city altogether on this fall foliage trip, just add in one of my bonus destinations instead.

Where To Stay In Boston:

If you opt for downtown, I like the small  XV Beacon  or the  Klimpton Nine Zero Hotel. You could also splurge at the  Ritz Carlton  or the  Four Seasons .

The  Inn at St. Botolph , the  Lenox Hotel , and the  Hilton  in Back Bay are also nice options and central too.

If you can’t resist historic Beacon Hill, check out  The Boxer ,  Liberty , or the elegant  Whitney Hotel .

Where To Eat In Boston:

Barcelona Wine Bar, SVR, Yvonne’s, Beehive, Giacomo’s, Sarma, and o ya

Day 2: The Berkshires, Massachusetts

The Berkshires are a beautiful rural region of western Massachusetts that’s made up of 30 bucolic villages with some top tier leaf peeping, museums, and restaurants.

It’s a place of fall foliage glory In New England. The Berkshires are full of winding roads with rolling meadows and trees ablaze.

For some of the best fall foliage scenery in the Berkshires, take Route 7 and 8 from Great Barrington to North Adams (1:10 hours without stops).

You’ll go past storybook farms, wooden barns, and stone walls. And through the cute towns of Stockbridge, Lee, Lennox, and Pittsfield.

Stockbridge and Lenox are the two prettiest towns in the Berkshires, and make a great base for exploring. Stockbridge is home to the Norman Rockwell Museum and some of the Berkshires’ beautiful Gilded Age castle-cottages.

Lenox is home to The Mount , Edith Wharton’s home, more iconic properties, and fantastic restaurants.

The quaint town of North Adams is an arty town with an eye catching row of multi-colored Victorians called The Porches. If you’re in the mood for a museum after some leaf peeping, there are couple really good ones.

Try the Susan B. Anthony Birthplace Museum (in nearby Adams) or the spectacular Massachusetts Museum of Contemporary Art .

The Notch Road leads to Mt. Greylock State Reservation . You can drive up to the summit for Massachusetts’ highest viewing point.

There are plenty of marked hiking trails that start from the parking lot. Click here for the online trail map.

Then descend back down, exit the park, and take Route 7. This will take you to the small town of Lanesborough, where you’ll see pastures and horse farms. You can pick your own apples at Lakeview Orchard .

Near Route 7, you can also visit the home of Edith Wharton in Stockbridge. On your way back to North Adams, you can stop in Cheshire at the Whitney’s Farm Market.

Here’s my complete guide to the Berkshires .

Where To Stay In The Berkshires :

In Lenox, you can check out the intimate Wheatleigh resort fashioned as a Florentine palazzo. The Seven Hills Inn is a historic property on beautifully landscapes grounds with cottages.

In Stockbridge, you can stay at the historic Red Lion Inn or the Inn at Stockbridge , a charming B&B.

Where To Eat in the Berkshires:

Gramercy Bistro, Nuedel, Grazie, Mezze, Bistro Zinc, or The Portico at the Wheatleigh

Day 3: Dixville Notch State Park, New Hampshire

On day 3 of your 7 day fall foliage itinerary, get up early and drive 4.5 hours north to Dixville Notch State Park to venture into New Hampshire. Dixville Notch is a very small area. But what it lacks in size, it more than makes up for in unadulterated beauty.

The main road through Dixville features rolling hills and stunning scenery, including beautiful Lake Gloriette. Once there, hike the famed Table Rock Trail. You’ll need to pull off the shoulder and park on Route 26.

Table Rock Trail is a 1.5 mile out and back trail, with a relatively steep 700 feet climb. You’ll be rewarded with panoramic views over gorgeous Dixville Notch from above. If you’ve timed it right, you can even enjoy the sunset from your perch.

Another trail leaves from the parking lot of the Whittemore Family Cemetery on Google Maps. The trail winds its way through a vibrant forest, leading to a cute little bridge and stream. When you’re done hiking, head back to the nearby town of Colebrook for dinner and shut eye.

Where to stay : La Maison Bleue du Lac, Mohawk Cottages

Where to eat : Black Bear Tavern, Parsons Street, Wilderness

Day 4: Stowe, Vermont

Wake up early, grab some breakfast at Mostly Muffins in Colebrook. Then drive 2 hours west towards Stowe Vermont.

