new england trips boston

New England Summer & Fall 8 Day Tour from USD $1695 #1 In Value

Dear Traveler, Welcome to a great vacation at an affordable price. Your New England tour is fully guided and includes all hotels, activities, and some meals. Happy Travels! Caravan

2024 Daily Tour Itinerary

Day 1 • boston, massachusetts, day 2 • plymouth rock, hyannis, day 3 • martha’s vineyard, day 4 • rhode island, connecticut, day 5 • norman rockwell, vermont, day 6 • white mountains, new hampshire, day 7 • portland, southern coast of maine, day 8 • maine to boston, fall foliage in new england, 2024 hotels, embassy suites logan airport, days 2, 3 • hyannis, cape cod, massachusetts, doubletree hilton hyannis, day 4 • mystic area, connecticut, mystic hilton, day 5 • mount snow, vermont, mount snow grand summit resort, the glen house, day 7 • southern coast of maine, anchorage by the sea resort, ogunquit, airport transfers, arrival transfers, departure transfers, passports & visas, weather & clothing, temperature °f (high/low) rainfall (inches), clothing tips, travel tips & faqs, are meals included, children on tour, family trips, my tour price does not include, my tour price includes, age of travelers on a caravan tour, forms of payment, many tours sell out each year, fully guided tours since 1952, size of tour group, a well-paced itinerary, caravan’s $129 travel protection, customer reviews.

"This was my dream vacation and along with my husband, best friend and her husband, I couldn’t have asked for a better time. Breakfasts were amazing, the hotels very nice clean and the scenery was just beautiful. The sights were awesome, more than I ever expected. The colors were perfect and the history was out of this world. Saw everything we hoped for plus more than was planned. The fall foliage was at the perfect time and was beautiful. I would definitely take another tour with Caravan. It was a lifetime experience. Everything I wanted to see. Thank you." Mr. & Mrs. S.B., Minot, North Dakota

"Beautiful, magnificent hotels. The views from the hotels in the mountains were breathtaking. The photo stops were great and offered all the marvelous views of each state. Sightseeing was awesome, so many things to see and do." Ms. N.K., Apopka, Florida

"Thoroughly enjoyed my first trip with Caravan Tours - will return for other trips! Enjoyed all the sightseeing opportunities and added ideas from our director, who was excellent and pointed out sites to see for pictures. Gave historical info, added stories, answered questions. Provided materials and maps and was always very polite, friendly and cheerful. We had sufficient time to enjoy the surroundings and take pictures. Enjoyed the variety of activities, films, displays. All the hotels were four to five star with clean comfortable beds and self controlled environments. Just a lovely time all around. Will share with friends." Mr. & Mrs. J.A., Tucson, Arizona

"Over the top! First time to New England and I really felt we covered so much, enough to suit everyone. I’m an artist and took so many pics, I’ll be painting from them for years to come. This was the first guided tour we had ever taken so we did not know what to expect. Tour was GREAT. We thought going in that would be lots of down (boring) time. Wrong. All the activities were well-planned and fun. Tour was set up to provide much to see. The time went by fast and colorfully. We were told by a couple that wasn’t on the tour who saw our Caravan luggage tags that we would have a great time and that Caravan does the best tours. SO TRUE! Thanks for a wonderful trip." Mr. & Mrs. E.L., Aurora, Colorado

"The Caravan value is unsurpassed. We would highly recommend this tour to anyone who has never traveled to New England states, loves history and beautiful scenery. We were fortunate to enjoy a late fall foliage. Photo stops abound on the multistate tour. We really enjoyed the history and beauty of the region. Our tour guide left no question unanswered. We loved the smaller boutique hotels and the condo with the fireplace." Mrs. C.D., Reisterstown, Maryland

"This was my first guided tour, and I feel like I hit the jackpot. Our director shared insights into history and was attentive to our needs. Our team worked together to offer us the best views and colors, even making some adjustments along the way. All our short stops were for rest and conveniences and beautiful photo opportunities. All our main activities were well-planned, with plenty of time to enjoy each stop, and the colors were breathtaking. I truly enjoyed this trip. I enjoyed meeting new people and our weather was spectacular. I will definitely recommend Caravan to others." Ms. F.L., Rusk, Texas

"Excellent. We learned so much more of our country’s history, and our TD was the best. Couldn’t have asked for better. We all laughed and had a great time. We were so pleased with everything we did. All the staff at each hotel were wonderful, and the seafood was terrific. So nice to not worry about our bags and rooms. Love your company and will tell everyone what a great time we had. You are the best!" Mr. & Mrs. S.M., Bayfield, Colorado

Why Travel with Caravan?

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Adventures in New England

A local's guide to savoring the history, culture, food and nature of the Northeast USA

19 Fabulous Day Trips from Boston

If you are planning a road trip from southern New England, Boston can be a perfect base as it is centrally located. You can get a hotel and then take many great day trips from Boston to experience the best that this area has to offer.

You will want to start by taking a few days to experience New England’s largest city’s feel. You can read my guide for One Day in Boston with Kids (still a good overview even for adults). Also, be sure to check out my list of hikes right around Boston .

Table of Contents

Short Day Trips from Boston

These day trips from Boston are around an hour’s drive from Boston.

Salem, Massachusetts

Witch City, USA, also has a fantastic art museum and Hawthorne’s House of the Seven Gables. Read on for how to spend a day in Salem. 

Fall River and New Bedford, Massachusetts

This center of fishing life in colonial New England is now predominately Portuguese. You can visit the New Bedford Whaling Museum, the church that was part of Herman Melville’s Moby-Dick inspiration, and the Lizzie Bordon House.  Read more about the area in Haunted New England.

Rockport, Massachusetts

Spend a day exploring this picture-perfect fishing village on the coast north of Boston.

Cape Cod, Massachusetts

There is a lot to explore on this peninsula south of Boston, but you can explore the upper Cape in one day from Boston. Most of my exploration of the Cape has been by bicycle.

Portland, Maine

This foodie town also has lighthouses and parks to explore. Check out 47 Cool Things to Do in Portland, Maine.

Providence, Rhode Island

The capital of Rhode Island has canals to stroll along, great restaurants, and art museums. Read on for The Best Things to Do in Providence.

Newport, Rhode Island

This colonial town on Aquidneck Island has excellent beaches, hiking, dining, and a lot of history. Explore A Local’s Guide to Newport.

Sutton, Massachusetts

Hike this trail along the base of the 75-foot rock Purgatory Chasm and get ice cream at the farm next door. Read more about a day at Purgatory Chasm.

Concord, Massachusetts

Concord was not only an important location in the American Revolution but also in American Literature. Walden Pond sits in Concord, as well as Louisa May Walcott’s home. Read my itinerary for one day in Concord, Massachusetts.

Plymouth, Massachusetts

Visit the recreation of the Native American and pilgrim colony following the landing at Plymouth Rock.

New Bedford, Massachusetts

Explore the colonial whaling capital of the world, located on the southern coast of Massachusetts. This area also has a large Portuguese population, a fort, and was a stop on the Underground Railroad.

Read about how to spend a day in New Bedford. 

Whole Day Trips from Boston

It will take about 2 hours to get to these full-day trips from Boston.

Martha’s Vineyard

Sand dunes, farms, Kennedy history, and gingerbread cottages, this island off the coast of Massachusetts will introduce you to the best New England has to offer. Read on for Things to Do in Martha’s Vineyard .

Woodstock, Vermont

Woodstock is sometimes known as the quintessential New England town. It is nestled in Vermont’s Green Mountains and alive with the state’s art culture. Plan your day with Things to Do in Woodstock, Vermont.

Northampton, Massachusetts

This arty town in northwest Massachusetts is the home of Smith College. Read on for how to spend a day in Northampton.

The Berkshires, Massachusetts

One of the most transcendent concerts you can experience will take place at Tanglewood in the rural mountains of western Massachusett. The Berkshires give ample opportunities for hiking, leaf-peeping, and exploring small New England towns.

New Hampshire’s White Mountains

Take a foliage drive or go waterfall hunting through the White Mountains.

Mystic, Connecticut

Explore the seaport at this colonial town on the Mystic River. Investigate more things to do in Mystic.

Mount Major, New Hampshire

The views from the peak of this half-day hike are incredible. You will see New Hampshire’s lakes and highest peak, Mount Washington, in the distance. Learn more about climbing Mount Major.

Shelburne Falls, Massachusetts

This village nestled in the Berkshire Mountains has the Bridge of Flowers, a waterfall, glacial potholes and an art-filled downtown. Read about how to spend a full day in Shelburne Falls.

Which day trips around Boston have you taken? Which are the highest on your list? Please let me know if you have any questions in the comments.

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12 thoughts on “19 Fabulous Day Trips from Boston”

I love this list! Boston is such a cool city and I love the idea of spending more time there and venturing out so this list is so helpful!

So many great day trip options from this city! Nice when there is that option, for travellers, it means you can extend your holiday. Make Boston your home base and see some of those smaller towns you have listed. I would love to see more of the nature, in New Hampshire, like Mount Major or Massachusetts with Martha’s Vineyard.

Such great day trip plans even a month of stay there will not suffice to experience it all! The short day trips really sound good and doable. I have not been to Boston yet, but hopefully I will some day with this helpful post! Great pic to go with the post.

Wow! So many things to do. It would really be worthwhile to make Boston a base for a week and do these trips to immerse yourself in the region.

Visiting the east coast has always been something i’ve wanted to do. I’ve seen Boston & DC but that’s about it! Rhode Island, Connecticut, Vermont, Main, I want to see them all!

Funny enough I’ve heard most of these day trips destinations from Boston although I don’t know their locations to Boston. I would like to visit most of them, but I think Fall be the best time?

Some of the locations are close enough for a day trip but would plan an early start in the day because even though they are close enough for a day trip, traffic can play a big factor especially during rush hours… planning a trip to the South Shore or Cape Cod offers only 2 travel lanes for most of the trip once you are on Route 3 which starts in Braintree which is about 9 miles south of Boston and the from Braintree to the beginning of the cape it’s about 45 miles or so… I mention this trip because I am very familiar with this section of MA and I live in Plymouth which is about 10 miles from Cape Cod… The Fall or Spring would be best as far as traffic to the cape but many places close down from Oct to Apr because many businesses depend on tourists during the Summer.

You are right about Boston traffic being a bugger. It is always best to consult Google traffic before leaving, start early or consider public transport. I love travelling in shoulder season.

While there’s still so much to see and do on my actual Boston list, I *did* take a day trip from Boston during one of my visits. We followed your recommendation to visit Providence, RI, and had a lovely day!

I just love the northeast and you’ve given me even more places to explore up there! Perfect fall long weekends!!!

Cape Cod, Massachusetts would be my #1 choice. Haven’t been since I was little and have such fond memories!

I have been to Boston several times now and even took a trip up to Maine & Connecticut once but I have been quite lax on visiting the other areas. For me, I really want to see more of the New England Coastal areas like Providence and I know Darcee would love to see Martha’s Vineyard!

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New England Tours & Trips from Boston

15 new england tours from boston with 611 reviews.

Explorer Family Sightseeing Historical +1

New England's Fall Foliage (Classic, 8 Days, Boston Airport And Post Trip Hotel Transfer)

Explorer Family Coach / Bus Sightseeing Historical +2

Classic Fall Foliage

"The tour itself was very well organized and accommodating to individual needs!" Robert, traveled in October 2022

Cape Cod & the Islands

"The food was great, the hotels were excellent and the choice of tour spots and stops were each unique and very interesting." Steve, traveled in September 2023

Boston Cape Cod and The Islands (Classic, 8 Days, Boston Airport And Post Trip Hotel Transfer)

In-depth Cultural Family Sightseeing Historical +2

Colors of New England (Boston, MA to Portland, ME) (2024)

Spotlight on Boston

"I had such a blast. My tour guide was amazing and the group I was with were incredible." Alexis, traveled in August 2023

In-depth Cultural Coach / Bus Sightseeing Historical +2

Colours of New England

"Interesting variety of stops from rugged Maine to quaint Vermont to historic Boston with much in between." Carla, traveled in October 2023

Colors of New England

• €150 deposit on some dates

New England's Fall Foliage (Small Groups, 8 Days, Boston Airport And Post Trip Hotel Transfer)

Boston Cape Cod and The Islands (Small Groups, 8 Days, Boston Airport And Post Trip Hotel Transfer)

New England and the Hudson Valley

"It was a very good trip and as I remembered having done several in the past." Marlene, traveled in October 2022

New England's Fall Foliage (Classic, 8 Days)

"We saw so many historical sites and had a lot of fun along the way!" Darlene, traveled in September 2023

New England's Fall Foliage (Small Groups, 8 Days)

Boston Cape Cod and The Islands (Classic, 8 Days)

"Canolis, Cape Code Chips and Cape Codders on the bus was a nice touch! Thoroughly enjoyed the snacks on the bus." Paula, traveled in September 2021

Boston Cape Cod and The Islands (Small Groups, 8 Days)

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35+ Amazing Day Trips From Boston Massachusetts

Wondering where to go on a day trip from Boston? Boston has always been my most frequent city of travel. I’ve lived there too. Based on my own experience exploring the region, here’s my list of 35 great day trips from Boston.

Boston is perfectly situated in the northeastern region of the United States . This area of New England boasts gorgeous beaches, charming Colonial towns, seaside ports, and destinations steeped in history.

These destinations are all less than 2 hours away from Boston. Any more than 2 hours is just too far afield for a proper day trip.

Because of its central location, Boston makes a great launchpad for day tripping in New England. Boston is well-connected to other towns and cities. Boston’s main arteries (I-90, I-93 and I-95) give you easy access to Maine, New Hampshire, Connecticut, Rhode Island, Western Massachusetts, and even Vermont.

Boston’s main arteries (I-90, I-93 and I-95) give you easy access to Maine, New Hampshire, Connecticut, Rhode Island, Western Massachusetts, and even Vermont.

On a day trip from Boston, you can escape the city’s adoring (and sometimes maddeningly intense) crowds.

Best Day Trips From Boston

Here are my picks for the best day trips from Boston. I’ve given you a whopping 36 options, along with expected drive times. I’ve listed them in alphabetical order for ease of reference.

The options for Boston day trips are endless and incredibly varied. There’s something of interest for everyone, from culture vultures to history buffs to nature lovers.

You can pick what suits you most, whether you want to relax on the beach or explore a cozy New England town.

If pressed to choose, I’d have to say my top three picks for Boston day trips are Portland Maine (cool foodie city), Stockbridge Massachusetts (quintessential New England town), and Portsmouth New Hampshire (adorable arty village).

1. Bristol Rhode Island (1:10 Drive)

Bristol is a beautiful New England town that’s full of history and charm. With a red-white-and-blue painted stripe down Hope Street, it exudes Americana. 

Bristol has everything you need for a relaxing break from Boston — fine dining, bike trails, art galleries, and ocean views. A highlight of Bristol is its well preserved historic architecture. In Bristol, you’ll find Colonial, Federal, and Gilded Age buildings. 

Linden Place Museum features a stunning spiral staircase and movie memorabilia. Blithewold Mansion has immaculately curated gardens, hosts concerts in the summer, and offers dramatic harbor views.

If you like to hike or bike, the East Bay Bike Path will suit. It’s a 14.5 mile paved path connecting Providence and Bristol, which gives you panoramic views of Narragansett Bay.

2. Cambridge Massachusetts (5 minute drive)

The easiest day trip from Boston is to its next door neighbor, Cambridge. Historic Cambridge is a lively university enclave, with the Charles River as its playground and backyard.

Cambridge is home to the renowned Harvard University (where you’ll be wrapped in red brick) and the Massachusetts Institute of Technology (where you can admire eclectic modern architecture). You can book a walking tour of Harvard here and a tour of MIT here .

And it’s not just the universities that dazzle. In Cambridge, visitors can enjoy outstanding museums, a vibrant performing arts scene, and delicious haute cuisine restaurants.

The  Harvard Art Museums  are the best art spot, with a range of works from antiquity to present, including a prized Van Gogh .

Be sure to hang out in Harvard Square, the iconic center of Cambridge. It’s a triangular plaza located at the intersection of Battle Street, John F. Kennedy Street, and Massachusetts Avenue.

You’ll find all manner of humanity — students, tourists, political activists, buskers, chess players, and other street creatures.

You can also visit  Longfellow House . It’s located on Brattle Street, the historic road connecting old Cambridge and Watertown.

The house museum is famous as the one time home of Henry Wadsworth Longfellow. He was a novelist and poet who wrote stirring tales that thrilled 19th century America, including the  Midnight Ride of Paul Revere .

3. Cape Elizabeth Maine (2 Hour Drive)

Cape Elizabeth is gorgeous little town just south of the city of Portland. The town faces out into Casco Bay.

People have lived in Cape Elizabeth for thousands of years. In 1765, Cape Elizabeth officially became a town. For a glimpse of those early days, stop by the  Spurwink Meeting House . The austere white clapboard church was built in 1802.

The town’s stretch of coastline is stunning, dotted with lighthouses. The cliff walk is a lovely must do experience in Maine.

The 19th century Fort Williams Park in Cape Elizabeth guards the entrance to Portland. It’s home to the Portland Head Light. You can walk the park’s Arboretum trails, enjoy a picnic, or explore the fort’s old batteries.