Along the way, you’ll pass scads of beautiful fall foliage and adorable rural towns, like the memorable Island Pond in Brighton.

Spend the day exploring the charming town. Where mountainous Stowe really shines is its hiking trails, with a range of options to suit every level of experience. Some take you to towering peaks, others end in waterfalls.

For beautiful fall views of Vermont’s Green Mountains, you can ride the ferry across Lake Champlain.

Another option is taking the Gondola Sky Ride at the Stowe Mountain Resort, for more beautiful aerial mountain views.

When you’re done hiking, snack on some apple cider donuts. Stowe also has a romantic and picture perfect downtown.

Its white steepled church is the focal point. Tiny Main Street is filled with boutiques, crafts stores, and antique shops. There are libraries, museums, theaters, and cultural organizations to keep your entertained.

Where To Stay In Stowe:

Stowe has some very nice hotels. The best option is the Topnotch Resort , with pools, a spa, and saunas. The Lodge at Spruce Peak is another good option. It’s at the base of Stowe Mountain and has awe inspiring views of the area’s lakes and peaks.

You can also check out the Trapp Family Lodge , with old world Austrian charm.

Where To Eat In Stowe :

Plate, Cliff House, Bistro at Ten Acres, Green Goddess Cafe

>> Click here to book a brewery tour in Stowe

Day 5: Smuggler’s Notch, Vermont

Day 5 of your one week New England fall foliage itinerary will be a busy one.

Wake up early and head 20+ minutes to the famed Smuggler’s Notch, detouring off Route 100 to Route 108. This magnificent area has a road that goes through a gap between two mountains (termed a “notch”).

Smuggler’s Notch is similar to Dixville Notch. But it’s even more stunning. The mountains on either side are massive.

There are many beautiful twists, hairpin turns, and massive boulders in the road. Unfortunately, there aren’t many places to stop and take photos. But there are two parking lots, at the Welcome Center and upper end of the notch.

From Smuggler’s Notch, drive south to Pomfret, Vermont. Take Cloudland Road south from Pomfret to Woodstock. You’ll drive along cute dirt roads lined with fall colors, rolling hills, and quaint farms.

If you’re hungry, stop in Woodstock for lunch at Mangalitsa or the Prince and the Pauper Restaurant.

Stop for a photography break at Sleepy Hollow Farm in Woodstock Vermont. It’s a great little stop that captures one of New England’s most photogenic farm properties now Instagram famous.

Sugarbush Farm is another local farm property that you can visit. Their maple syrup is famous.

Now, it’s time to head back to New Hampshire. At the base of the White Mountains, the town of Lincoln makes a good base for touring this area.

Then you don’t have to move every night. Lincoln is a creative foodie town, so plan on some fine dining there after your days of hiking and leaf peeping.

Where To Stay Near Lincoln: Omni Mt. Washington , Sugar Hill Inn , Riverwalk Resort at Loon Mountain , Red Sleigh Inn B&B

Where to eat : The Common Man, Gypsy Cafe, La Vista Italian Cuisine

Day 6: White Mountains, New Hamsphire

On day 6 of your one weeks fall foliage tour of New England, you’ll drive the sinuous Kancamagus Highway in the White Mountains.

It’s one of the most beautiful fall foliage drives in New Hampshire . You can drive the road with this self guided audio tour .

Be prepared to pump the brakes frequently. You’ll be dazzled by the incredibly epic roadside views on this 34 mile stretch of highway.

There a few places to pull over, providing great photo opportunities. Continue east until you hit the Rocky Gorge Parking Lot. Here, you can take a walk along the Swift River and get views of the beautiful Falls Pond.

From Rocky Gorge, backtrack a short distance to drive up Bear Notch Road. Bear Notch features a scenic drive along a mountainside and more roadside pullouts for gorgeous photo opportunities.

At the end of Bear Notch Road, drive north to Crawford Notch State Park .

Here, you can explore the backroads and revel in the beautiful fall colors. If you’d like to do some hiking, there are 35 hiking trails of varying difficulty.

The best hike in this area is the Mount Willard Trail . It’s a relatively steep, but short, 3.2 mile out and back hike to a clifftop vista overlooking Crawford Notch. The views are surreal.

Next, continue driving north where you can detour to the Mt Washington Cog Railway . Here, you can ride a historic train to the summit of Mt. Washington.

The mountain is the tallest one in the northeastern United States at 6,289 feet. At night, head back to your base in Lincoln.

Day 7: White Mountains | Franconia Notch State Park, New Hampshire

On day 7 of your New England fall foliage itinerary, you’ll head to Franconia Notch State Park. The park is a lovely spot nestled in the White Mountains, just 7 minutes from Lincoln.

Start your day with a sunrise hike up to Artist’s Bluff . This is a short 1.4 mile long loop trail up to a hilltop overlooking Echo Lake. The fall foliage here is simply breathtaking.

Continue on to Flume Gorge . This is one of the best stops on a New England road trip. The natural chasm stretches 800 feet along the base of Mt. Liberty.

A boardwalk provides a relatively easy 2 mile loop hike. Waterfalls, streams, and covered bridges keep the eyes riveted the entire way.

You can also be whisked away on the 80 person Canon Mountain Aerial Tramway , which takes you to the top of majestic Cannon Mountain for an “oh wow” view. Cannon Cliff is the northeast’s largest vertical rock face. Trails meander on the mountain.

You can also hike the Falling Waters Trail to beautiful waterfalls. Or bike or hike the 8.7 mile Franconia Notch Recreation Path.

The paved trail offer spectacular views of the White Mountains and access to Echo Lake. More adventurous travelers should pull in at Loon Mountain and zipline 700 feet across the Pemigewasset River.

Where to eat : Polly’s Pancake Parlor, Lovette’s Inn & Restaurant

Extra Time On Your One Week New England Road Trip?

It may be time to head back to Boston or home after your one week New England fall foliage road trip.

But if you have extra time on your hands, there are several places you can easily add to create a longer New England fall foliage itinerary.

1. Burlington Vermont

While you’re in Vermont, after Stowe, add a day in the lovely town of Burlington. As the largest town in a state of small hamlets, Burlington has developed a wonderful art scene.

To some, Burlington is akin to a mini Seattle — a politically and socially progressive enclave of college students, regional power brokers, and creative minds.

The city’s popular waterfront bike path includes miles of paths, many along Lake Champlain. Stop at Ethan Allen Park, with a 40 foot tower providing mountain views.

If you’re a foodie, Burlington will suit. It outshines much of the US with a bounty of locally grown food. Farm to table eating is a well established tradition. There’s even excellent street food at Farmers and Foragers Food Truck.

Where to stay : Willard Street Inn, Made INN Vermont

Where to eat : Bleu Northeast Seafood, Hen of the Wood, Juniper

2. Connecticut

If you want to venture south of Boston, Rhode Island and Connecticut also offer excellent fall foliage drives, with rolling foothills ablaze in color.

The best fall drive in Connecticut is the tree-lined State Route 169. This two lane scenic road connects picture perfect towns in a still rural corner of the state, often called New England’s “Last Green Valley.”

Along this relaxing and uncrowded drive, you’ll pass classic churches, orchards, stone walls, and 19th century homes. The pink neo-Gothic  Roseland Cottage operates as a museum.

It’s open for tours June through mid-October. For a break, stop at Mrs. Bridge’s Pantry for some tea and scones.

Another popular fall drive in Connecticut is from Milford to Litchfield. Along the way, you can stop at Hunt Hill Farm, with a gallery, shop, and cafe.

Continue to New Preston, where can you do some antique shopping at Dawn Hill Antiques . Then take the 8 mile drive around Lake Waramaug. In fall, it’s encircled with red maples, rusty oaks, and yellow birches.

Where to stay : Winvian, Grace Mayflower Inn & Spa, Inn at Stonington

Where to eat : Arethusa Farm, Schoolhouse at Cannondale

3. Rhode Island

The state of Rhode Island is the home of the red maple, which turns a glorious gold, purple, and scarlet come fall.

Start your tour of tiny Rhode Island in the amazing town of Providence. Providence combines big city sophistication with small town charm, vibrant culture with hot restaurants. Here’s may one day itinerary for Providence .

For leaf peeping in Providence, the tree lined vista from Prospect Terrace is stunning. There are beautiful trees along the downtown River Walk and on historic Benefit Street.

Drive north from Providence to the Diamond Hill Vineyards, which specializes in pinot noir. Then drive west to the village of Chepachet, where you’ll find Victorian homes and antique shops. A classic stop is at Brown & Hopkins Country Store .