3. Charlestown Massachusetts (5 minute drive)

Charlestown is Boston’s oldest neighborhood. It’s just across the river from the North End.

If you’ve walked the Freedom Trail in Boston, you’ve already been to Charlestown. The town is home to the Bunker Hill Monument and the USS Constitution, which are must visit landmarks in Boston .

In 1775, Charlestown was the site of one of the most important battles of the Revolutionary War. American patriots defeated the British in the Battle of Bunker Hill. Nearly the entire town was destroyed during the battle and it wasn’t rebuilt until after the war ended.

Nowadays, Charlestown is a pretty place that’s well worth a stroll. A sense of Colonial charm permeates the streets and parks of Charlestown. The town has a classic main street, town square, and pretty clapboard homes.

4. Chatham Massachusetts

A visit to Cape Cod is a no-brainer day trip from Boston. But where to stake your claim?

Try the inimitable charms of Chatham, a tony New England town. In Chatham, the homes induce jaw drops, the historic center is walkable, and the seafood is hauled in just offshore.

Chatham’s curving Main Street conjures up low key elegance and old world charm. Chatham is the only Cape Code town bounded on three sides by water. It’s consistently ranked as one of the US’ best beach towns.

Chatham Lighthouse Beach is considered the most scenic public beach. It’s set beneath Chatham’s iconic lighthouse. This wild stretch of the Atlantic is the place for long walks and sunbathing (the surf is rough).

If you need a dose of culture with your beach retreat, head to the Orpheum. It’s a restored vintage theater showing first run movies and classics.

Or, take in a play or musical at the Monomoy Theater, after browsing the casual to high end shops.

5. Concord Massachusetts (35 Minute Drive)

Just 15 miles north of Boston is the small town of Concord. It’s the perfect Boston day trip for literary buffs. Concord is a steeple-studded town home to pretty  Walden Pond . Walden Pond is a nature preserve that’s home to countless local flora and fauna.

Walden Pond is forever linked to novelist Henry David Thoreau. From 1845 to 1847, he lived in a one room cabin , the property of his friend and mentor Ralph Waldo Emerson. A replica of the original cabin is about half a mile from Concord.

There, he wrote one of America’s most famous novels,  Walden  or  Life in the Woods.   Walden  explored simplistic living, solitude, and harmony with nature.

In Concord, you can also visit Emerson’s House and Louisa May Alcott’s Orchard House . The novelist based  Little Women  on her experiences growing up in this house with her sisters.

Today, the historic home is a museum. It has 80% of its original period furniture.

You can tour the kitchen, dining room, parlor, art studio, and the bedrooms. Louisa’s bedroom has the small white desk where she penned  Little Women  and other books.

If you want to learn about Concord’s Revolutionary War and literary legacy, visit the Concord Museum . On display, you’ll find Native American artifacts, Thoreau’s snowshoes and furniture, Ralph Waldo Emerson’s study, Paul Revere’s original signaling lantern, and period collections of decorative arts and furniture.

If you want to pay homage to Concord’s famous authors, visit Sleepy Hollow Cemetery. You’ll find the final resting places of Thoreau, Emerson, Alcott, and William Ellery Channing.

6. Concord New Hampshire (1:10 Drive)

Concord is the capital of New Hampshire. It’s a sleepy New England town that I used to spend parts of the summer in. Founded in 1734, Concord embodies the American spirit. There are a fair number of things to do in Concord.

You can visit the New Hampshire State House, built in 1819. It sports a gleaming eagle topped gold dome, reminiscent of Boston’s own state house. The New Hampshire legislature still uses the original chambers.

Just steps from the capitol is the New Hampshire Historical Society. It boasts a sculpture by the famous Daniel Chester French.

You can also visit Pierce Manse, the former home of President Franklin Pierce. Via a guided tour, you can see period artifacts. Franklin’s grave is also in town.

7. Essex Connecticut (2 Hour Drive)

Essex just exudes small town charm. It has a bucolic setting on the banks of the Connecticut River. The town is consistently rated as one of America’s best small towns.

Essex seems halted in time, looking much as it did during the height of its ship building prosperity. Essex has a picture perfect harbor. It’s scattered with charming inns and historic architecture.

On Main Street, whitewashed houses jostle side by side, in early Colonial and Federal styles. Pop into the Griswold Inn, especially for its vaunted Sunday breakfast. The cute shop Good and Curiosities sells gifts with a historical theme.

Essex is famed for its riverboat tour, the Essex Steam Train & Riverboat. On a 2.5 hour tour, you can travel by train and boat through the countryside. By boat, you’ll glide by farms, inlets, coves.

8. Exeter New Hampshire (1 Hour Drive)

Exeter was founded in 1638 by Reverend John Wheelwright. This pretty new England town brims with charm at every turn. The beauty of Exeter will appeal to everyone from art lovers to history buffs to recreational seekers.

You can take a leisurely stroll in the quaint and historic downtown. You’ll find elegant buildings with shops, restaurants, art galleries, and more.

Or, walk down tree-lined streets to discover historic homes, including the Ladd-Gilman House that’s now the  American Independence Museum .

If you want to experience the great outdoors, Essex has hiking, biking, and water sports. During New England’s fall foliage season , the colors are truly breathtaking.

9. Hanover New Hampshire (2 Hour Drive)

As a graduate of Dartmouth College, Hanover is a sentimental favorite of mine. And it clocks in at 2 hours, my limit for day trips from Boston.

Forbes named Hanover one of America’s Prettiest Towns. For a remote rural town, Hanover packs a surprising cultural punch.

The best place to get your art fix is the wonderful Hood Museum of Art . It’s one of the oldest teaching museums in the country. It has a large collection of artifacts and art dating back to Assyrian culture in 900 BC.

But it’s not all ancient. The museum has a surprisingly good collection of contemporary art, with works by Rothko and Ed Ruscha. It also showcases contemporary African and Native American art.

You should also pop into Baker Library. You’ll find eye catching murals by Jose Clemente Orozco in the reading room.

Hanover is also home to the Hopkins Center for Performing Arts (the “HOP”). There, you’ll find a wide variety of performing arts — plays, shows, concerts, special events, movies, etc.

Here’s my itinerary for spending  one day in Hanover . In addition to just driving to Hanover, you can take the Dartmouth Coach from Logan Airport.

10. Hartford Connecticut (1:35 Drive)

Hartford is one of the oldest cities in the United States. It makes a great day trip from Boston if you want to visit another city. The capital of Connecticut is home to historic sites, art museums, and beautiful parks.

It’s also the birthplace of Mark Twain, a culinary powerhouse, and home to one of the best “little downtowns” in New England.

The Mark Twain House & Museum is a national historic landmark. The museum has it all: inspiring architecture, gorgeous interior design, lovely grounds, and fascinating stories about its owners. It offers visitors an opportunity to learn about the novelist Mark Twain, his family, and his legacy.

Another good reason to visit Hartford on a day trip from Boston is to visit the magnificent Wadsworth Atheneum Museum of Art . The castle-like museum is one of the best museums in New England .

The Wadsworth first opened its doors in 1844. It’s since grown to a collection of over 50,000 works of art from over 5,000 years. There are significant works of modern and contemporary art.

You’ll find works by Frans Hals,  Caravaggio , Orazio Gentileschi, and Bernardo Strozzi. There’s a beautiful painting by pre-Raphaelite artist William Holman Hunt called  The Lady of Shallot . There’s also an American art collection, with works by John Singleton Copley and Charles Wilson Peal.

11. Keene New Hampshire

Keene is a beautiful hidden gem in New England’s Monadnock Region. A lively college town, Keene combines culture and the great outdoors.

Keene offers stunning brick streets, charming maple farms, and quaint specialty shops. Keene even has a white clapboard church with a soaring steeple, the United Church of Christ.

Keene is also home to one of the loveliest and widest main streets in New Hampshire. The historic downtown area is centered on Central Square. It’s an eclectic mix of old time shops, bookstores, and funky craft stores.

Keene is also home to covered bridges and museums. The Horatio Colony House and Nature Preserve is housed in a 1806 Federal style building. The museum houses historical artifacts for the history buff. The nature preserve offers miles of hiking trails for the nature lover.

12. Kennebunkport Maine (1.5 Hour Drive)

Kennebunkport is a classic beauty, one of the most beautiful towns in New England . It’s effectively the Hamptons of the Pine Tree State, known for its dramatic mansions. To see them, take a drive between Kennebunkport and its sister town Kennebunk.

Kennebunkport has a lively downtown, the epicenter of which is called Dock Square. It’s chock full of restaurants, boutiques, and art galleries.

There are plenty of patio cafes for people watching perches. The Clam Shack serves up fried claims and lobster rolls.

For a walking tour of Kennebunkport’s historic buildings, start at the Brick Store Museum on Main Street. Head south and you’ll see several extraordinary structures from the 18th and 19th centuries, including Lexington Elms, Horace Porter House, and Benjamin Brown House.

Summer Street is also an architectural showcase, with an array of Federal and Colonial buildings. To get the complete scoop, you can take a guided 90 minute tour of Kennebunkport’s National Historic District. Buy tickets at the Brick Store Museum.

If you want to hit the beach, try Gooch’s Beach along the Victorian-lined Beach Avenue. Or drive 10 minutes north to the beautiful 3 mile long Goose Rocks Beach.

If you’d like to take a day tour from Boston, this excellent tour combines history and lobster. If you’d just like a guided walking tour once you’ve arrived in Kennebunkport, click here for a 2 hour historic tour.

13. Kittery Maine (1 Hour Drive)

The small town of Kittery is just a short drive from Boston. It’s located on the border between Maine and New Hampshire and is linked by bridges across the Piscataqua River.

Kittery was once known for its shipbuilding. Nowadays, people day trip to Kittery from Boston mostly for its shopping. Kittery has both outlet malls and boutique craft shops. You’ll find stores like Crate and Barrel, Le Creuset, Lululemon, Under Armour, and Nike.

If the weather is warm, head to the beach for a swim. Seapoint Beach is a picturesque shoreline perfect for a dip or a stroll.

You can also visit Fort McClary State Park . It’s a unique historic site that was formerly a defensive military fortification. It has stood for over 275 years protecting the mouth of the Piscataqua River at the entrance to Kittery.

14. Lenox Massachusetts (2 Hour Drive)

Lenox is the perfect day trip from Boston for art lovers. It’s a pretty town of art galleries and upscale boutiques housed in historic buildings.

You’ll find iconic properties like Blantyre, Wheatleigh, Canyon Ranch, and The Mount. At one point, there were so many lavish summer homes that Lenox was known as “the inland Newport.”

In 1902, Edith Wharton, the first woman to win the Pulitzer Prize in Literature, built  The Mount . It was a stately country retreat for the literary lioness and her then-husband. The Mount was modeled after European mansions, but lacked without their ostentatious excesses.

The Mount is home to a summer lecture series, weekly bird walks, concerts, theater performances, and outdoor sculpture exhibits. Edith Wharton’s library has been returned to the house, with 22 first editions of her work.

Lenox is also home to  Tanglewood , the summer home of the Boston Symphony Orchestra. Tanglewood is a must do for music lovers. You can hear symphony orchestras, solo performances, and world class musicians.

15. Lexington (30 Minute Drive)

If you’re a student of U.S. History, Lexington should ring a bell. In 1775, the American Revolutionary War started in Lexington and nearby Concord. Lexungtin is the best day trip from Boston to immerse yourself in Revolutionary war history.

Lexington has more than 10 historic battle sites, cemeteries, and memorials that you can tour. You can see the site of the first battle of the Revolutionary War.

A renowned statue by sculptor Henry Hudson Kitson marks  Battle Green , where the Colonial Minutemen clashed with British troops. In Minuteman National Historical Park, you can see a multimedia exhibit on the Road to Revolution .

While waiting for the British, the Minutemen and their commander, Captain Parker, gathered in the  Buckman Tavern . The interior is preserved exactly as it appeared in the 18th century, complete with the original seven foot wide open fireplace. The old front door still contains British musket-ball holes.

Wrap up your tour of Lexington by seeing the Lexington Depot historic train.

16. Madison Connecticut (2 Hour Drive)

Madison is a shoreline town only East Coasters know about. This beautiful New England day trip from Boston proves the adage that good things come in small packages.

With a population of only 18,000+ residents, Madison delivers a major dose of quintessential New England charm. During his time at Yale, Bill Clinton was so taken with Madison that he mentioned it in his memoir,  My Life , calling it “especially old and beautiful.”

One of the main draws of Madison is Hammonasset Beach State Park . There you’ll find two miles of beaches, wetlands, woodlands, and a nice boardwalk.

The town itself is charming and pedestrianized, full of shops and cafes. A popular haunt is RJ Julis Booksellers, one of the nation’s finest independent shops for book nerds looking for the perfect read.

Madison is also a culture-filled hamlet. A fun outdoor activity is walking the Sculpture Mile . Created by the Hollycroft Foundation, it offers a unique museum-like exhibition that features art work by some of the nation’s most significant sculptors.

17. Manchester New Hampshire (1 Hour Drive)

You might think New Hampshire is all mountains and lakes. But it also boasts a rich cultural history. In particular, Manchester has some fine art offerings that merit a day trip from Boston.

Manchester is home to the state’s only fine art college, the New Hampshire Institute of Art. It also has an internationally acclaimed museum, the  Currier Museum   of Art .

The museum’s permanent collection includes works by Picasso, Monet, Rothko, Wyeth, and O’Keefe. It hosts touring exhibitions. The museum also manages Zimmerman House, designed by architected  Frank Lloyd Wright . It’s the only Wright house open to the public in New England.

Manchester also has a premiere contemporary arts gallery, the Gallery of the New Hampshire Art Institute. It’s multi-functional, serving as an art center, lecture hall, and performance theater. On display you’ll find a diverse mix of traditional and modern art forms, from photography to installation art.

18. Mystic Connecticut (2 Hour Drive)

Mystic is calm and exquisite, a charming waterfront town set on the shores of the Mystic River. It’s quaint downtown is filled with boutiques, galleries, and eateries.

On Main Street, you’ll find Mystic Pizza , made famous by a kitschy 1980s movie. Mystic’s main landmark is Bascule Bridge, the most photographed bridge in Connecticut and a perfect spot for river views.

Mystic Seaport is Connecticut’s #1 attraction, an example of “living history.” It covers 19 acres along the Mystic River.

There are indoor and outdoor exhibits, including four vessels that are National Historic Landmarks. You can climb aboard or peruse the recreated village.

19. Newburyport Massachusetts (1 Hour Drive)

First settled in 1635, Newburyport is an immaculate seaside town. It has a classic New England feel — with red brick streets, lobster shacks, and cobbled lanes. Plus, “the Port” is only 35 miles from Boston, making it the perfect day trip or weekend getaway.

State Street is the heart of Newburyport. You’ll find an eclectic treasure trove of shops — clothing boutiques, bookstores, cafes, and vintage shops. The Firehouse Center for the Arts is Newburyport’s cultural hotspot, offering concerts, musicals, and plays.

When you tire of shopping, surf and sand lovers can hit the beach. Plum Island is only a 20 minute drive from Newburyport.

Plum Island has beautiful and beloved sandy beaches and dunes. And it’s home to the Parker River National Wildlife Refuge, a hidden gem sanctuary with prime bird watching opportunities.

20. Newport Rhode Island (1.5 Hour Drive)

Just two hours south of Boston lies the tony coastal town of Newport. Founded in 1639, Newport is a treasure trove of historic European-style mansions set against ocean views.

Think the Gilded Age’s Astors, Vanderbilts, and Kennedys — families who built the first palatial mansions in the US. Newport is a fancy place.

Most of the mansions are on Bellevue Avenue and a few are on the waterfront. Built by Cornelius Vanderbilt, Breakers Mansion is Rhode Island’s #1 attraction. It’s located on the scenic 3.5 mile Newport Cliff Walk .

If you’d like to tour the magnificent mansions of Newport, this is an excellent day tour from Boston .

The Newport Art Museum is the core of the creative community. The Artists’ Open Space serves up local and regional shows year round.

There’s a dozen commercial galleries in town as well. Island Art is the best, noted for its contemporary pieces.

On the performance arts side, Newport really excels. It offers up everything from Shakespeare plays in Queen Ann Square to musical festivals dedicated to jazz, classical, and folk music in July and August. There’s also the Newport Fine Arts Festival in September.

21. Old Sturbridge Village Massachusetts (1 Hour Drive)

Old Sturbridge Village is a living history museum located in Sturbridge Massachusetts. The museum recreates life in rural New England as it was during the 1790s through 1830s. 

There’s a working farm with heritage breed animals, historic buildings, and horse drawn sleighs. Costumed historians are very engaging and will regale you with historic tales.

You can walk the village and meet the skilled craftsmen who still practice their trade. You can also take a wagon ride. The Village offers several events throughout the year — Winter Photo Walk, Sunday Brunch, and Dinner in a Country Village.

22. Ogunquit Maine (1:30 Hour Drive)

Feeling like a beach day? Nestled along the coast, tiny Ogunquit has been a resort village since the 19th century.

The word Ogunquit translates to “beautiful place by the sea.” You can see why immediately. Ogunquit is like a mini Provincetown. 

The town is a popular summer beach destination in New England, and I came here often as a child. Ogunquit has two beautiful long beaches, Ogunquit Beach and Footbridge Beach. Footbridge is the quieter of the two beaches.

Ogunquit is most renowned for its coastal path, the Marginal Way . It’s a paved 3 mile seaside stroll, starting at Ogunquit Beach and meandering to Perkins Cove.

Perkins Cove is a tiny artisans village, filled with sea-weathered buildings, where you’ll find some art galleries and seafood eateries.

23. Northampton (2 Hour Drive)

Just under 2 hours from Boston, the rural town of Northampton is a cultural nerve center in New England. It’s a pretty town, ringed by 5 colleges and college museums.

Grand mansions line tree-shaded streets. The beautiful Main Street is filled with with shops, art galleries, bookshops, etc.

In downtown Northampton, there are more than a dozen visual arts venues. The Northampton Center for the Arts offers poetry readings, film screenings, and concerts. The Calvin Theater is the premiere concert venue, hosing major touring music and comedy acts.

Four of the five colleges near Northampton offer theater and visual arts. Smack in the middle of Northampton is Smith College. Its beautiful  Smith College Museum of Art  just received a $35 million makeover. The museum offers a year round series of art lectures, contemporary art exhibitions, and films.

Just down the road is  Mount Holyoke College Art Museum . It offers contemporary and traditional exhibitions year round.

You can also admire contemporary work at Amherst’s Mead Art Museum or check out national and international exhibits at Amherst’s University Gallery.

Northampton has a good foodie scene too, with both great pizzerias and haute cuisine. There are two dairies nearby, so the town’s cheese and ice cream options are among the best in New England.

24. Peterborough New Hampshire (1:30 Hour Drive)

Peterborough is a charming New Hampshire hamlet set along the Contoocook River. Peterborough is rich in art and culture, with a charming downtown centered on Depot Square. Thornton Wilder’s Pulitzer Prize winning play,  Our Town , was based on Peterborough.

Peterborough has two theater groups and a renowned artist colony, The MacDowell Colony. The colony is the oldest artist’s retreat in the US, hosting many exhibitions. 

In 1997, it was awarded the National Medal of Arts. Peterborough is also known for its antique shops and galleries.

Nature lovers can head to Miller State Park , which has several trails (and a road) leading to the summit of Mount Monadnock. Edward MacDowell Lake has trails as well, in addition to a beach and boat ramp.

25. Plymouth (45 minutes)

Situated at the mouth of Cape Cod Bay, Plymouth is a historical haven for Boston day trippers. The town was the very first permanent settlement by Europeans north of Virginia. Today, it’s a thriving small town with a lovely historic district, perfect for history buffs.

After parking, first head to the  Mayflower II . It’s is a full scale replica of the original 17th century Mayflower.

The Mayflower is famous as the ship that brought pilgrims to the US in 1620. You can even take a tour of the ship itself, which is docked in Plymouth Harbor

Also, to learn the pilgrims’ tale, stop in the state’s oldest museum,  Pilgrim Hall . There, you’ll find an unmatched collection of ancient artifacts and possessions of the pilgrims. Afterwards, you’ll get to wander around historic  Howland House  and visit the 18th century Court House.

If you want to really step back in time, head to  Plimoth Plantation . It’s a living museum that aims to explore the daily lives of the Colonial Americans. The village has been carefully recreated, with thatched roofs and giant open fireplaces.

The actors in the museum are in period costume and never step out of character. You can watch them performing 17th century tasks including building, gardening, and military exercises.

26. Portland Maine (1:45 Hour Drive)

 Located on a peninsula jutting into Casco Bay, Portland is a rare metropolis in a state filled with small hamlets. It’s a hip and laid back place that almost seems too cool for one of  New England’s most beautiful towns . Portland is a great day trip from Boston for foodies.

Portland has myriad cultural offerings and is a bastion of historical preservation. The restored Old Port is a warren of cobbled streets with a movie set feel. This area is filled with vibrant Victorian buildings and buzzing farm to table eateries.

Start on Commericial Street, the main drag, and work your way inward. The Old Port is known for its cobblestone streets, 19th century brick buildings, and fishing piers. It’s also a hive of activity.

In downtown Portland, there’s a thriving art school, infusing the city streets with creative types. And there are 24 commercial art galleries.

Opened in 1983, Portland’s crown jewel and premiere art destination is the  Portland Museum of Art , an architectural masterpiece designed by I.M. Pei of  Louvre  fame. Its innovative architecture allowed curators to redefine the art viewing experience.

Restaurants and coffee bars are filled with visual art. In June, the revived downtown hosts the Old Port Festival, described as “part freak show, part art festival, part fashion parade.”

Portland is also a hot spot for restaurants, coffee shops, and entertainment. Did I mention breweries? Beer lovers will be happy to know that Portland has 18 breweries all its own. It’s the Craft Bew Capital of America.

If you want to delve more deeply into Portland’s foodie culture, there are some awesome tours.

This tour takes you on a culinary walking tour of the Old Port and this tour lets you feast on seafood in the Old Port. If you’re a fan of craft beer, this tour gives you a taste of Portland’s amazing brew pubs.

27. Portsmouth New Hampshire (1 Hour + Drive)

The New Hampshire town of Portsmouth has also made an appearance on Forbe’s list of America’s Prettiest Towns. Portsmouth is a small town in southern New Hampshire along the Piscataqua River. 

Portsmouth is a great Boston day trip destination for art lovers and foodies. It’s known for its upscale farm to table eateries and art galleries.

Portsmouth’s funky downtown is adorable, with activity centered on Market Square. You’ll find classic white steepled churches, rustic brick shops, and sidewalk cafes. Portsmouth Book & Bar combines books, coffee, and live events.

History lovers should check out the Strawbery Banke Museum . It’s a 10 acre outdoor museum featuring period gardens, preserved historic buildings and detailing the story of how the Portsmouth settlement was founded. 

There are 39 historic buildings dating from 1695 to 1820. The Goodwin Mansion is the most impressive.

Prescott Park is a waterfront park near Strawberry Banke, which is great place to picnic. Enjoy the gardens and the Prescott Park Arts Festival, featuring concerts and foodie events.

in 2017, Travel & Leisure called Portsmouth the “Christmas Capital of North America.” It’s a wonderful New England Christmas destination. “Vintage Christmas” is a month long celebration kicking off December 1. A trolley does a loop of the downtown and a candlelight stroll is held on weekends.

Here’s my guide to the best things to do in Portsmouth in one day .

28. Providence Rhode Island (1 Hour Drive)

Nicknamed the “cooler city” by GQ, Providence is one of the  best towns on the East Coast . Providence is home to an Ivy League college, design schools, and a culinary institute. 

The city is a hodgepodge. It combines big city sophistication with small town charm. It has a vibrant local culture, celebrated restaurants, and sparkling waterfront parks. Providence is full of historic Yankee monuments, but also has a young and funky vibe.

Providence is an easy day trip from  Boston , less than an hour away. But this little jewel box of a city is often overlooked by travelers and definitely underrated. So much the better for its admiring visitors.

Be sure to explore Providence’s Little Italy on Federal Hill. Then, head to the East Side to encounter Providence’s Colonial past. Benefit Street is a bucolic 1.2 mile walk that’s an architectural showcase.

You’ll see some of the most beautiful Federal era architecture in the United States. You’ll also find the lovely campus of Brown University.

And you can’t leave Providence without visiting the fabulous  Rhode Island School of Design Museum . A major cultural institution in the United States, RISD houses over 100,000 works. It’s one of the best small museums in the world .

READ: 1 Day Itinerary For Providence

29. Provincetown Massachusetts (2 Hour Drive Or Ferry)

Do you want to combine a day at the beach with great art? head to Provincetown. The pretty town is tucked away on the far end of Cape Cod.

It’s been attracting artists and creative types for more than a century. Eugene O’Neill wrote his first play here. Modern art luminaries like Helen Frankenthaler, Marsden Hartley, and Hans Hofmann had studios here.

Nowadays, there are 60 art galleries scattered down Provincetown’s picturesque streets. It’s the perfect place for art lovers on the East Coast.

The town’s premiere art venue is the Provincetown Art Association and Museum on Commercial Street. The museum highlights local and New England artists with single artist and themed shows.

The Schoolhouse Center for Art & Design is home to several galleries as well. The Silas-Kenyon Gallery focuses on contemporary art. If you like vintage photography, head to the Driskel Gallery.

The big ticket art festivals you should have on your radar are the Spring Arts Showcase Weekend in May and the Fall Arts Festival in September and October. There’s also an International Film Festival in June.

Don’t forget to eat some lobster, preferably at the Lobster Pot . You can go wine tasting at  Truro Vineyards  or sip craft beers at the  Provincetown Brewing Company .

If you visit Provincetown in the summer, you could spend hours in traffic at the Sagamore Bridge if you drive. But you can also take the Providence Ferry . The fast ferry runs direct from Boston to Provincetown from mid-May through mid-October. It’s only 95 minutes each way.

30. Rockport Massachusetts (55 Minute Drive)

I f a stunning seaside town is on your Boston day trip agenda, head to Rockport. This little town is on Cape Ann, the “other” cape in northeast Massachusetts. There’s a reason why North Shore residents treasure Rockport as a lovely weekend getaway.

There are plenty of things to do in Rockport. Stroll around and admire all the fishing boats and painted cottages. Check out the shops and art galleries on Bearskin Neck, a cute area perched on the edge of town.

Sample some fudge at Rockport Fudgery , eat lobster rolls, relax on the beaches, or take a walk along the rocky coastline at  Halibut Point State Park . You can even go on a  Cape Ann whale watch .

31. Rye New Hampshire (1:10 Hour Drive)

Another good beach option is Rye. The picturesque town of Rye is home to the best beach on the 18 mile long New Hampshire shoreline.

First settled in 1623 on Odiorne Point, Rye is the birthplace of New Hampshire. Rye is largely undeveloped because it’s subject to strict zoning laws.

Rye is a serene contrast to the more frenzied Hampton Beach down the road. In Rye, the tide is small and rolling. It’s a perfect place for a beginner surfer.

You can also take a scenic drive down Route 1A past Millionaire’s Row and ogle at Rye’s breathing early 20th century mansions.

32. Salem Massachusetts (45 Minute Drive)

Even if you haven’t traveled in Massachusetts , you’ve probably heard of Salem. Known as the “Witch City,” Salem is a beautiful seaside town and an easy day trip from Boston.

In Salem, you can learn about Salem’s creepy past as the “witch capital” of the United States. Salem embraces its notorious past, when the infamous 17th century Witch Trials defined the town.

Salem is replete with whimsical magic shops, all things haunted horror, and ghostly tour options. Many of Salem’s top attractions are devoted to its witchy history. This means that the best time to visit Salem in during Halloween.

Salem is also famous for its beautiful 17th century Colonial and Georgian architecture and delicious seafood. Essex Street is the historic cobblestoned district, with the original brick  Old Town Hall .

Old Town Hall dates from 1816. The second floor still stands as a public hall and the first floor is used as a public art space.

If you’re a literary fan, you should visit the  House of the Seven Gables . Built in 1668, it’s one of the oldest Colonial mansions still standing in the United States. Nathaniel Hawthorne immortalized the house in his 1851 novel of the same name.

Inside, you’ll find a recreation of the secret staircase from the novel. The house where Nathaniel Hawthorne was born is also on the property.

Click here to buy ferry tickets to Salem.

There are some excellent guided tours in Salem. If you’re a history buff and want to take a witchcraft trials walking tour, this is an excellent guide . If you’re staying overnight in Salem, you can also take this haunted history nighttime tour or this ghosts of Salem walking tour .

33. Stellwagen Bank National Marine Park (30 Minute Drive)

Want to view some of the most massive animals on the planet? The  Stellwagen Bank National Marine Park  is one of the best whale watching spots in the entire world. It’s a wild ocean destination not far from Boston, just 37 miles away.

The sancturay has an extremely productive and diverse environment, which encourages a wide mix of marine wildlife.

Each summer, around 50 recognized humpbacks return. You can also spot dolphins and seals. There are plenty of whale spotting tours available in the area departing from Gloucester or Provincetown. Click  here  for a list of boat tour operators.

34. Stockbridge Massachusetts (2 Hour Drive)

Stockbridge is the quintessential New England town. It’s one of my favorite day trips from Boston.

Stockbridge was settled in 1734 by British missionaries. It’s blessed with simple charm and a fabulous line up of cultural attractions.

Three of the greatest American artists and authors called Stockbridge their home — Edna St. Vincent Millay, Herman Melville, and Norman Rockwell. One of America’s greatest treasures is the  Norman Rockwell Museum .

Rockwell was one of the greatest artists and illustrators in American history. Stockbridge was Rockwell’s long time residence and what he called his “best studio yet.”

You can also visit  Chesterwood , the home of Daniel Chester. It’s a 1920s Colonial Revival house.

It comes complete with the soaring studio of the legendary sculptor and landscape architect. Chester created the statue of President Lincoln seated in the Lincoln Memorial in Washington D.C., and you’ll see plaster models in the museum.

Every summer, Stockbridge (along with Lenox) hosts the Tanglewood Music Festival. It’s a series of concerts across all musical disciplines.

Stockbridge is also home to one of the Berkshires Gilded Age “cottages,”  Naumkeag . You can tour this quirky 44 room mansion designed by Stanford White, a famed starchitect of the time.

 35. White Mountains, New Hampshire (2 Hour Drive)

It’s a hike to get to the White Mountains from Boston. But it’s worth the long drive to spend a day immersed in nature.

The White Mountains are New Hampshire’s premiere attraction. It’s the best day trip from Boston for fall foliage .

The White Mountains are incredibly beautiful, with plenty of natural wonders. They’ve long attracted vacationers, photographers, and adventurous hikers and skiiers. Mount Washington is the Northeast USA’s peak of superlatives. 

The sinuous Kancamagus Highway in the White Mountains is the granddaddy of New England drives. It’s a scenic 35 mile stretch of highway. You’ll be dazzled by the incredibly unspoiled scenic views along the way.

There a few pullouts for trailheads, providing great photo and hiking 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.

 In Crawford Notch State Park , 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.

Don’t leave without experiencing the  Mt Washington Cog Railway . It’s a historic train ride up to the summit of Mt. Washington. The mountain is the tallest one in the northeastern United States at 6,289 feet.

Aside from driving around soaking up the scenery, you can explore the cute downtown of North Conway, relax at  White Lake  in Tamworth, do a canopy tour at  Bretton Woods , go on a  waterfall hunt  near Conway. 

36. Worcester (1 Hour Drive)

Right in the heart of Massachusetts, Worcester is one of the best day trips from Boston. Worcester is the second largest city in Massachusetts after Boston. It’s just an hour away from Beantown.

Once in Worcester, take a gander through the huge exhibitions at the  Worcester Art Museum . You can easily spend a good few hours inside. The museum has works of Impressionism, Roman mosaics on the Renaissance Court floor, medieval armor, and Paul Revere’s silver collection.

Be sure to visit the  Bancroft Tower . On the National Register of Historical Places, it’s been around in Worcester since 1900. This fantasy medieval castle was built on a whim to honor a US Navy pioneer. It’s a miniaturized castle in the middle of a park.

At night, you can take in a theater or music performance at the elegant Hanover Inn, Mechanics Hall, or Tuckerman Hall.

I hop you’ve enjoyed my guide to the best day trips from Boston. You may enjoy these other New England travel guides:

• 3 day itinerary for Boston
• 1 day in Hanover New Hampshire
• 35 Landmarks in Boston
• 10 day itinerary for New Hampshire
• Berkshires Road Trip Destinations
• Hidden Gem Towns on the East Coast
• 10 day itinerary for coastal Maine
• 7-10 day itinerary for Vermont
• One week itinerary for southern New England
• Fall foliage road trip in New England

If you’d like to take some day trips from Boston, pin it for later.

4 thoughts on “35+ Amazing Day Trips From Boston Massachusetts”

Nice collection of day trips, but with the review of Salem, MA I can’t believe you left off both the Peabody Essex Museum (one of the best art and culture museums in New England) and no mention of any of the NPS sites and all the maritime history this city has.

I know the Peabody Essex Museum is amazing. I’ve written about it in my Salem article and in my article on the best museums in New England. I will add something here. But with a round up post, you can only write so much for each town.

This was definitely a trip down memory lane. I lived in New England for 23yrs and visited many of these destinations. You certainly did a great job on the history. I especially enjoyed the colorful pictures. I am drooling over just the thought of the lobster rolls on the Maine and New Hampshire coast.

I would love a lobster roll right now!

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Last Updated on July 4, 2023 by Leslie Livingston

Ultimate Boston Bucket List: 50 Best Things to Do in Boston (2024)

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Boston, Massachusetts is an essential New England destination. In fact, it’s the first stop on my epic New England road trip itinerary . You won’t be at all surprised to hear that there are tons of fun things to do in Boston.

As New England’s biggest and most famous city, Boston is where old meets new. The convergence of historical sites and modern attractions can be seen within every cobblestone street and modern shopping center. You can start your day at Paul Revere’s House and end your night on a downtown rooftop bar. The possibilities are endless.

If you’re planning to spend some time in Boston, there’s no shortage of amazing activities, experiences, and food to be had here. From the world-class museums and trolley rides to seaside restaurants and quirky ghost tours , Beantown checks all the boxes. To make sure you do and see all the best this city has to offer, here is my ultimate things to do in Boston bucket list: 50 fabulous things to do in the city!  