Then hit the road and drive another 40 miles to Exeter. It’s lined with pristine hardwood forests with an abundance of red maple, white oak, elm, and poplar trees.

If time allows, you can continue on to the Colonial seaport town of Wickford, opening to Narragansett Bay.

Where to stay : Renaissance Providence , Graduate Providence

Where to eat : Gracie’s, Al Forno, Bacaro, Birch, Chez Pascal

When Is The Best Time To Take Fall Foliage Road Trip In New England?

The best time to see New England fall foliage is typically from mid September to late October. Even until early November in some places.

But it varies somewhat by state, fall coming earlier the further north you go. Some states have foliage trackers you can check to determine when peak fall foliage occurs: New Hampshire , Vermont , Massachusetts , and Connecticut .

I hope you’ve enjoyed my one week fall foliage itinerary in New England. You may enjoy these other United States travel guides and resources:

• 25 Prettiest Towns in New England
• Must See Places in the Berkshires MA
• 1 Week Road Trip for Vermont
• 10 Day Road Trip in Coastal Maine
• Flexible 10-14 Day Itinerary for Southwest US
• 10 Day Southern California Itinerary
• 21 Less Touristy Towns on the East Coast
• Best Art Towns on the East Coast
• Best Art Towns in California
• Famous Landmarks in Boston

If you’d like to take a fall foliage road trip in New England, pin it for later.

15 thoughts on “The Best One Week Fall Foliage Itinerary for New England (Plus More Options!)”

I like the sound and feel of your one week foliage road trip. When would you recommend doing that trip in the fall?

Thanks Eddie! Generally, mid September to late October is the best time.

Hi Leslie, do you do custom trip itineraries? We would like to fly into Maine and make a triangle Fall tour of Maine, NH and Vermont.

Thanks for your reply!

Hi Steve, I just don’t have time at the moment. I’m about to leave the country for travel again. But there is nothing better than fall in New England!

Thank you so much for this wonderful itinerary. It’s my first trip to the New England states. I am mapping things out now. Question: if I am driving to my final destination of Toronto, Canada, should I drive in the reverse order and go from Boston to the White Mountains to Stowe to Dixvill Notch, etc….?

Yes, that makes sense to me. Enjoy your trip!

Hi. Thanks for your lovely articles and suggestions. We are going on a NE Cruise in September and have available 5 extra days after the cruise in the NE area, we will be driving from Boston. We do not want to move around every night, and after reading your article I am thinking of just going to the Berkshires (maybe Lenox) and Stowe, then touring around those areas in the time we have. My question is where would you spend more time, Berkshires or Stowe? We will do 2 nights at one, and 3 nights at the other.

Definitely the Berkshires. I have a whole article on what to do in the Berkshires, if you use the search bar. I think Stowe is a one day visit unless you’re skiing.

This is awesome information. Thanks for putting this all together. Where would you suggest to stay on Day 6 & 7 ? There are no suggested places to stay in the article. Thanks so much !

There are lots of places to stay in the White Mountains. I should probably update the article. The nicest place is the Omni Mount Washington. You can also check out the Mountain View Grand resort and the White Mountain Hotel and Resort. Or opt for booking an Air Bnb.

This was exactly what I needed! Flying into La Guardia from Texas next week. We are renting a a car and doing a 6-day tour of New England. We were planning to end in Boston so we can go from there back to the airport. Can you give me an idea of where to start with having only 5 nights? Thanks so much for sharing this great information with us newbies!

You could just reverse the order and start in the White Mountains, staying only 1 night there instead. Or you could skip the white mountains and start in Smuggler’s Notch, spending an extra day in the Berkshires. I have a Boston itinerary, if you want one: https://www.thegeographicalcure.com/post/the-perfect-3-day-itinerary-for-boston-massachusetts

Hi Leslie! We’re planning to take your New England car tour and will be driving from southwest OH. We may stay at the American side of Niagara Falls on our way to Boston. Can you offer any tips on lodging or restaurants at Niagara Falls? Thanks much!!

Sorry, no, I haven’t been there in decades. Enjoy your trip Don!

We will be able to complete 5 full of the days of your itinerary, starting and ending in Boston. (Landing in Boston Sunday night, touring Monday – Friday, flying out of Boston Saturday late afternoon).

Which 5 days would you most highly recommend we hit? We do like hiking, if that helps.