Table of Contents

Wander the Museum of Fine Arts.

This behemoth of an art museum, located on Huntington Ave, has over 100 galleries that display only a fraction of its massive 450,000-piece collection. Over 1 million visitors wander the MFA each year to view artifacts from the Americas, Folk and Contemporary, Egyptian mummies, famous impressionist painters, and special traveling exhibitions. Tickets sell out fast, so purchase them in advance to ensure you get in.

Read Next:  Go Boston Card vs Boston CityPASS: Which is Better?

Make friends with penguins at the New England Aquarium.

For the aquatically inclined, the New England Aquarium is not to be missed. This massive public aquarium, found right in Boston’s lively seaport neighborhood, is home to an incredible collection of over 600 aquatic species. Visit any day of the week to see its giant squid, turtles, or penguins during feeding (one of our favorites!). Challenge yourself – can you catch a glimpse of every single one of the 20,000 types of animals living here?

Admire the Isabella Stewart Gardner Museum. 

I think that the Isabella Stewart Gardner Museum is one of Boston’s hidden gems. Although, it’s becoming more well known as people learn about the art heist that took place there. In 1990, a legendary art heist unfolded (history’s biggest art heist, in fact) during which 13 famous works of art were stolen without a trace. Over 20 years later, there are still no real leads on the theft or missing art, although there are some fascinating podcasts and documentaries out there.

But the heist aside, this fine art museum is well worth the visit, and the building is a work of art itself. You could spend hours perusing the glorious collection that Mrs. Isabella Stewart Gardner amassed and loved. 

I adored my visit to this museum. It is stunning throughout, from the iconic courtyard to the gorgeous works of art. And what is especially fascinating is that the frames of the stolen pieces still hang, an eerie reminder of what was lost.

Shop and dine at Faneuil Hall Marketplace.

Dubbed by America’s Founding Fathers in 1742 as “The Cradle of Liberty,” Faneuil Hall Marketplace has cobblestone promenades, impressive sweeping architecture, and over 70 retailers of specialty carts, locally owned shops, and restaurants. As Boston’s most popular shopping and dining spot, you can stay entertained here for hours on end.

Catch a Red Sox game at Fenway Park.

Home to the MLB’s Boston Red Sox since 1912, Fenway Park is beloved by locals and visiting fans alike. See the Green Monster for yourself (both the green right field wall, and Wally the mascot!), cheer on Boston’s team, and indulge in overpriced snacks. What a wholesome all-American pastime!

Stroll the grounds of Boston Common. 

Boston Common , a 50-acre park at the center of the city, is often considered the heart and soul of Boston. It’s also the oldest public park in America, established in 1634 (before our nation’s founding!). Today, people love to jog, lounge, converse, and attend fun events here. In the winter, ice skating on Boston Common Frog Pond is a must-do activity.

Explore the first botanical garden in America.

Right next to Boston Common is the Boston Public Garden , the first botanical garden in America. With a gorgeous Victorian design, vibrant floral patterns, fountains, monuments and the Lagoon, the Public Garden is simply delightful. It’s a romantic spot, so don’t be shocked if you accidentally stumble upon a wedding!

Travel tip: Find the ‘Make Way for Ducklings’ sculpture near the corner of Charles and Beacon Street, it’s totally adorable. 

Have fun with your kids at the Boston Children’s Museum.

Bringing the whole family to Boston? Your kids will have an amazing time playing at the Boston Children’s Museum . Created for educating and bringing joy to children, this museum has various exhibits that teaches kids to be curious, investigate using their senses, build, and use their creativity. Plus, you don’t have to be young to enjoy bubbles!

Read Next:  19 Awesome Things to Do in Boston with Kids

Learn about our 35th president at the JFK Library & Museum.

Interested in the life of John F. Kennedy? Well, Boston has the JFK Library & Museum , a building entirely dedicated to his life and legacy. You can explore permanent exhibits about his childhood, inauguration, the space program, First Lady Jacqueline Kennedy, and much more.

Tour the Mount Auburn Cemetery.

Mount Auburn Cemetery in Cambridge is not your average burial ground. This expansive cemetery, where 100,000 people are buried, is also a National Historical Landmark, a botanical garden , and the resting place of many renowned individuals. From artists and poets like Winslow Homer and Henry Longfellow, to activists, inventors, and Supreme Court Justices, there are so many memorable lives to commemorate here. 

Jam out at Wally’s Cafe Jazz Club.

Curious about delving into the world of jazz, or just a lover of live music? Wally’s Cafe Jazz Club is the place to beat. This classy, old-school jazz club hosts local student performers 365 days a year. Get cozy in this historical building and unwind to some top-notch jazz and blues, performed by musicians mastering their craft.

Watch an art-house film at Brattle Theatre.

Brattle Theatre in Cambridge is a rare establishment. This repertory movie theater located in the charming Brattle Hall has only one screen, featuring just one movie at a time. It was established with the purpose of highlighting indie, art-house films, as well as foreign films and first-run films. You’ll find some cutting-edge cinema here, so stop by Brattle Theatre and watch something you can’t find in normal theaters.

Ride glow-in-the-dark swings at the Lawn on D.

Ever swung on a glow-in-the-dark swing? Well, a nighttime visit to the Lawn on D is your chance. This innovative outdoor event space has a big lawn and concessions, and it frequently hosts live concerts and other lawn game events. But most people know it for its O-shaped hanging swings that glow at night. They make for awesome photo ops (and just a generally fun time!). 

Learn about dinosaurs at the Museum of Science.

Located in Science Park, the Museum of Science is nothing short of a house of wonders. This part-science museum, part-indoor zoo has imagination-sparking educational exhibits, interactive installations, and life-sized dinosaur models! You’ll leave knowing significantly more about human anatomy, technology, and natural history, and have a great time in the process. 

My toddler son loved our recent visit to the Museum of Science Boston, and he especially enjoyed the massive planet of Mars suspended in the atrium area.

As for my husband and I, we couldn’t get enough of the robot dog from Boston Dynamics. Amazing stuff. The photo above shows one of the robotic dog models up close, but you could watch one in action behind the window to the right. Of course, after it does one pass around the space, you have to wait for it to lay down again and charge up a bit!

Witness American history at the Boston Tea Party Museum.

History buffs will get totally swept away in the legendary Boston Tea Party story at the Boston Tea Party Ships & Museum. This amazing floating history museum is the definition of living history. Climb abroad replicas of the very ships docked at harbor in the 1700s, watch live reenactments, and stop by the tearoom for a taste. The thrilling 250th anniversary of the Boston Tea Party was just celebrated in December 2023 and hundreds of people turned out to join the occasion.

Visit Bunker Hill Monument.

Bunker Hill Monument in Boston, a 221-foot granite obelisk reminiscent of the Washington Monument in Washington D.C., commemorates the Battle of Bunker Hill. This famous battle was one of the first significant engagements between Patriots and British soldiers in the Revolutionary War. There is a spiral staircase that will take you to the top of the monument as well, making for spectacular 360-degree aerial views. 

Find unique architecture at Trinity Church.

If you enjoy spotting unique church architecture when visiting a new city, Trinity Church is a beautiful one. This historical church was founded in the 1700s and was an important site during the American Revolution. Its original building actually burned down in 1776 but was subsequently rebuilt and now serves as an important pillar of the Boston community. 

Get your car fix at the Larz Anderson Auto Museum.

Do you love cars? Located in Brookline at the Anderson Carriage House is the oldest collection of motorcars in the United States. Larz Anderson Auto Museum houses a fantastic array of historical motorcars from the 1800s through the 20th century. And even the manicured museum grounds themselves are worth seeing!

Walk in Paul Revere’s footsteps at Old North Church.

Ever hear of Paul Revere’s famous ‘Midnight Ride’ through Boston? In 1775, Old North Church was his first stop on the ride, where he instructed two Patriots to climb to the steeple and hang lanterns to warn of British troops approaching. Aside from this fascinating piece of history, Old North is also the oldest church in the city and a National Historic Landmark. 

Visit the oldest commissioned ship in the United States Navy.

The USS Constitution is in the Charlestown Naval Yard, located next door to the USS Constitution Museum . This ship has a fascinating story – it was commissioned as a warship in the early years of America’s independence to defend it from invaders and pirates. Learn all about it at this commemorative and interactive museum. 

Take a sunset cruise around Boston Harbor.

There’s nothing quite like seeing Boston from the water. Boston Harbor Cruises offers a 90-minute sunset cruise around the harbor. Embarking from the Wharf at 7pm, you’ll learn interesting facts about the Boston cityscape. And there’s nothing better than taking in the views at golden hour, it’s very romantic !

You can check out the best Boston boat tours here!

Visit the site of the Boston Massacre. 

In 1770, five people were shot and killed by British soldiers who opened fire in front of the Old State House . Today, you can visit this stop on the Freedom Trail . Take a guided tour of the Old State House to learn about Revolutionary history, and this building’s role in the Declaration of Independence.

 Explore the Museum of African American History.

A significant historical and cultural institute showcasing the lives and contributions of African Americans is found right in Boston: the Museum of African American History . With two preserved historic sites, two Black Heritage Trails, and permanent exhibits, you will learn all about black individuals and communities from the Colonial era through the 19th century.  

Go shopping on Newbury Street.

Boston has a lot of charming, quaint history, but it also has very fashionable and modern districts. If you love to shop, not many strips are better than Newbury Street in the upscale Back Bay neighborhood. From Anthropologie and Urban Outfitters to Ralph Lauren and Nordstrom, you will be surrounded by the latest apparel and beauty trends .

And Newbury Street is extra charming with shops set inside these historic brownstones. It’s especially cute decorated for the holidays!

Hang out with gorillas at the Franklin Park Zoo.

This 72-acre zoo in Boston is home to hundreds of exotic animals from around the planet. Franklin Park Zoo is the place to go if you want to encounter majestic creatures, such as a family of gorillas, ancient tortoises, and crocodiles. You will be supporting an institution that conserves, protects, and promotes better care of the natural world.

Visit the home of Paul Revere.

Interested in the history of the American Revolution? You can visit the home of one of America’s most significant Revolutionary figures, Paul Revere. This 1680 house still stands today, preserved and open for tours in Boston’s North End. Go learn about the cultural heritage of Paul Revere and his importance to the early days of Boston and America as a nation.

Read Next:  Top 20 Historic Sites in Massachusetts

Enjoy recreation and Revolutionary history at Castle Island.

Castle Island is one of Boston’s most valuable outdoor gems. This peninsula off the Harbor of Boston is connected to the Harborwalk, and has beautiful parks and paths for walking, biking, and picnicking along the beautiful beach.

This is also the site of Fort Independence, a granite bastion that defended Boston’s harbor as early as the American Revolution.

Discover booktopia at the Boston Public Library.

There’s something so satisfying about a good city library, and Boston definitely has a killer one. Boston Public Library in Copley Square is the oldest public library in America and has gorgeous Beaux-Arts and Renaissance style architecture. It feels like a Hogwarts-esque dream come true (plus free books!).

Stroll along the Charles River Esplanade.

Located right in downtown Boston is the beloved Charles River Esplanade . This beautiful 3-mile stretch of green space along the Charles River is rich in recreational opportunities. Along this pedestrian pathway made for strolling and biking, you’ll see fascinating monuments, great city views, boat launches, and grassy picnic areas.

Crack open a cold one at Samuel Adams Brewery. 

Bostonians love their beer, period. Samuel Adams reigns king in the city (Harpoon is a close second), so it’s only natural you stop by the Samuel Adams Statue and then try a brew at Samuel Adams Taproom . These light and refreshing beers are served on tap, with offerings of light fare to go with your drink. You will also be right near Faneuil Hall, the Old State House, and other fascinating sites. 

Take a stroll along the Harborwalk.

Boston Harborwalk is a public pathway that extends for 43 miles along the shore of Boston. Not only is the Harborwalk amazing for recreational activities, social gatherings, and picnic lunches, but it’ll give you amazing views of the city and ocean. Access it from multiple locations in the North End or Downtown to enjoy the wharves, beaches, piers, and benches as you stroll along. 

Read Next:  13 Best Walking Tours in Boston to Take

Take a Harvard University campus tour.

Want to explore America’s oldest college (established before America was even America)? Harvard University in Cambridge has an incredible campus for you to enjoy. With free public tours offered at the university, you can learn about Harvard’s history and wander the sprawling quads, historical buildings, multiple libraries, and museums. 

Visit the picturesque Beacon Hill neighborhood.

Dreaming of walking through a quaint, cobblestoned European town? Well, Boston has its very own neighborhood to make your dreams come true. Beacon Hill, one of the oldest neighborhoods in the city, is famous for its narrow cobblestone streets lined with federal style houses and lanterns. It feels like a magical fairytale, especially in autumn.

Don’t miss out on Acorn street, one of the best and most iconic photo spots in Boston. And be sure to step with care; those cobblestones are no joke!

Take a Boston beer tour.

Have people told you your eyes are bigger than your stomach? Well, you won’t be judged like that on a Boston Brew Tour . Embark on this 5-hour adventure to taste up to 16 different local brews at four different breweries. Enjoy entertainment, Boston beer history, transportation, and a deliciously paired meal at the end. Make sure to book your tickets in advance!

Hit the nightlife scene at Central Square.

Central Square in East Boston is an unsuspectingly happening neighborhood for nightlife. With everything from basement bars to clubs to fine dining and great music venues, this spot draws a youthful and lively crowd. Grab a pint at The Plough and Stars , then a gelato dessert at Toscanini’s , and when you’re finished catch a live show at The Middle East . 

Go ice skating at Canal District Kendall.

Formerly known as Kendall Square, Canal District Kendall in Cambridge is an innovative community with so much to do. There are green spaces, frequent outdoor live music events, and quality restaurants. But a local favorite is the large public ice rink that’s open for skating mid-December through mid-March. Bring your own skates or rent a pair. 

Read Next:  25 Ideas for a Wonderful Winter in Boston

Get spooked on a haunted ghost tour.

Because it is one of America’s first cities, Boston has some of the oldest cemeteries, buildings, and monuments in the nation. This makes for some captivating ghost stories; legends, haunts, mysteries, and myths are imbued in the very fabric of Beantown. If you love all things ghostly, why not take the Ghosts and Gravestones Trolley Tour ? Your costumed guides will share spooky stories as you roll through the creepiest locations. 

Chow down on Asian cuisine in Chinatown. 

Chinatown is a great neighborhood for foodies. This area of Boston is densely packed with a delectable variety of Asian cuisines. You can’t really go wrong no matter where you stop for dinner, but a few great selections include The Q for Chinese, Gourmet Dumpling House for dumplings, Pho Pasteur for Vietnamese, and RUKA for sushi.

Discover a secret store within a store. 

I bet you’ve never been to a store like Bodega ! This shoe and streetwear boutique is hidden behind a secret entrance that looks like a convenience store from the front. Upon closer inspection, you’ll find a backdoor that leads to the real Bodega, where the latest trends in sneakers, sportswear, and caps are waiting for you. 

Browse three floors of used books at Brattle Book Shop.

Boston is full of old things, and bookstores are no exception. Brattle Book Shop on West Street is one of the oldest and largest used book shops in the nation. This store has three whole floors of literary wonders. You’ll also find an excellent selection of magazines and some rare first editions.

Read Next:  10 Literary Sites in Boston All Book-Lovers Should Visit

Step inside a three-story globe.

Want something totally off the beaten path, and totally cool enough to land a spot in the Atlas Obscura? Located within the Mary Baker Eddy Library, the Mapparium is a three-story globe you can walk through! This map is a beautiful glowing orb that provides a unique experience for visitors, and the library that houses it is also worth a look.

Indulge in Cannoli at Mike’s Pastry or Modern Pastry.

Boston’s #1 Cannoli war rages on in the North End, the city’s “Little Italy.” Is it Mike’s Pastry , or Modern Pastry? Well, we don’t see why we have to choose one or the other, so let’s just eat both! Mike’s typically has longer lines but heftier portion sizes and a greater flavor variety. Modern Pastry is less mobbed and has a richer cream filling, but a smaller cannoli.

Read Next:  Where to Find the Best Cannoli in Boston

Drink a cappuccino at Caffe Vittoria, the first Italian cafe in Boston.

Andiamo! Caffe Vittoria in the North End was established in 1929, making it Boston’s first Italian cafe. This beloved local coffee shop has four floors filled with vintage Italian decor, a coffee bar, and all the best drinks that you could find in Italy.  I adore this place!

Read Next:  13 Best North End Restaurants in Boston

Shop local at Boston Public Market.

Found at Haymarket Station is Boston Public Market , an expansive year-round indoor marketplace. This community space consists of over 30 New England artisans, farmers, and shop owners selling fresh foods, crafts, and locally sourced meals. Shopping here not only allows you to experience the tastes and creations of New Englanders, but it helps uplift small businesses. 

Kayak on the Charles River.

Love that dirty water! Charles River is a local favorite for recreational adventures. This river extends for 80 miles and cuts right through the city. You can rent kayaks, canoes, or paddleboards from Charles River Canoe and Kayak and either take a guided tour along the Charles River or embark on your own solo adventure. 

Witness oddities at the Warren Anatomical Museum.

If you like museums but also want to see something out-of-the-box, visit the Warren Anatomical Museum at Harvard. This anatomy and pathology museum was started in the 1800s by a Harvard anatomist to preserve specimens for student education. You will find oddities like an old plastic surgery kit, eagle skeletons, and the actual skull of Phineas Gage. 

Read Next:  50 Wicked Awesome Quotes About Boston

Visit a skinny house built out of spite .

Skinny House, or “Spite House,” is a 10-foot-wide, four-story home at 44 Hull Street. Squeezed between two brick facades, this is known as the narrowest in Boston. Legend has it that during the Civil War, it was built out of spite by a soldier to get revenge on his brother. Being left with only a small piece of their land inheritance after his brother built a massive home on it, the skinny house was built to block his brother’s views and sunlight.

Read Next:  15 Unique Boutique Hotels in Boston to Book in 2023

Go island hopping at Boston Harbor Islands State Park.

Boston Harbor Islands State Park is a New England coastal gem. Just one mile from the city center, this oceanic park is a collection of 34 islands and peninsulas that can be accessed by a park ferry. But the ocean isn’t the only thing you’ll see amongst these islands; you can also visit one of the historical forts, mainland parks, or the Boston Lighthouse.

Have breakfast at Trident Booksellers & Cafe.

Books are even more wonderful when paired with good coffee and a meal. Trident Booksellers & Cafe offers this match made in heaven. Part-bookstore, part-coffee shop, a visit to Trident will come complete with the latest bestsellers and classics. Not only is it a fantastic independent book store, but the breakfast is fantastic. My monte cristo sandwich and French toast latte were one of the best meals I’ve had in Boston.

Join the community fun at Harvard Square.

Want to see what locals are doing for fun in Cambridge? Harvard Square is where it all comes to life. There are events taking place in and around this large triangular plaza almost every day of the week. Listen to live music, attend author readings at Harvard Bookstore, go on a chocolate tour, or even join in on a beginner’s Tai Chi class. This is one hopping corner of Boston. 

You might also like:

• The 10 Best Things to Do in Boston for First Timers
• Things to Do for Christmas in Boston
• 10+ Best Day Trips from Boston
• The Ultimate Guide to St Patrick’s Day in Boston
• Where to Go for the Best Breakfast in Boston
• Boston Slang: 30 Wicked Cool Boston Sayings You Should Know!
• Spring in Boston: 12 Best Things to Do for Spring Fun

5 charming New England towns you can drive to from Boston

Update: Some offers mentioned below are no longer available. View the current offers here .

While a typical summer weekend in Boston usually means a stroll along the Charles River or a picnic in the Common, we all know this summer won't be anything close to normal.

Travelers who need a change of scenery can find charming New England towns and untouched stretches of wilderness just a few hours from the city.

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From Boston , travelers can reach many exciting and overlooked destinations, such as the vertical granite cliffs of Camden Hills State Park and historic towns filled with lovely Victorian homes. If you're planning on spending more time in the great outdoors than ever before, there are plenty of opportunities for adventure-fueled days spent rock-climbing, hiking and kayaking.

Related: 6 of the best-value points hotels in Boston

Whether you're planning a road trip from Boston this summer or a year from now, remember that small New England towns are filled with intimate B&Bs and historic inns, be sure to book with a credit card that will help you maximize your travel purchases, such as the Chase Sapphire Reserve® (3x) or Chase Sapphire Preferred® Card (5x when booked through Chase Ultimate Rewars,2x on all other).

Related: Going on road trips this summer? Consider using these credit cards

And be sure to keep a great card for earning points on gas purchases in your wallet, too — especially if you're driving three hours or more outside Boston. With the Citi Premier® Card, you'll earn 3x points per dollar when you fill up at gas stations, along with 3x points on air travel, hotels, restaurants, and supermarkets and 1 point per dollar on everything else — ideal for a long weekend exploring New England, staying in charming inns and eating as much clam chowder as you can stomach.

If you're planning a near-term road trip, just remember that many states may still require out-of-state travelers to self-quarantine for two weeks. Maine's executive order , for example, requires a 14-day self-quarantine for visitors through much of the summer. Plus, many inns, restaurants and attractions may remain closed, at least to out-of-towners. So, you might want to bookmark these itineraries for later.

Related: 10 tips for anyone taking a road trip right now

Camden, Maine

Distance from Boston: 3 hours and 20 minutes

Often overshadowed by nearby Bar Harbor , Camden is a haven for outdoorsy travelers. Sure, visitors can spend an afternoon wandering up and down Main Street, stopping to admire the views of Camden Harbor or peruse the boutique shops (be prepared to spend too much on unexpected finds at Josephine on Elm Street). But to make the drive — just over three hours — worthwhile, travelers should take advantage of the destination's ample outdoor activities.

What to do : Explore Camden Hills State Park on the 30-mile trail network. One of our favorites is the moderate trail up to Ocean Lookout for an uninterrupted view of the town and harbor. If you're interested in something more, well, vertical, have Equinox Guiding Service bring you out for an afternoon of rock climbing. For a more relaxed option, head out to Savage Oakes Vineyard and Winery to sample their house blends, made with 10 grape varieties grown on-site.

Where to stay : Camden has a mix of lodging options, mostly small bed and breakfasts and inns. But 16 Bay View is Camden's newest luxury hotel, housed in a 100-year-old industrial brick building that once operated as a car dealership. For a more intimate stay, book a room at the Camden Harbour Inn , with rooms and suites that boast (as its name implies) exceptional views of the water.

What to eat and drink: Located in the Camden Harbour Inn, travelers should reserve a table on the porch of Natalie's Restaurant . If oysters are what you're after, head over to 18 Central Oyster Bar and Grill , in nearby Rockport, for a platter of their local or "away" raw oysters.

Related: Why you should visit Acadia National Park in Maine

Freeport, Maine

Distance from Boston : 2 hours

While Freeport is best known as the birthplace of LL Bean, there are plenty of other reasons to spend a weekend in town. Located just north of Portland on the shores of Casco Bay, brick buildings line Freeport's streets, and shoppers wander unhurried between the outlet stores and seafood-centric restaurants.

What to do : Start your trip to Freeport by stocking up on activewear and outdoor gear at LL Bean's flagship location, which is typically open 24 hours every day. Shoppers should also check the outlets at the Freeport Village Station. Just be sure to keep a great card for everyday spending , such as The Blue Business® Plus Credit Card from American Express or the Chase Freedom Unlimited, in the front of your wallet. Afterward, head over to DeLorme, in nearby Yarmouth, to see the world's largest rotating globe (it's nearly 42 feet across), or take a walk through the hemlock and white pine forests of Wolfe's Neck Woods State Park .

Where to stay : The Brewster House Bed and Breakfast is an upscale inn just three blocks from the center of Freeport. Seven rooms and suites make this a great choice for a romantic getaway, or for families exploring coastal Maine. Another option is the Harbour Towne Inn on the Waterfront — a Victorian-style bed and breakfast with panoramic views of Boothbay Harbor.

What to eat and drink : Start the morning with a cup of the daily roast from Coffee By Design , a sustainable cafe located inside the LL Bean store. Linda Beans is a favorite for seafood (order the classic Maine lobster roll) right on the main strip. Outdoor seating with fire pits makes this a great spot during cool, early summer evenings. Visitors should also sample Maine Distilling 's Blueshine blueberry liquor when the distillery is open for tastings.

Related: The 7 best 'secret' swimming holes to visit this summer

Stockbridge, Massachusetts

Surrounded by the mountainous terrain of the Berkshires , Stockbridge is a small town in rural Massachusetts with the culture and arts scene of a big city — with none of the traffic or crowds. Summers are usually filled with music festivals and theater, and travelers can also explore the area's extensive hiking and biking trails.

What to do: Founded in 1934, the Berkshire Botanical Garden (closed until further notice) is a 15-acre public garden that showcases local flora alongside contemporary sculpture exhibitions. Need a more strenuous activity? The Laurel Hill Association maintains three hiking trails in the Stockbridge area — the Mary Flynn Trail, Laura's Tower Trail and Ice Glen Trail. After a day of hiking or strolling through the gardens, travelers can typically catch an opera or theatrical performance at the historic Mahaiwe Performing Arts Center (closed until further notice). And, if you have the time to dedicate during your weekend trip, head to the Kripalu Center for Yoga and Health (closed for the remainder of 2020), a retreat offering a mix of yoga, writing and Ayurveda courses, among others. Programs typically last for at least two days.

Where to stay: The Stockbridge Country Inn is located within walking distance of multiple area museums. Its location on four acres of manicured lawns and gardens, complete with a patio and heated outdoor pool, make it a great place to relax and enjoy a hot summer afternoon. The Inn at Stockbridge is another option, with 15 rooms spread throughout a renovated barn, a Victorian-style mansion in which many original antiques remain and a cottage house. When Miraval finally welcomes visitors to its third resort in the Berkshires , guests can focus on wellness and mindfulness. After all, it wouldn't be a Miraval resort without a full spa experience. Miraval resorts occupy their own lane in the World of Hyatt award chart, and a free night will cost you 45,000 points, plus an additional 20,000 per night for an additional guest in your room.

What to eat and drink: Providing food and accommodations to visitors for over two centuries, The Red Lion Inn serves traditional New England cuisine (along with an expansive wine list featuring over 400 different selections). For classic European dishes (think: escargot pot pie), try Once Upon a Table , which also dishes up more hearty, regional fare (crab cakes, for example).

Related: 4 incredible fall foliage drives in the Northeast

Woodstock, Vermont

Distance from Boston : 2.5 hours

Located in the heart of the Green Mountains, Woodstock is the quintessential New England town. New openings and upgrades over the past few years have transformed this drive-by town into a popular (and rather upscale) getaway for New Englanders. A pedestrian-friendly downtown is filled with small shops, inns and restaurants, while the surrounding rural landscape invites visitors to explore and unwind.

What to do : As the Northeast's premier skiing destination during the winter months, many of Vermont's ski resorts are overlooked as soon as the snow melts. For this reason, the local ski hill, Suicide Six, has a new mountain bike park, which has miles of machine-built trails that are free to use. If extreme sports are not for you, take a tour of the Billings Farm & Museum when it reopens (you'll get a firsthand look at what farm-to-table actually means). Woodstock and the surrounding hills are also great for cross-country cycling. Travelers will discover rural roads that meander along streams and past historic farmhouses. Before driving back to Boston, drop by the farmer's market to stock up on fresh snacks.

Related: Attractions worthy of a family road trip in Vermont

Where to stay: The Woodstock Inn and Resort has 142 traditional rooms and suites that mix history (like handmade furniture) with modern amenities (think: Wi-Fi, Nespresso machines and flat-screen televisions). Located about nine miles from Woodstock in Barnard, Twin Farms is an exclusive five-star resort spread across 300 acres. The all-inclusive has a renowned culinary program — and a price tag to match.

What to eat and drink: With thousands of farms in the state of Vermont, food in the Green Mountain state is incredibly fresh. Worthy Kitchen , for example, has a rotating menu based on what's in season, as well as a beer list that showcases some of the state's finest craft breweries, including Hill Farmstead and the Alchemist. At Soulfully Good Cafe , visitors can try the signature cream apricot scones for a sweet breakfast on-the-go.

Related: Use your points and book a staycation at one of these 7 kid-friendly resorts

Narragansett, Rhode Island

Distance from Boston: 1.5 hours

This coastal Rhode Island town is a classic New England beach destination, with four of the state's arguably most popular beaches nearby. Visitors will get their fill of local seafood while exploring the oceanfront, or venturing to nearby Block Island or Newport .

What to do : Situated on 60 acres of state parkland, The Scarborough State Beach boasts more than 2,000 feet of sandy ocean frontage and is home to a newly renovated pavilion. Narragansett Beach may be one of the best on the East Coast, and if lighthouses and history are your thing, visit the historic Port Judith Lighthouse, which was first constructed in 1806. The Towers, or Twin Towers, is another landmark structure, and it's the only remnant of the Narragansett Pier Casino, which was the heart of Narragansett during the late 19th century. Today, the restored Towers typically host an assortment of events, including dance lessons and musical performances.

Related: 5 ways to explore Newport this summer

Where to stay : Many of the rooms at the Aqua Blue Hotel have full or partial ocean views (and balconies), and it's centrally located in town. There are also several bed and breakfasts, such as the Ocean Rose Inn , which overlooks Newport Harbor, Narragansett Bay and Jamestown Island. Eighteen new rooms were revealed in 2017 as part of a property renovation.

What to eat and drink : Built in the late 1800s by the U.S. Coast Guard, this granite structure is now home to the Coast Guard House , a seafood restaurant perched on Narragansett Bay. If you overslept, head to Crazy Burger (hear us out). In addition to an eclectic vegetarian-friendly menu with items like the Poco Loco Vegan Burger, the restaurant usually serves breakfast until 4 p.m. daily.

Additional reporting by Melanie Lieberman.

The Perfect 7-Day New England Road Trip from Boston 2024

Planning a 7-day New England road trip itinerary from Boston?

Ah, New England. I have long been smitten with this historic region of the country, which includes Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont.

Now that I’ve lived in New England for five years, I have a better understanding of the BEST places to see if you’re visiting for a short time.

Once you arrive in New England, you will likely wish you could stay much longer than 7 days. However, there are several highlight spots you can reach in one week to get a good taste of the region. That’s the list I have curated for you in this 7-day New England road trip itinerary!

⏰ SHORT ON TIME? 🛌 DESTINATIONS + WHERE TO STAY Boston, Massachusetts: Hyatt Regency Boston Harbor Newport, Rhode Island: Hotel Viking Mystic to Washington, Connecticut: Mayflower Inn & Spa Stockbridge, Massachusetts to Killington, Vermont: Mountain Meadows Lodge Stowe, Vermont: Trapp Family Lodge White Mountains, New Hampshire: New England Inn & Lodge Portland, Maine and Portsmouth, New Hampshire: Hampton Inn & Suites 🚗 NEED A CAR? Book through Discover Cars for some of the best rates

New England Road Trip for 7 Days

This road trip is a loop that begins and ends in Boston, Massachusetts, the largest city in New England. If you plan to fly to New England and rent a car there, you can usually find the best flight deals into Boston.

From Boston, you’ll travel south to Rhode Island and Connecticut, north through western Massachusetts and into Vermont, northeast into New Hampshire and Maine, and then back down to Boston.

• Day 1: Boston, Massachusetts

Kick off your 7-day New England itinerary with a tour of Boston. Explore North End , Boston’s Little Italy, to taste authentic Italian food, and then begin walking along the historic Freedom Trail by Old North Church .

Stop by Faneuil Hall Marketplace , known as the Cradle of Liberty because patriots would meet here in the days leading up to the Revolutionary War. Not far from Faneuil Hall you can also see Boston’s Old State House, Old South Meeting House , and the Benjamin Franklin statue.

Have lunch in Boston’s Chinatown , a center of Asian-American life in New England. Then walk over to Copley Square and explore the beautiful Boston Public Library (don’t miss Bates Hall!).

Browse the shops along Newbury Street before walking the Charles River Esplanade for scenic city views. End your day in Boston by exploring the picturesque cobblestone streets of Beacon Hill and walking through Boston Common and the Public Garden .

🇺🇸 For a fun way to learn about the history of Boston, check out this popular walking tour with an emphasis on storytelling .

➡️ See my 24 hours in Boston post for a more detailed list of things to do in Boston in a day, along with a sample route map.

Where to Stay in Boston

📍 Hyatt Regency Boston Harbor : Mid-range hotel with great views of the Boston Harbor.

📍 Omni Parker House : One of Boston’s most iconic and historic hotels, in operation since 1855.

• Day 2: Newport, Rhode Island

Only 1.5 hours south of Boston is the beloved coastal town of Newport, Rhode Island . It’s my husband and my favorite place in Rhode Island and one we never get tired of visiting.

The best thing to do in Newport is walk the scenic Cliff Walk , a 3.5-mile scenic trail with stunning views of the Atlantic Ocean almost the entire way. While you’re near the Cliff Walk, it’s also worth stopping by one of the iconic Newport mansions for a tour. The most famous of the mansions is The Breakers .

Book this five-star-rated Newport trolley tour for an easy way to tour the Breakers and see other key sites in Newport. ⭐️⭐️⭐️⭐️⭐️

Downtown Newport, especially Thames Street, is bustling with shops and restaurants within traditional New England architecture. The Red Parrot restaurant has delicious fish and chips, but if you want to visit the oldest operating restaurant in the U.S., go to White Horse Tavern .

🦀 Want to experience more of Newport’s food scene? Check out this highly-rated food and history walking tour .

After that, it’s worth stopping by Kilwins for ice cream and enjoying it on a bench in Queen Anne Square while looking out at Newport Harbor .

If you have time to spare, hop on the Newport Harbor Shuttle to Fort Adams State Park and take a walk around the old fort for beautiful water views.

Where to Stay in Newport

📍 America’s Cup Inn : A small hotel within easy walking distance of most downtown Newport attractions. Each room is uniquely decorated with antique, colonial furnishings.

📍 Hotel Viking : On the list of Historic Hotels of America, this hotel is full of character and charm.

Day 3: Mystic to Washington, Connecticut

On day 3 of this 7-day New England road trip, you will head one hour west to the moody port town of Mystic —one of Connecticut’s most beautiful places .

Here you will find one of the largest maritime museums in the United States, Mystic Seaport, as well as the oldest merchant vessel in the U.S., the Charles W. Morgan whaleship.