Thanks for your great post!

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Last Updated on July 4, 2023 by Leslie Livingston

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This Coastal Destination Is One of England's Best-kept Secrets — With Charming Villages, Historic Castles, and Delicious Seafood

Surprised to learn that England has great beaches? Visit Suffolk, in the northeast, and you'll understand why it's one of the country's most popular summer getaways.

Kate Maxwell is a freelance editor, writer, and author based in London. She is a contributing editor at Condé Nast Traveller (U.K.) and the former Europe editor for Condé Nast Traveler. Her work has also appeared in Travel + Leisure , Jetsetter , and more.

Michael Brooks/Alamy

Travelers in search of England’s classic seaside towns often head to Devon and Cornwall, southwest of London. But the popularity of those counties — particularly since more Brits snapped up second homes there during COVID — means bumper-to-bumper traffic in summer and restaurants booked out weeks in advance.

Many are now turning their attention to Suffolk , about two hours northeast of the capital, for its quiet beaches, meandering river walks, and elevated pubs and restaurants. Here’s how I spent a long weekend there recently. 

For a wild stretch of golden sand framed by crumbling cliffs, rather than the more popular Southwold Beach, I went to Covehithe, on the north coast of Suffolk. When I arrived mid-morning, it was nearly empty, except for a few families building sandcastles. I lingered for a while, watching a glossy black ibis tiptoeing toward the ocean, then drove to Walberswick, a seaside village on the river Blyth. After a lunch of crab linguine and an Adnams IPA at the Anchor , a pub with 10 guest rooms, I headed down the road to Thorington Theatre , a wooden amphitheater built inside a World War II bomb crater. Its popular summer calendar includes child-friendly Shakespeare and comedy acts.

Jemma Watts

From there, it was a short drive to Wilderness Reserve , an 8,000-acre estate with 27 individual lodgings, including cottages with one to six bedrooms and two sprawling manors, one with 13 bedrooms and one with 17. My one-bedroom thatched-roof cottage had its own swimming lake and hot tub, plus a sauna and a steam room. The sitting area had a dramatic brick chimney that corkscrewed from floor to ceiling. It was a chilly evening, so I ate my fish pie — freshly made and delivered to my door — in front of a crackling fire. 

After breakfast, I paddled around my private lake in a rowboat. Guests at Wilderness Reserve can also try clay shooting, paddleboarding, axe-throwing, and archery, so it’s tempting to stay put. (A Wilderness ranger even set up a target behind my cottage so I could test out my bow-and-arrow skills.) But this part of Suffolk is strong on art galleries, so that afternoon, I popped over to Yoxford to visit Rowe & Williams , which specializes in modern and contemporary works by local artists. I was drawn to a 1970s oil painting of Walberswick with a glittering Pointillist sea by Lionel Bulmer, who lived in Suffolk for several decades.

Aldeburgh, perhaps Suffolk’s best-known town, was my next stop. Its main road, High Street, is a parade of brightly colored Georgian cottages and stores like Aldeburgh Bookshop , which hosts a small literary festival each year. I browsed the titles by Suffolk authors, then took a windy walk along the beach, dodging kite flyers and seagulls swooping for stray morsels of fish and chips. 

Courtesy of The Suffolk

I had dinner at the Suffolk , a recently restored six-room inn where I also spent the night. The restaurant by George Pell — the man behind London’s legendary L’Escargot — began as a pop-up and opened permanently in 2022. My favorite dishes were the seaweed pappadums (inspired by the Indian snack) served with a dollop of oyster mayonnaise; crab in a brioche bun; and brill drenched in butter and capers. Spent from the day, I took my mille-feuille dessert upstairs to my room. The sound of the North Sea, which I could see from the window, lulled me to sleep.

Related: 13 Most Beautiful Castles in England

On my last day, I went to Snape Maltings , an arts complex near Aldeburgh that has become Suffolk’s cultural headquarters and hosts a well-known classical music festival each June. The brick buildings, which were used to malt barley in Victorian times, now house a concert hall, shops, and galleries. I found impressive sculpture, too: three of the bronze figures from Barbara Hepworth’s famous The Family of Man. (All nine of the figures were originally installed at the center in 1976.) 