The main street of Mystic has several cute boutique shops and restaurants. If you’re craving seafood, you might enjoy The Mariner for a tasty lunch. Their menu ranges from oysters and clams to fish and lobster.

If you’re a book lover, it’s worth visiting the Book Barn in Niantic for an hour or two. It’s one of the largest used booksellers in New England with more than 500,000 books, and it’s only about a 25-minute drive west of Mystic.

From there, you will drive about 1.5 hours northwest to the charming town of Washington, Connecticut .

Park near the old post office, which is now the popular Po Cafe serving delicious food and drinks. (Note they are only open until 2 p.m. and are closed on Sunday and Monday, so I suggest coming here for breakfast on Day 4.)

Not far from the cafe, you can walk past the picturesque First Congregational Church , a large white-steepled church typical of New England, and then stroll through the quiet neighborhoods with their quaint, well-landscaped homes.

Where to Stay in Washington

📍 A Whimsical Cottage : This cozy vacation home will give you a more local experience of Washington.

📍 Mayflower Inn & Spa : If you’re a Gilmore Girls fan, this luxurious hotel will be especially meaningful, as it’s said to have inspired the Independence Inn on the show.

• Day 4: Stockbridge, Massachusetts to Killington, Vermont

Start your day with breakfast at the Po Cafe in Washington before heading north to the historic town of Stockbridge, Massachusetts , located in the scenic Berkshires highlands.

Inside the old Stockbridge General Store building is  Main Street Cafe , which still maintains a lot of the original interior. The old general store was made famous in one of Norman Rockwell’s paintings.

Speaking of Norman Rockwell, the Norman Rockwell Museum is also located in Stockbridge, if you want to see some of the original artwork from the iconic American painter.

After spending some time in Stockbridge, you’ll continue driving a little over two hours north into the lush Green Mountains of Vermont.

If you’re up for a hike after all that driving, you could do the moderate 2-mile out-and-back Deer Leap Overlook Trail near Killington, which takes just over an hour to complete.

Finish the day with a hearty dinner at Casey’s Caboose or The Garlic , both located in Killington.

Where to Stay in Killington

📍 Mountain Meadows Lodge : Cozy rooms and delicious breakfast, with gorgeous mountain views.

📍 The Snowed Inn : Close to Killington ski resort, this hotel has a year-round outdoor hot tub.

• Day 5: Stowe, Vermont

On day 5 of this 7-day New England road trip, you will visit the magical town of Stowe, Vermont .

About an hour and 20 minutes north of Killington, Stowe is known as the birthplace of alpine skiing in Vermont. Its first lift-operated ski run began in 1937 on Mount Mansfield (the tallest point in Vermont at 4,939 feet).

However, Stowe is great to visit any time of the year. In the fall, tourists flock here for some of the best fall foliage vistas in New England. Spring is the perfect time to go on a maple syrup tour to learn how Vermont’s famous sugary goodness is made.

In the fall, spring or summer, enjoy one of Stowe’s many hiking and biking trails or kayak along the Winooski or Lamoille Rivers .

Best hiking trails in Stowe

• Stowe Pinnacle via Pinnacle Meadow Trail (Moderate): This 3.2-mile out-and-back trail takes about two hours to complete and connects with the popular—but more challenging—Stowe Pinnacle Trail that leads up to Stowe Pinnacle.
• Bingham Falls Trail (Easy): This 0.5-mile out-and-back trail only takes about 20 minutes to complete and provides lovely views of Bingham Falls at the end. People have commented that the rocks can get slippery near the bottom, so be careful!
• Stowe Recreation Path (Easy): This paved 5.5-mile, out-and-back greenway is great for bikes and strollers. There are numerous shops and restaurants along the path where you can stop to browse or grab a bite to eat.

Other things to do in Stowe

• Visit Moss Glen Falls located along the scenic VT 100 highway.
• Tour Smugglers Notch State Park and drive the VT 108 highway.

Where to Stay in Stowe

📍 Green Mountain Inn : Rooms decorated in handcrafted Vermont furnishings, located in the center of historic Stowe.

📍 Trapp Family Lodge : Austrian-inspired architecture and furnishings with gorgeous mountain views.

• Day 6: White Mountains, New Hampshire

Now that you’ve experienced the Green Mountains of Vermont, drive a couple hours east to the White Mountains of New Hampshire .

Start in the small town of Lincoln, where you will find the beginning of the famous Kancamagus Highway , a scenic 34.5-mile drive through White Mountain National Forest. There are numerous stops along the highway for stunning outlooks and hiking trails:

• Lincoln Woods Trail: This is one of the first stops along the Kancamagus Highway. Walk the suspension bridge over the rocky Pemigewasset River and you’ll end up on a leisurely out-and-back trail along the river with towering trees overhead.
• CL Graham Wangan Overlook: From this point, you will have one of the prettiest views of the Swift River Watershed and White Mountain peaks in the distance.
• Sabbaday Falls: A short hike will lead you to this beautiful waterfall, which has a guardrail on one side for you to stand and see the falls up close. There is a picnic area nearby, making for a picturesque spot to enjoy lunch.
• Sugar Hill Overlook: This is one of the most popular viewpoints along the Kancamagus Highway, where you can see the Swift River Valley and surrounding mountains.
• Rocky Gorge: Take the small footbridge across the gorge for scenic views of the Swift River.
• Albany Covered Bridge: See one of New England’s traditional covered bridges right along the Kancamagus Highway.

The Kancamagus Highway ends near North Conway, where you can enjoy a laid-back, all-American meal at the highly-rated Muddy Moose Restaurant & Pub or Delaney’s Hole in the Wall .

Where to Stay in North Conway

📍 New England Inn & Lodge : Comfortable and cozy rooms in a wood cabin-style hotel.

📍 White Mountain Hotel & Resort : Features a heated pool and hot tub overlooking the mountains.

Day 7: Portland, Maine and Portsmouth, New Hampshire

On the last day of this 7-day New England road trip, head 1.5 hours southeast to the iconic coastal town of Portland, Maine . Here you will see a blend of traditional New England architecture and history, along with contemporary, artsy vibes.

Visit Bug Light Park to see the beloved Bug Light, standing at only 26 feet tall, and walk along the scenic Eastern Promenade for stunning views of Casco Bay.

Take a ride on the historic Maine Narrow Gauge Railroad , and snag some fresh seafood from the Portland Farmer’s Market (open Wednesdays and Saturdays) or Harbor Fish Market .

The #1 thing to do in Portland is visit America’s most photographed lighthouse, Portland Head Light , located on Cape Elizabeth. Not only is the lighthouse itself beautiful, but the surrounding landscape will take your breath away.

The very last stop on this 7-day New England road trip is Portsmouth, New Hampshire , another picture-perfect town about an hour from Cape Elizabeth.

Park downtown and browse the shops and boutiques along Congress Street. For dinner, I highly recommend The Flatbread Company , which makes delicious wood-fired pizza with locally sourced ingredients.

Where to Stay in or near Portsmouth

📍 Hampton Inn & Suites : Centrally located in Portsmouth with breakfast included, this hotel is a short walking distance from restaurants and other town attractions.

📍 Wentworth by the Sea : Located in New Castle, just outside of Portsmouth, this dreamy hotel offers cozy rooms with stunning harbor views. I’ve stayed here a couple of times and absolutely loved it.

New Castle is less than an hour from Boston, where you can return on Day 8 to end your epic New England road trip!

New England 7-Day Road Trip Map

More Places to Add to Your Itinerary

If you want to extend your trip beyond a week (I would not blame you one bit), here are a few other places to add to your itinerary!

Acadia National Park, Maine

The crown jewel of the North Atlantic coast, Acadia National Park is an absolute must-see. I didn’t include it in this 7-day New England itinerary because it’s a bit too far north, but if you have a few more days to spare, you won’t regret a visit here.

Reserve a time slot on Recreation.gov to take in the mesmerizing views at the summit of Cadillac Mountain (note the Cadillac Mountain Summit Road is only open from around April to October).

Relax on one of Maine’s only sandy beaches, aptly named “ Sand Beach ” and walk along the jagged coastline on the Ocean Path Trail .

Hike around Jordan’s Pond and try the famous tea and popovers at Jordan’s Pond House Restaurant .

And of course, you must pay a visit to the picturesque town of Bar Harbor , right next to Acadia National Park. Jordan’s Restaurant is known for its amazing blueberry pancakes, and Mount Desert Island Ice Cream serves some of the most interesting flavors.

How to incorporate Acadia National Park into your New England itinerary:

Acadia National Park would naturally fit after Day 6 in this itinerary, but you would want to give yourself at least three extra days to drive up there and fully explore the region before heading south to Portland.

Ogunquit, Maine

Ogunquit is a popular destination here in New England but not as well-known in other parts of the USA. It’s one of the first towns after crossing the border into Maine, and it has a lot of fun things to do.

• Ogunquit Beach Lobster House : Not far from Ogunquit Beach, this restaurant serves amazing seafood. This is the place where I first fell in love with lobster rolls.
• Ogunquit Beach: This family-friendly beach is especially popular in the summer as it’s a large beach and there are many shops and restaurants nearby.
• Perkins Cove: Browse through this cluster of shops and restaurants in traditional New England architecture. Be sure to stop at the Corner Cafe for delicious Maine blueberry pie ice cream!
• Marginal Way: Near Perkins Cove is Marginal Way, a 1.25-mile trail with ocean panoramas the entire way. It gives the Cliff Walk in Newport, RI a run for its money.

How to incorporate Ogunquit into your New England itinerary:

You could swap Portsmouth, NH with Ogunquit, ME on Day 7 and visit Portsmouth on Day 8, OR dedicate an entire day to Portland, ME and spend Day 8 in Ogunquit and Portsmouth.

Salem, Massachusetts

Salem is best known as the location of the Salem Witch Trials in 1692. If you are curious about the town’s dark past, visit the Salem Witch Museum , Salem Witch Trials Memorial , and Old Burying Point Cemetery . Unsurprisingly, Salem is especially popular to visit during the Halloween season.

The House of Seven Gables , made famous by Nathaniel Hawthorne’s 1861 novel with the same name, is also located in Salem and worth a tour.

How to incorporate Salem into your New England itinerary:

Stay an extra day in Boston and visit Salem as a day trip. Salem is only about 25 miles north of Boston.

Cape Cod, Massachusetts

For beautiful New England architecture, bright and blossoming hydrangeas, and some of Massachusetts’ best beaches, visit the state’s iconic curved peninsula, Cape Cod. It’s one of Massachusetts’ most popular destinations, and with good reason.

Cape Cod is busiest in the summer months when New Englanders and out-of-towners flock to the beaches. If swimming isn’t your #1 priority, you might choose to visit in the spring or fall instead.

Coast Guard Beach is one of the best beaches on Cape Cod, but Keyes Memorial Beach is also a good option. If you have time to drive all the way to the tip of Cape Cod, the town of Provincetown is known for its art galleries and delicious restaurants.

How to incorporate Cape Cod into your New England itinerary:

Extend this 7-day itinerary by another day or two (or longer, if you plan to visit Martha’s Vineyard or Nantucket as well!).

Martha’s Vineyard or Nantucket, Massachusetts

In many ways, the iconic islands of Martha’s Vineyard and Nantucket represent what people traditionally associate with New England: wind-weathered, shingled homes, harbors filled with sailboats and seagulls, and quaint shops and restaurants. A visit to one of these islands will make you feel like you escaped to another world.

How to incorporate these islands into your New England itinerary:

I recommend visiting Cape Cod and one or both of the islands at the same time, as one of the best ferry options to the islands departs from Hyannis or Woods Hole on Cape Cod.

The ferry ride from Hyannis to Nantucket is roughly one hour, and from Woods Hole to Martha’s Vineyard is about 45 minutes.

Lake Champlain and Burlington, Vermont

Lake Champlain is Vermont and New England’s largest lake, which is also shared with New York and Quebec, Canada. There are plenty of things to do on and around the lake, including boating, kayaking, swimming, shopping, dining, and more.

Burlington is the largest city in Vermont and is nestled right along Lake Champlain. It’s a hip, artsy town with an awesome food and shopping scene.

How to incorporate Lake Champlain into your New England itinerary:

An extra day or two to visit Lake Champlain and Burlington could be sandwiched between Days 5 and 6 in this New England itinerary.

Here are answers to some common questions about New England.

When is the best time to visit New England?

This all depends on what interests you most! New England is beautiful any time of the year, but winter is the most unpredictable in terms of weather. It’s not uncommon for there to be large snow storms that make travel conditions especially difficult.

Unless you are going with the intention of skiing in Stowe and doing other winter activities, you may want to avoid a road trip to New England from December to mid-March.

Do you enjoy exploring in the winter? Check out Massachusetts in Winter: Things to Do, Places to Visit, and More .

Spring is beautiful in New England with all the blossoming trees, but expect a little more rain than usual from March to June. Some hiking trails might still be muddy from the rain and melting snow.

New England summers are really nice, with warm temperatures that are typically not overbearing and lots of sunny days. July to September is when spending time at the beaches and lakes is the most enjoyable.

Of course, New England attracts lots of tourists in the fall because of the colorful foliage. What’s also great about this time of year is the temperatures are a bit cooler but still pleasant enough for hiking and sightseeing.

When is the best time to see fall foliage?

This can be tricky to say, depending on which part of New England you visit and what the weather is like.

For example, in 2022, we visited the White Mountains of New Hampshire in mid-October and already missed the peak period for colorful foliage . At the same time, the leaves were only just beginning to change color in Boston where we live.

For northern New England states, including Vermont, New Hampshire and Maine, the end of September to the beginning of October will likely be the best time to see the fall colors.

For southern New England, including Massachusetts, Connecticut, and Rhode Island, peak season will likely be a bit later, from the beginning of October to early November .

For some of the best fall foliage sightseeing in New England, check out 10 Best Stops on the Kancamagus Highway, New Hampshire .

How many days do I need in New England?

As you have probably gathered from this post, there is A LOT to see in New England. 🙂 At a minimum, I recommend spending an entire week in this region to get a taste of all six New England states.

However, if you have a little more time to spare, two weeks would allow you to tack on additional destinations not included in this 7-day road trip, such as Cape Cod or Acadia National Park.

Is New England expensive?

This varies based on what time of year you go and what activities you want to do. Generally, costs in New England are a bit higher than other parts of the U.S. but as with any trip, there are ways to spend more money and ways to save.

For example, if you plan to spend the majority of your time hiking and walking outdoors, your trip will not be nearly as expensive as if you book a lot of special tours and activities or often dine in restaurants.

Tourism in New England is highest in the summer and fall, so hotel costs will likely climb during these seasons.

New England is such a historic and beautiful part of the country, with something for everyone to enjoy. To recap, here is a quick summary of this 7-day New England road trip:

• Day 3: Mystic, Rhode Island to Washington, Connecticut
• Day 7: Portland, Maine to Portsmouth, New Hampshire

If you’ve determined that New England is too awesome to limit your visit to just one week, here are some great add-ons:

• Acadia National Park, Maine (between Days 6 and 7)
• Ogunquit, Maine (on or after Day 7)
• Salem, Massachusetts (between Days 1 and 2 or after Day 7)
• Cape Cod, Massachusetts (after Day 7)
• Martha’s Vineyard or Nantucket, Massachusetts (after Day 7)
• Lake Champlain, Vermont (between Days 5 and 6)

Have a fabulous time!

PLANNING A TRIP? These are the resources I recommend: ✈️ Flights:   Skyscanner 🛌 Hotels:  Booking.com ​ 🚗 Rental cars:   DiscoverCars 🎟 Tours: Viator  or  GetYourGuide

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New England Wanderlust

Connecticut , Fall , Maine , Massachusetts , New Hampshire , Rhode Island , Vermont  ·  June 7, 2023

The PERFECT New England Fall Road Trip Itinerary: 3, 5, 7, 10 & 12 Day Options! (2024)

There’s a reason why New England is world-famous for fall foliage, and if you’re looking to plan the most amazing New England fall road trip, you’ve come to the right place! I’ve been traveling throughout this region for over 15 years, and have done quite a few fall foliage road trips and even more fall getaways. It took me a while, but I’ve finally put together the perfect itinerary for you based on real experience.

This post details the best places to visit in New England during fall foliage season that are worth the hype, the best times to plan your road trip, and also, which places may not be worth your time. So, you can rest assured that you’re truly seeing the best of the best with my itinerary.

This itinerary is also geared toward first-timers and those looking to find the best foliage spots . If you’ve experienced New England in the fall season before, many of these locations and tips may already be familiar. However, I’ve also sprinkled in some insider tips, so it’s still definitely worth reading 😉

During this trip, prepare to see idyllic countryside landscapes, blazing fall color, beautiful covered bridges, charming towns, general stores, epic overlooks and hiking trails, and so much more. Basically, you’ll get your fill of New England charm right from the start, and it won’t stop until the trip is over. Sound good? Then let’s get started!

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 .

Tips For Planning A Trip To New England In The Fall

There are some important things to know before you begin to plan your perfect New England fall road trip, so let’s get that out of the way first 😉

The first thing you need to know is that foliage will peak in the northern areas first, then peak in the southern areas later . For that reason, I recommend that you start in the north if you can, especially for a longer trip, but it’s not always necessary for shorter trips.

If you’re planning a bucket list 2-week adventure, starting in the north is a good call because peak foliage can begin to diminish quickly, depending on the season and climate patterns. However, if you’re traveling for closer to a week, this won’t be as important.

I go into peak foliage times in each region in a bit, so definitely be sure to read that through, too!

Another important thing to know is that you should anticipate all kinds of weather. I’ve done many fall road trips through this region, and have had warm, sunny days, and trips where it rained almost every single day. I’ll go more into what to pack for this trip at the end of the post to help you prepare, but this is a good thing to be aware of.

Also, book in advance . I can’t stress this enough. Hotels and accommodations book out well in advance for fall foliage season in prime areas, and these prime areas are where you’ll be heading! If possible, begin to book your hotels at least 6 months in advance, but even 8 months is better. For reference, while I began to plan my Vermont fall road trip for the 2023 season, my favorite place to stay in Stowe, VT was fully booked during peak foliage weeks – in FEBRUARY. Yep, February.

Offline Google Maps! I can’t tell you how important this is! Even as recent as a fall 2022 road trip, I barely had service through much of New Hampshire and Vermont. I spent a lot of time just driving around hoping my service would come back, or asking people for directions the old-fashioned way. I usually offline maps, but totally forgot that trip, and it was a harsh reminder that this is a must-do.

Lastly, prepare to pay . Yes, the sad truth is that peak foliage season in New England is expensive, and it won’t be your most budget-friendly trip ever. There are ways to keep costs down, and I’ll go more into that later in the post as well, but generally speaking, this is an expensive time to visit New England – at least, where the foliage is the best 😉

What Is The Best Time To Visit New England For Fall Color?

In a nutshell, the last week of September, or the first week of October. However, it does vary depending on where you’re heading.

As mentioned before, the colors will begin to change in the northern regions first, and then the southern regions will follow later. Most people will choose to visit Maine, New Hampshire and Vermont during their New England fall road trip (and spoiler alert: this is also where I’ll be suggesting you go!), so this timeframe works very well for these areas.

The central part of Vermont will often peak right around Indigenous People’s weekend in October, and for a getaway to popular towns like Stowe and Woodstock, this is the perfect weekend to plan your trip.

Massachusetts often peaks right around Indigenous People’s weekend as well, with southern MA peaking a week or so later.

The greater Boston area, and Connecticut will peak mid-late October, depending on the year.

How Many Days Do You Need In New England In The Fall?

The great thing about New England in the fall is that you can easily do a weekend getaway and still pack a lot in, or you can plan an epic 12 day road trip for the ultimate adventure. And either way, it’s going to be incredibly memorable.

If you’re coming in from a distance, especially if you’re flying in, I would say 10 days is a great option, 12 days is even better, and 7 days is also wonderful. Of course, with 12 days, you’ll be able to see so much or plan extra time in some places. But even with 7 days, you’ll get to see quite a bit.

If you’re local to New England, and don’t have 10 days, 7 days is again a nice sweet spot. 5 days will also work in this case. And, as mentioned, even a weekend away will allow you to experience some of the best this region has to offer in the fall season.

The great thing about the best places for fall foliage are located in some of the smallest states, so you can cover a lot of ground in a short amount of time.

Best Places To See On A New England Fall Road Trip

While every New England state has something special to offer during fall foliage season, for the purpose of seeing the absolute best spots, I recommend sticking to Maine , Massachusetts , New Hampshire and Vermont . And flying into Boston.

Because these areas offer the most spectacular displays of foliage, most picturesque scenery, tons of things to do, and they’re all reasonable close to one another, allowing you to maximize your time.

Here’s why I don’t necessarily recommend states like Connecticut or Rhode Island if you have less than 10 days – they’re further away from the best places to see in the fall.

I truly love every single New England state, and I do really enjoy Connecticut in the fall. However, it’s so far west that you’ll spend more time driving to get there, and possibly forgoing some really spectacular places in Maine, New Hampshire, Massachusetts, and Vermont.

If you have 10 days or more for a New England fall road trip, then I would highly suggest you consider adding in the Litchfield Hills regions of Connecticut , which you’ll see I included in my itinerary. It’s also very close to The Berkshires region, so you can combine it with that part of the trip, depending on how much time you have. However, with less than 10 days, I personally don’t feel like it’s worth it. Especially for first-timers.

If you’ve already seen some of the places I’m recommending in this post, then definitely try to swing over to Connecticut and experience a new area during the fall!

If you have less than 10 days, you may even want to focus all your time on Vermont and New Hampshire. The reason for this is because some of the best places for fall foliage in Maine are further north. I think places like Acadia National Park are very worth seeing (and you’ll see I’ve incorporated it into some of my itineraries!). However, if you prefer a slower pace and less driving, Vermont and New Hampshire are the absolute best places to see .

Some Things To Know About My Itineraries

They all begin in Boston , assuming that’s where most people will fly into if visiting from a distance. If you fly into a different airport, or are driving in, you can easily adjust your plans as needed.

They’re done in true road trip style , meaning there’s a lot of driving, and mostly 1-night stays. There are some places I recommend 2 nights in, but you can adjust this based on your preferences. If you want to stay longer in one place, definitely go for it!

I give you options! Of course, I stand by all my suggestions ☺️ However, I know everyone has different travel styles and speeds, so I encourage you to to tailor this to what you think you’ll enjoy the most. I’ve given you suggestions on how to adjust the itinerary based on your preferences.

10 Day New England Fall Road Trip Itinerary From Boston

Okay, let’s get into my perfect New England fall road trip itinerary options! We’re beginning with my suggestions for an incredible 10 day adventure.

10 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Explore Boston Or Take A Day Trip To Salem Day 3-4 : Bar Harbor/Acadia National Park + An Optional Stop In Salem Day 5 : Jackson, NH Day 6 : Franconia, NH (Driving The Famous Kancamagus Highway To Get There!) Days 7-8 : Stowe & Woodstock, VT Day 9 : The Berkshires and/or Litchfield, CT Day 10 : Back To Boston + A Stop In Sturbridge, MA or Litchfield, CT

Breakdown Of The 10 Day Itinerary Option

Day 1: Arrival In Boston Take this time to arrive, get settled, and maybe take in a few sites around the city! Have some time on your first night here? Jump down to Day 2 for some suggestions on what to do!

Where To Stay In Boston:

• Luxury : The Langham
• Splurge : Boston Harbor Hotel
• Moderate : Revere Boston Common

Pro Tip On Fall Foliage In Boston : Foliage peaks later than the rest of the places listed in this itinerary – usually mid-late October. So while you probably won’t see peak foliage in Boston if you plan your trip for peak foliage in Vermont, New Hampshire and Maine, it may catch a glimpse of it on your back if you’re planning a longer trip! Or, you can leave the airport to immediately begin your drive to Maine, and plan to stay a night or two in Boston before you have to fly out.

Day 2: Explore Boston

Boston during the fall season has so much to see and do, but here are some highlights to consider if it’s your first visit:

• Public Gardens (very scenic garden area with a beautiful pond and pedestrian bridge (also makes for lovely photos!). This is a good spot for fall foliage in the city, too.
• Newbury Street for shopping
• The North End for history and food
• Beacon Hill for charming cobblestoned streets at the famous Acorn Street
• Take a food tour if it works with your schedule. There’s incredible food to be had in Boston, and taking a tour with a local expert is a great way to sample lots of delicious things in a short amount of time!

Click here to check out my post on the best Boston food tours!

Day 2: Optional Day Trip To Salem

If you would prefer to take a day trip to Salem, rather than stopping on your way to Acadia National Park, this is a great option! And really, there’s no right or wrong choice here – it just comes down to which you prefer.

Salem is an easy day trip from Boston without a car because of this convenient ferry! Click here to check out the Boston → Salem Ferry!

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 😉

Day 3: Drive To Bar Harbor & Acadia National Park

Acadia National Park is one of the best things to do in New England year-round, so this is definitely a must if you’ve never been. It also offers some really wonderful foliage, and fall is my personal favorite season to visit for this reason.

This drive from Boston to Bar Harbor takes about 5 hours without stops, which is why I usually suggest you make a pitstop to break up your journey. I actually have some posts on stops you can make along the drive, so be sure to check those out below.

But since Salem is really the ultimate fall destination in Massachusetts, I suggest you pick that as a stop on the drive 🙂

Bar Harbor is the town adjacent to Acadia National Park , and where most people will choose to stay when visiting. Once you arrive, take some time to get settled, and then head out into downtown Bar Harbor to explore this charming seaside town, visit the shops, and grab a great dinner!

Where To Stay In Bar Harbor:

• Bayview Hotel . An oceanfront boutique hotel with awesome views. Perfect for a splurge on your trip!
• Bar Harbor Villager Motel . Clean, updated and spacious. Also, walkable to everything in town.
• Little Fig Hotel . A cute, modern boutique hotel walkable to town.

Here are some posts that will help you further plan this portion of your trip:

• Best Stops To Make Driving Boston To Portland, Maine
• Best Stops To Make Driving Portland to Acadia National Park
• The Perfect Acadia National Park Itinerary (read this one for more information on Bar Harbor and things to do!)
• Best Time To Visit Acadia National Park
• Best Towns To Stay When Visiting Acadia National Park

Day 4: Explore Acadia National Park

Even in just 1 day, you can visit some of the best places in the park, and also some really wonderful fall foliage spots. Here how I suggest you plan your day:

If you’re up for it , starting your day with sunrise at the top of Cadillac Mountain is always incredible! It’s one of the first places in the U.S. to see the sunrise, depending on the time of year, and starting October 7 through March, it’s the very first spot in the country to see the sun come up. This will be great for fall foliage, too. You can also choose to do this the following morning before leaving.

Next, head to the Jesup Path scenic walk , which is especially beautiful in the fall season.

Then, park at the Sand Beach parking lot , and walk the Ocean Path for incredible views . This is 1-mile each way, but offers some of the most iconic views in the park, including the Otter Cliffs and Thunder Hole. It’s also flat and easy, making it very relaxing. Have your camera ready for this one!

For a more advanced hike with awesome foliage views, you can do the Beehive Trail from Sand Beach lot, too.

Continue on Park Loop Road to Jordan Pond House for lunch , and enjoy the views of the pond and mountains. You can also choose to walk around the pond if you have time after lunch.

For more foliage views, hike the Bubble Rock Trail after lunch.

Day 5: Drive To Jackson, NH + Spend The Night

Without stops, this drive takes about 4 hours and 15 minutes.

One stop I suggest making on the way if you enjoy local craft beer is the Oxbow Beer Garden in Oxford , ME . It’s got a very cool outdoor setting, and they have fantastic craft beer.

I recommend spending the night in Jackson because it’s a longer drive from Bar Harbor, and there are some fun things to do in the area. Also, there’s a very scenic drive called The Kancamagus Highway that’s stunning in the fall season with foliage, and I want to make sure you have time to drive it. But more on that in Day 6 🙂

Here are some fun fall things to check out in Jackson:

• The Cog : This mountain railroad takes you to the summit of Mount Washington, the tallest peak in New England! It’s about 45 minutes from Jackson, but you’ll drive through Crawford Notch State Park , which is very scenic, and The Cog is simply incredible in the fall season. If you leave Bar Harbor early enough and have time to do this, I highly recommend it!
• Honeymoon Covered Bridge & Flossie’s General Store
• Glen Ellis Falls
• The cute town of North Conway

Where To Stay In Jackson:

• Christmas Farm Inn (this place is super cozy!)
• The Inn At Thorn Hill & Spa

Option To Stay In North Conway : North Conway is only about 12-15 minutes from Jackson, so you can really stay in either. I think Jackson has better hotel options, and it’s a bit closer to The Cog, which is why I suggested you stay there. But either town works for your New England fall road trip!

Here are some fun things to check out in North Conway if you choose to visit:

• Cathedral Ledge Distillery
• Ledge Brewing Company (between North Conway and Jackson, technically)
• The cute downtown area and Zeb’s General Store (one of my all-time favorite general stores!)
• North Conway Scenic Railroad

Day 6 – Drive The Kancamagus Highway To Franconia, NH

The Kancamagus Highway (Route 112) is a scenic drive that’s regarded as one of the best drives for fall foliage, so this is something you’ll definitely want to do on your New England fall road trip. It connects the towns of Woodstock and Conway, so you can easily start this drive just a few minutes from Jackson or North Conway.

For this day, I suggest you get up early to make sure you have time to explore Franconia Notch State Park after driving The Kanc.

Tips For Driving The Kanc:

• Remember earlier in the post when I said you’ll lose cell service in much of New Hampshire and Vermont? Well, this is one of those drives where there’s no service, so offline your maps before starting!
• There are no bathrooms or gas stations on the drive, so plan accordingly.
• The Kanc takes about 45 minutes one-way without stops, but you’ll want to budget about 2 hours to make some stops at the overlooks.
• During the fall season, especially on weekends, it’s possible traffic could slow down as people try to pull in and out of the parking areas. Plan for some slower traffic.

Pro Tip : Before hopping onto The Kanc, there’s a great little place called Cheese Louise just before the entrance to The Kanc, and this is an awesome place to grab some food before the drive! Especially on a chilly, fall day, a grilled cheese sandwich totally hits the spot, right? 😍

Stops To Make On The Kanc (in order from Conway to Woodstock):

• Albany Covered Bridge
• Rocky Gorge Scenic Area (parking can be found at 44.0016667175862, -71.27716637107925)
• Sabbaday Falls
• Sugar Hill Scenic Overlook
• CL Graham Wangan Overlook
• Hancock Overlook (this one is right at the famous hairpin turn – can’t miss it!)
• Lincoln Woods Trailhead – Scenic suspension bridge over the river that’s not far from the parking lot.

🍁 Before hopping on The Kanc, consider downloading this great audio tour to enhance your drive – Click here to check out this audio tour!

There are also tons of hiking trails along The Kanc , so if you’re looking to squeeze in a hike on the drive, this is something to consider. But if you don’t have extra time, I would suggest moving on to Franconia Notch State Park, and only doing hikes along The Kanc if you’re able to add an extra day in.

After The Kanc, your next stop is Franconia Notch State Park . And this is where most of the top things to do are , especially in the fall season .

Flume Gorge is one thing I recommend you do if you can only pick one attraction. Flume Gorge is a very fun 2-mile loop trail that takes you over 2 covered bridges, and through the granite gorge. Along the trail, you’ll have some really gorgeous spots to admire the fall foliage, too.

Not sure if this is right for your itinerary? Click here to check out my detailed post in if Flume Gorge is worth visiting , and everything you need to know to plan the perfect visit.

Pro Tip: Buy your Flume Gorge ticket online in advance to save a few bucks! On weekends in the fall season, it’s also possible that certain time slots will sell out. This is another reason to book in advance.

If you have time to explore more of Franconia Notch State Park, I also recommend these activities:

• Cannon Mountain Aerial Tramway
• Artist Bluff Trail (famous spot that ends overlooking Echo Lake – amazing during foliage season!)
• The views at Echo Lake Beach

Where To Stay Near Franconia:

• Sugar Hill Inn – 15 mins from Franconia Notch Park, and is rated as the best B&B in New Hampshire!
• Riverwalk Resort – 5-7 mins from the top attractions in Franconia.
• Woodstock Inn & Brewery – Cozy inn with a brewery.

Here are some posts to help you plan this portion of your trip:

• Fun Things To Do In Franconia, NH
• Fun Things To Do In Littleton, NH
• Fun Things To Do In Lincoln, NH
• Where To Stay In New Hampshire In The Fall
• Where To Stay In The White Mountains: Guide To The Towns

Day 7 – Drive To Stowe Or Woodstock, VT

Begin your day in New Hampshire with a country breakfast at Polly’s Pancake Parlor! This place is famous in New England, and truly has some of the most amazing pancakes I’ve ever had. It does get busy in the fall season, but man, it’s so worth it.

Then, on to Vermont you go! For the next 2 nights, you’ll want to choose between Stowe and Woodstock, VT as your home base. These towns are the absolute best to visit in Vermont during a New England fall road trip because of foliage views and small-town charm. They’re only 1 hour and 15 minutes from each other, so, you can choose where you want to stay, and then visit the other as a day trip.

The drive to both Stowe and Woodstock is 1 hour and 30 minutes from Franconia , and since this is a shorter drive, you can make some stops along the way, or drive straight there. Stowe and Woodstock both have a lot to do, even though they’re small towns, so it’s beneficial to drive straight there and make sure you have plenty of time to explore.

If you choose to stay in Woodstock, I suggest stopping at the King Arthur Baking Company campus on your way because it’s pretty much on the direct route. It’s a really fun place with fresh baked goods and breads, a café, and a fun shop where you can stock up on pantry staples and baking mixes.

Do I recommend you stay in Stowe or Woodstock? I honestly love both equally! There’s no wrong choice here.

The biggest difference between the two is that Woodstock feels a bit more upscale, and Stowe definitely has a very casual feel to it. But the difference is minor. Both have charming covered bridges, great shops, amazing restaurants, a quaint town feel, and plenty of things to do.

Where To Stay In Stowe :

• The Green Mountain Inn . It’s located right on Main Street, so you can walk to a lot of places.
• Spruce Peak Resort . Perfect for those wanting a resort feel, and it’s right off the scenic Smugglers Notch drive. There are rooms with gorgeous mountain views here, too.