For lunch, I headed to the Greyhound Inn , in the village of Pettistree. With Harry McKenzie, formerly of London’s storied River Café, at the stove, it’s also one of the county’s newest gastropub destinations. The River Café’s influence was clear in the daily menu; I ordered the light-as-air gougères (cheese puffs made with Gouda from neighboring Norfolk) and gnocchi with red mullet and crunchy breadcrumbs.

From left: Emma Croman; Courtesy of The Greyhound Inn

There was just enough time for a tour of Orford, a pretty town that was an important port and fishing village in the 12th century. These days, it’s best known for the pastries at Pump Street Bakery . I took my Eccles cakes (pastry filled with brandy-soaked currants) and walked along the Alde River, following the footpath to Orford Castle, which was built in the 1100s by King Henry II and recently restored. The tour guide regaled my group with colorful anecdotes, including a fable about a mute merman who was caught in a fishing net and imprisoned in the castle before escaping back to sea. 

The Merman of Orford is the emblem of Butley Orford Oysterage , a seafood restaurant just down the road from the castle. There, I had a dozen creamy oysters grown in the nearby Butley River. The meal seemed a fitting end to my weekend in Suffolk, a place connected by its beaches and marshes and rivers, each town perfectly unhurried and untethered.

A version of this story first appeared in the June 2024 issue of  Travel + Leisure  under the headline "Get Swept Away on the English Coast ."

Related Articles

How to Travel Stress-Free This Memorial Day Weekend

T his Memorial Day weekend, 43.8 million travelers are expected to hit the road to kick off the summer season.

Whether you’re staying local or spending the weekend out of town, be prepared for crowds. “It's going to be busy, no matter what you do,” says Christina Jelski, a senior editor with Northstar Travel Group’s Travel Weekly. “Leave early, give yourself plenty of wiggle room, and go in with the expectation that it's going to be crowded and delays [might] happen.”

Ahead of the busy weekend, TIME spoke to experts who shared their tips on how to make the most of the holiday no matter where you are.  

Think ahead

A little planning can go a long way when it comes to buying supplies for a weekend barbeque or booking passes for national parks— taking the time to get what you need ahead of the long weekend can save you a headache down the line. 

“Everyone talks about the mad rush at the airport and on the roads, but there's also a mad rush at the grocery stores,” says Erika Richter, VP of Communications & Marketing at the American Society of Travel Advisors. 

The same goes for your travel itinerary. Experts recommend creating a backup plan in case there are delays or cancellations. “If your flight’s delayed or canceled because during the holidays, you can't easily grab another flight,” says Karen Schaler, the founder of Travel Therapy. She recommends looking into alternative travel routes or backup flights in advance. “Do not count on the airlines to find you something over the holidays. If your flight is canceled, often [automatic booking] will rebook you for after the holidays,” she says.

Be creative with your travel plans

To beat the traffic, keep an eye out for destinations you can visit by train , especially if you live in the Northeast. “You could easily plan a quick weekend getaway by relying primarily on train service if you live somewhere that is well connected by train lines,” says Jelski, who notes that some hotels and resorts even provide shuttle or car service to pick you up from the station. 

It also helps to be open minded about where you plan to go—especially if you’re planning a last minute trip. “If you're looking to go last minute somewhere for the holidays, you're not going to pick the top 20 places that come to mind,” says Schaler. “If it came to your mind, it's going to come to somebody else's.”

Find ways to keep yourself entertained

Despite the excitement travel brings, a delayed flight or traffic jam can easily dampen the mood. To stave off boredom, Richter recommends packing games— like a pair of dice or a deck of cards—to pass the time while traveling. You can also create a shared playlist with your family or friends to listen to during your trip.“There’s something for everybody—and no one’s fighting over the music,” she says. 

Don’t forget to pack a portable charger. “If you're delayed or if you're just trying to recharge and you can't find one, you’re going to want to have your own,” says Schaler. 

Look around your neighborhood

You don’t have to travel far to have a good time, experts say. Many towns host free holiday parades, festivals, and concerts that help support the community. If you have kids, something as simple as making s’mores or bringing out glow sticks after dark can contribute to a fun weekend. “Even if you're not going anywhere, I would still think about what kind of memories you want to create,” says Richter.

It helps to ground a staycation in a specific theme, says Schaler, whether that be an outdoor day hiking local trails or a global food crawl through different cuisines. If you do decide to take a staycation, create boundaries—and stick to them. “Make sure you go all in,” Schaler says. “You can't be answering phone calls and doing a little work and then say, ‘This is my spa day.’”

More Must-Reads from TIME

• Javier Milei’s Radical Plan to Transform Argentina
• The New Face of Doctor Who
• How Private Donors Shape Birth-Control Choices
• What Happens if Trump Is Convicted ? Your Questions, Answered
• The Deadly Digital Frontiers at the Border
• Scientists Are Finding Out Just How Toxic Your Stuff Is
• The 31 Most Anticipated Movies of Summer 2024
• Want Weekly Recs on What to Watch, Read, and More? Sign Up for Worth Your Time

Write to Simmone Shah at [email protected]

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A Journey through the Malaysian Rainforest Aboard the Legendary Eastern & Oriental Express

By Arati Menon

I pried open the blinds, letting dawn’s filigreed light into the cabin. Outside my window, wild forest zoomed past. All night the train had barreled up the “jungle rails,” a historic set of tracks that spans the length of peninsular Malaysia, from its southernmost tip to its border with Thailand in the northeast. Those tracks would lead us to Taman Negara, one of the world’s oldest rainforests and the last refuge of the Malayan tiger.

I was one of 56 passengers, from as far as Texas, Romania, and New Zealand, who’d assembled the previous afternoon at Singapore ’s Woodlands station to experience the return of the Eastern & Oriental Express, A Belmond Train, Southeast Asia, four years after being shut down by the pandemic. Waving the sticky heat around with our tickets, we awaited our boarding call, combing the crowd for the likelihood of new friendships.

Belmond’s Eastern & Oriental Express returns to Southeast Asia with two new routes from Singapore through Malaysia.

There’d be plenty of time for both great conversation and long silence. Over three days the train would bear north on the eastern coast to Taman Negara, then backtrack and head up Malaysia’s more populated west coast to Penang , before looping back to Singapore. We’d pass forests, paddy fields, and townships while cosseted in the silken luxury that Belmond’s sleepers, like the Venice Simplon-Orient-Express , are renowned for. For its second coming the train has retained its trademark exterior green and gold, but its interiors have been carefully restyled. My cabin was bathed in peacock blues and jade greens, with vintage touches like brass lamps and fine marquetry. A velvet couch would turn into a bed at night; cherry wood paneling concealed a full bathroom. This was my private oasis—breakfast and high tea would arrive here, along with wake-up calls and turn-downs—and for my part, I’d sit by the large windows with the tasseled curtains and surrender to the views.

The cabins on the train (like the Pullman cabin, pictured above) have been restyled with rich velvets, Thai silks, and vintage touches like brass lamps and fine marquetry.

On our first evening the piano bar—resplendent in gold Thai silks, with tiger orchids blooming across the green carpet—was filled with laughter, the glug-glug-glug of Champagne pouring, and the tinkle of keys. An opening night special, magician Ming Da brandished a pack of cards and a broad grin for guests in floaty dresses and linen jackets. I met Andy and Chris, a young couple in tech from San Francisco, and Rob and Alan, brothers from Nova Scotia with unflagging pep. We toasted the start of the journey, then ate laksa bouillabaisse in the train’s glamorous dining cars as it trundled through the darkness.

About twice the size of Singapore, Taman Negara is the largest protected lowland rainforest in Malaysia. It’s the headliner of Belmond’s “Wild Malaysia” itinerary, which gives passengers special access to its diverse and vulnerable ecosystems. Accompanied by guides, we piled into jeeps and drove through pristine forest wreathed in mist, looking for signs of the dusky leaf monkey or barking deer. I knew better than to expect to see a tiger—the species is critically endangered here. An elevated walkway took us close to the canopies of trees, including the majestic Tualang, which have been undisturbed for millions of years. We waded in a river where Mahseer fish nibbled at our feet, and ate spicy karipaps and seri muka on its shaded bank. Illegal logging and poaching are ever-present threats in Taman Negara, but for a moment the babble of the river and the chattering of cicadas let us forget those concerns.

In the train's glamorous restaurant carriages, guests are treated to regionally-inspired fare such as Penang duck curry and laksa bouillabaisse.

Early morning wake-up calls are happily accompanied by breakfast in bed.

Daytime excursions such as this are designed to spotlight less-explored sides of Malaysia. On the second morning we rode a ferry to George Town, a colonial port on the island of Penang, where we twisted through its by-lanes by Vespa, exploring street murals, shop houses and artist ateliers. Other adventures were less planned: a longer-than-usual pit stop at the historic tin-mining town of Ipoh turned into a heritage walk, with train manager Wolfgang Eipeldauer leading a small group past stately colonial buildings and hip cafés with peeling paint and bright stools.

But perhaps the greatest pleasures came from finding a quiet corner and losing myself in the unfolding landscapes. The ride affords glimpses into the small towns of rural Malaysia, where a quarter of the country’s population live, with their candy-colored homes and tin-roofed stalls. Between the towns there are rice fields, limestone outcroppings, and repeat patterns of oil palms that stretch as far as the eye can see.

Daytime excursions include a visit to George Town's colorful alleys, traditional temples, and artist ateliers.

The observation carriage, with its wraparound windows, is the perfect spot to take in the shifting landscapes.

When I wanted company, the piano bar was a fulcrum of swinging social activity. There Kishen, the lead bartender, dipped into his arsenal of dehydrated herbs, grilled pineapple shrubs, and baobab jellies. “I’m not just making drinks,” he told me. “I’m giving you a piece of my heart.”

By Olivia Morelli

By Matt Ortile

By Jessica Puckett

By Juliet Kinsman

As the journey progressed, the passengers’ stories got more personal. Barbara, an older British lady, recounted the bucket-list adventures she’s gone on every year since emerging from a long coma 27 years ago. By the third day guests were sharing cigars and coffee on the observation deck and passing out tiaras and maracas for birthdays of fellow passengers.

The carousing reached its apogee on the final night. After a sumptuous meal that included Penang duck curry, a few of us returned to the bar, where the singer was belting out power pop hits. Chris and Andy ordered a round of nightcaps—pineapple-infused cognac sweetened with honey from the Tualang tree, which came out flaming—and then a couple more. “One more song,” we took turns shouting. We’d barely noticed when we arrived (or when we left) Kuala Lumpur; the bar car had turned into a rowdy sing-along. By morning we’d be back among Singapore’s bright lights and thrumming streets. But in this moment, we were a world away.

The piano bar is designed for lively sing-alongs.

A postprandial nightcap as the train trundles through the darkness.

What to know before you go

There are currently two routes offered on the Eastern & Oriental Express. The three-night Wild Malaysia itinerary departs from Singapore, traveling northeast through Malaysian countryside to Taman Negara National Park before heading back down and then up the Western coast of Malaysia to Penang and looping back to Singapore. On the Essence of Malaysia itinerary, which also runs for three nights, you travel from Singapore through Kuala Lumpur, Langkawi, and Penang, with excursions that allow for snorkeling and island exploration.

There are three levels of cabins available on Belmond's Eastern & Oriental Express. The Pullman Cabin in shades of orange and red is the narrowest and comes with two berths; the lower berth turns into a plush couch by day. The slightly larger State Cabin, bathed in peacock blues and greens, has twin beds—the couch turns into one, while the other pulls out from the wall by the window. The Presidential Suite offers the most space with a larger bathroom, a separate seating area, a mini bar, and additional storage. Each night, an indulgent turn-down service turns your cabins into bedrooms—look out for the thoughtful gifts on your pillow.

What to pack

You are allowed to bring approximately 60 lbs. of hand luggage with you on the train—and the recommendation is to bring soft luggage. Cabins come with a luggage rack and a narrow storage cupboard with a few hangers. If you have additional luggage with you, the team offers to safely store it for the duration of the train trip, but remember, it won't be accessible during the train journey, so ensure your medicines, wallet, passport, toiletries, and any important gadgets are packed in your hand luggage.

How to dress

For daytime excursions, pack cool, breathable cottons and linens, as well as comfortable shoes for walking and a hat for protection from what can be an unyielding sun. By evening, the vibe on the train turns more formal—think cocktail dresses and sandals for women and summer jackets and loafers or Oxfords for men. Still, there’s an ease to the atmosphere on board compared to some other luxury trains, even within the Belmond universe. Dinner jackets are recommended but far from insisted upon—an “unbuttoned luxury,” if you will, that suits both climate and landscape.

Recommended

Shangri-La Rasa Sayang, Penang

Four Seasons Hotel Kuala Lumpur

Asia Travel Guide

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