Where To Stay In Woodstock :

• The Woodstock Inn & Resort . It’s referred to as Vermont’s most beautiful address, and it’s in the heart of Woodstock’s village. This is a luxury hotel that’s worth it!
• 506 Inn On The River . Located just outside of the village, this is a modern and cozy inn, well … right on the river 😉

Here are some posts that will help you plan your time in Stowe and Woodstock:

• Best Things To Do In Stowe
• Best Things To Do In Woodstock

Day 8 – Explore Stowe & Woodstock, VT

Depending on where you stay, you’ll want to take a day trip to the other town this day. Below are breakdowns of the can’t miss things to do in each town .

Best Things To Do In Stowe :

• Explore the cute shops along Main Street (don’t skip the Stowe Mercantile!)
• Drive Smugglers Notch for amazing foliage.
• Ride the gondola to the top of Mount Mansfield, the highest peak in Vermont (this is epic during the fall season!). This is located at the midway point along the Smugglers Notch drive.
• Visit Emily’s Covered Bridge, and learn about it’s spooky history.
• Sample the hard cider at Stowe Cider.
• Sip on craft brews at Alchemist Brewing (one of my favorites in New England).

Best Things To Do In Woodstock:

• Stroll through the charming downtown shops and eateries.
• Pop into Mon Vert Café for a warm drink.
• Snap a photo with Middle Covered Bridge in town.
• Drive over Taftsville Covered Bridge to visit Sugarbush Farms. You’ll be able to sample homemade cheese and fresh maple syrup here, and also take in amazing foliage views.
• Visit Billings Farm & Museum.
• Drive over to Sleepy Hollow Farm to see the famous farm landscape spot.

Day 9 – Drive To The Berkshires Or Litchfield, CT

Next up – The Berkshires or Connecticut! This choice is yours entirely. Let’s start with the option to drive to The Berkshires.

The Berkshires is an iconic region in Massachusetts that’s a really great one to visit for fall foliage. Here, you’ll find cute towns, loads of fall color, lots of scenic hikes and walks, and awesome dining options.

Depending on which town in Vermont you’re coming from, the northern region of The Berkshires area will be just over 2 hours from Woodstock, or just over 3 hours from Stowe .

The drive from either town to The Berkshires will pass through Rockingham, VT, and you’ll definitely want to stop here to visit the Vermont Country Store! There’s also the very cute Kissing Covered Bridge here that makes for a fun photo.

Once you arrive in The Berkshires, I suggest you start in Williamstown, and drive the scenic Route 7 down to Sheffield. This drive without stops takes about 1 hour and 15 minutes, but I would budget at least a few hours to make stops and enjoy some other fun activities. This route packs a lot into a perfect fall day, without a lot of driving.

During this drive, these are the best stops to make:

• The Mount Greylock Auto Road to the highest peak in Massachusetts (absolutely amazing in the fall season!).
• Make a detour off Route 7 to Bartlett’s Orchard in Richmond for the perfect fall farm experience.
• Continue with your short detour to Hilltop Orchards, which is 5 minutes from Bartlett’s, and where you can sip on artisanal craft ciders!
• Walk through the charming town of Lenox.
• Stroll through quaint Stockbridge, too!
• Snap photos with the covered bridge in Sheffield.

Where To Stay In The Berkshires:

• The Red Lion Inn . A historic and famous inn in the heart of Stockbridge.
• The Dewey . A cozy, traditional New England B&B in Lenox.

The other option is to drive to Litchfield, CT , which is south of The Berkshires. It’s a longer drive from Vermont, but you could also turn this into a fun road trip day by driving the same Route 7 itinerary as mentioned above through The Berkshires, and then continue on to the Litchfield Hills. I would probably only choose this option if you wanted to take your time exploring the awesome stops along Route 7 in The Berkshires, arrive in CT in the evening, and then explore this region of CT the next morning before your drive back to Boston.

How To Spend Your Time In Litchfield Hill, CT:

Since you’re likely coming down through the western border of Massachusetts, I would start in Kent, and work your way east. You probably won’t have time to do everything on this list, but pick and choose based on your preferences and schedule.

• Explore the cute town of Kent, and then visit Kent Falls State Park if you have time.
• Continue to follow Route 7 to New Milford. The drive is very scenic!
• Stop in New Milford to enjoy the quaint town, and then visit Lover’s Leap Bridge.
• Head over to Washington, and then continue on to Mount Tom State Park for awesome foliage.
• End in the charming town of Litchfield.

Where To Stay In The Litchfield Hills : Litchfield Inn . Refined and still very cozy, and one of the best in the area!

Should I do The Berkshires or Litchfield, CT? Personally, I would stay stick to The Berkshires since this will allow you a more relaxed itinerary. There’s so much to do, and plenty of foliage scenery to take in. If you do the Route 7 drive quicker than you were anticipating, you could always shoot down to the Litchfield Hills for an impromptu adventure 🙂

I would choose to add on the Litchfield Hills if you’re feeling adventurous, and really want to see as much of New England as possible.

Day 10 – Drive Back To Boston, Stopping In Sturbridge or Litchfield On The Way

If you have time to explore another cute town on your drive back to Boston, I would suggest either tacking on a quick drive through the Litchfield Hills, CT if you didn’t already, or a stop in Sturbridge, MA. Sturbridge is more on the way to Boston, and offers beautiful foliage.

How to spend your time in Sturbridge, MA :

• Visit Old Sturbridge Village for all the cozy fall New England vibes (this is a must if you have time!).
• Pop into Saw Dust Coffee & Dessert Bar for lunch and treats.
• Sip on craft beer at Altruist Brewing Company.

And of course, as mentioned in the previous day’s itinerary, the Litchfield Hills region has plenty to offer for foliage views, small towns, and beautiful scenery.

But, if you have a flight to catch, then don’t risk it, and head straight to the airport! 🙂

Optional Adjustments For The 10 Day Itinerary:

• You can easily cut out Acadia National Park, and head straight to New Hampshire, and choose to spend more time there. Acadia is out of the way, and further north, so I know it doesn’t suit everyone’s plans. This would allow you time to definitely ride The Cog, and have a more relaxed schedule.
• If you would rather have more time in Vermont, you can skip The Berkshires/CT. This is personal preference! Both areas are amazing for fall foliage, but nothing is quite like Vermont in the fall. This would allow you time to move at a slower pace. If you decide to skip The Berkshires/CT and stay in Vermont for a third night, see my 12 day itinerary, option 3 for suggestions on what to do!

12 Day Road Trip Itinerary Option

If you have 12 days (or more!), this is truly awesome. I would follow my 10 day itinerary, and then take one of these suggestions:

Option 1 : Add in 1 day to see Litchfield, CT after The Berkshires . Since you have the extra time, you can definitely see the Litchfield Hills region of Connecticut with this itinerary! I would recommend this option for those who really want to see as much of New England as possible, and make all the rounds.

Option 2 : Add an extra day to Littleton/Franconia. This region has so many great hikes and places to spot fall foliage. It’s well worth adding a day to this part of the trip if you have the extra time. This would allow you a half day to ride The Cog, and takes more scenic walks and hikes to enjoy the fall foliage.

Option 3 : Add an extra day to Vermont. On your extra day, you can take a day trip to Burlington and Shelburne, or spend the day driving the back roads .

Burlington & Shelburne, Vermont things to check out :

• First, the drive from both Stowe and Woodstock to Burlington on I-89 is beautiful in the fall. You’ll see lots of mountains ablaze with fall color.
• In Burlington, check out the waterfront area, and walk along Lake Champlain.
• Burlington also has an awesome craft brewery scene, and Foam Brewers is especially great.
• The American Flatbread restaurant in Burlington is a cozy place to stop for lunch.
• Church Street Marketplace in Burlington is a must!
• In Shelburne, you’ll want to spend most of your time walking around Shelburne Farms. This is a historic farm once owned by the Vanderbilt family, and has beautiful hiking trails, and you can also sample their homemade cheeses. Definitely do the Farm Trail, which takes you to an epic view of Lake Champlain.

Vermont back roads driving itinerary near Stowe :

This drive is easier to do from Stowe, but it’s also doable from Woodstock if you’re okay with a longer day. This itinerary is is order based on departing from Stowe, but you can also adjust based on which town you’re coming from 🙂

• The covered bridges in Montgomery, including Montgomery covered bridge (which is actually in Waterville), and Longley Covered Bridge.
• Barn Owl Bistro is a hidden gem nearby that’s a great little pitstop.
• The town of Cabot and the nearby AM Foster Covered Bridge are really beautiful areas to visit full of rustic Vermont charm.
• Peacham is a very small town with iconic landscapes and scenery.
• Bogie Farm in East Ryegate is a landscape that worthy of a postcard, and is especially beautiful in the fall.
• The drive between all these destinations will also be lovely and scenic, and packed with fall color.

1 Week (7 Day) New England Fall Road Trip Itinerary

If you have 7 days, welcome to your itinerary! This option is the same as the 10 day option, but eliminates Acadia National Park to save time.

7 Day Road Trip Overview

Day 1 : Arrival In Boston Day 2 : Drive To Jackson, NH + A Stop In Salem, MA Day 3 : Drive To Franconia Along The Kancamagus Highway Days 4-5 : Drive To Stowe or Woodstock, VT + Stay 2 Nights Day 6 : The Berkshires Day 7 : Return To Boston

For this itinerary, you can also eliminate The Berkshires, and stay an extra night in Jackson or Franconia.

5 Day New England Fall Road Trip Itinerary

With 5 days, you can go in a few different directions, and below, I break down my suggested options, and the benefits of each. This way, you can tailor it to your preferences.

Option 1 : Spend two nights in Boston with a day trip to Salem, then spend 3 nights in Stowe/Woodstock, VT.

Option 1 is perfect if you prefer staying in one place longer. This itinerary will allow you to stay in the same hotel in Boston for 2 nights, and take an easy day trip to Salem for the perfect fall day of Halloween fun and history! Then you can pick up your rental car (if you haven’t already), and drive to Stowe or Woodstock, VT for 3 days to explore both towns.

With 3 days in Vermont, you can easily see both Stowe and Woodstock, and maybe even plan a day of driving around the back roads. See the 12-day itinerary option for my suggestions on driving the back roads around Vermont during foliage season .

Option 2 : Spend 1 night in Boston, stop in Salem on your way to Franconia and spend 2 nights in Franconia. Then spend 2 nights in Stowe/Woodstock, VT, and then drive back to Boston.

Option 2 is perfect for those who still want to see as much as possible in 5 days. You’ll get to see a bit of New Hampshire and Vermont, while making a stop in Salem.

Note: For this itinerary, I would drive from Salem to Conway, and the drive The Kancamagus Highway on your way to Franconia so you get to experience the fall foliage along this route. But this itinerary option eliminates the stay in Jackson, as there are more fall things to do in Franconia.

Option 3 : Spend 1 night in Boston, 1 night in Salem, 3 nights in Stowe/Woodstock, VT, and then back to Boston.

Option 3 is perfect for those who really want to spend some time in Salem. This itinerary allows you to spend a whole night in Salem to really enjoy all the Halloween festivities and tours, and then you can spend 3 beautiful days in Vermont.

I excluded New Hampshire from this option because I felt like it would be too much to cram in when adding 1 night in Salem. But if you were feeling adventurous (I’ve been there, I get it! 😂), you can drive to Franconia, NH for 1 night after Salem, and then do 2 nights in Vermont instead of 3.

3 Day New England Fall Road Trip Itinerary

3 days in New England is the perfect long weekend getaway!

With 3 days, I suggest you stay in one location , and add day trips . If you’re flying into Boston, you can stay 1 night in Boston if needed, and then drive to Vermont or New Hampshire for 2 nights. If you’re not flying in, you can spend all 3 nights in Vermont or New Hampshire.

Stowe is very close to New Hampshire, and it’s only about 1.5 hours from Franconia. You can easily do a day trip from Stowe to New Hampshire, or vice versa, for this type of itinerary.

It would also be easy to work in a stop in Salem, MA, either on your way in or out of Boston.

Weekend New England Fall Road Trip Itinerary

For a weekend getaway in New England (essentially, 2 days), I would also recommend you stay in one place and take a day trip. For this itinerary, I almost always suggest Stowe or Woodstock. You can stay in either town, and spend 1 day exploring that town, and then the next day, exploring the other as a day trip.

Vermont Fall Road Trip Itinerary

Looking to just see Vermont? Excellent choice. It’s my personal favorite fall destination in New England (even though it’s a very close call 😉)

For a Vermont fall road trip , you can really do it in anywhere from 5-7 days. Of course, more is better to really see everything, but generally speaking, you can actually make it happen in a week or less. A popular route to take in Vermont is Route 100 , which runs the entire length of state, right through the middle. This allows you opportunities to veer off and see some other places as well.

For the purpose of this itinerary, I’m going to provide a week-long (7 day) itinerary, and you can adjust it to your own plans.

Day 1 : Bennington & Manchester Day 2 : Drive to Woodstock, stopping in Grafton and Weston on the way Day 3 : Spend the day in Woodstock Day 4 : Drive to Stowe, stopping in Montpelier if you’d like Day 5 : Spend the day in Stowe Day 6 : Staying in Stowe, take a day trip to Burlington & Shelburne Day 7 : Drive back

Day 1 Suggestions : Bennington and Manchester are pretty close to each other, so you can easily do both in one afternoon. There are some wonderful covered bridges in the area to see, and here are some more things to check out:

• The Bennington Battle Monument for fall foliage scenery.
• Downtown Bennington for shopping on Main Street (small, but cute!).
• Apple Barn is a few minutes from Main Street for a fun country store and bakery.
• Zoe’s in Manchester for lunch (great sandwiches!)
• Downtown Manchester for shopping in a cute town (don’t skip Northshire!)

Day 2 Suggestions : Grafton is a very small town, but it’s quintessential Vermont. It has a cute little cheese shop, and a nice little market/cafe called MKT Grafton, which is perfect for a quick bite. Also, swing by Weston to visit the Vermont Country Store.

For the rest of the itinerary, refer to the 10 day option for details 🙂

Click here to check out my post on a Vermont covered bridges road trip!

New Hampshire Fall Road Trip Itinerary

My second favorite fall foliage destination! Here’s my suggested itinerary for a New Hampshire-only fall road trip.

To just see New Hampshire , you can also spend anywhere from 4-7 days.

With 4 days, you can easily just stick to the White Mountains region, but I’m here to give you all my tips on even more awesome places to see in the fall season in New Hampshire ☺️ So, this itinerary will be 7 full days , but adjust as you need to!

Day 1 : Portsmouth Day 2 : Lake Winnipesaukee Days 3-4 : Littleton/Franconia Days 5-6 : North Conway/Jackson Day 7 : Drive back

Connecticut Fall Road Trip Itinerary Option

If you’ve seen all the “hot spots” around Vermont, New Hampshire, Massachusetts, and Maine, and you’re looking to explore a new part of New England in the fall, Connecticut should be next on your list!

As mentioned, my favorite place in Connecticut for fall foliage is the Litchfield Hills region. I always like to share that this region was what inspired Amy Sherman-Palladino’s creation of Stars Hollow, so Gilmore Girls fans will especially love this area.

The Litchfield Hills is very compact, and you can easily do a lot in a weekend here. However, 3-4 nights will allow you a nice, leisurely pace to explore all the amazing things this region has to offer in the fall.

The best towns to stay in in the Litchfield Hills region are:

• New Milford
• Washington/Washington Depot

Of all these towns, Litchfield probably has the most options when it comes to shopping and dining, however, they’re all very quaint and charming. I would pick whichever one has the best hotel for your plans.

If you have extra time for your Connecticut fall road trip, you can tack on places like Canaan to the north of the Litchfield Hills region, drive to Glastonbury, and then through the River Valley region, which includes the adorable towns of Chester and Essex. You can also choose to end your road trip in Mystic.

What To Pack For A New England Fall Road Trip

I always start every New England packing guide with the same thing, and this post is no different: begin to check the weather reports 5 days out from your trip to get an idea of what the weather will be like . And keep checking it until the day before you leave .

This is because weather in New England can change quickly, especially in the fall season. It’s not quite as dramatic as say … Iceland 😉 But, it can change and vary a bit. Generally speaking, fall will be chilly and a bit rainy. However, you could also have warm and sunny days. For longer trips, you’ll want to pack for both scenarios.

Here are some things I recommend you consider when packing for a fall road trip through New England:

Waterproof hiking boots . If you plan to do any hiking, or even nature walks, you’ll want a pair of sturdy boots that are waterproof. Even some attractions like Flume Gorge and other waterfalls in New Hampshire are pretty wet, so this is a good idea to stay dry and comfortable. I really like the Eddie Bauer K-6 Hiking boots. Find the women’s version here and the men’s version here . They’re a much less expensive version of the famous Danner hiking boots featured in the movie Wild !

Good hiking socks to keep your feet dry . An awesome brand to support is Tarn Tough Socks , which is a Vermont-based company. They’re an investment, but they’re also the best, and come with a lifetime guarantee!

Waterproof rain jacket to stay dry if it rains . You won’t want to let the rain slow you down, especially if there’s a lot in the forecast! So definitely pack one that’s completely water proof ( not water-resistant).

Layers . The best way to dress in the fall season is with layers. Under your rain gear, flannels, sweaters, and lightweight t-shirts (both short-sleeved or long-sleeved) work great.

Jeans . These work really well for most days. Fall in New England is pretty casual.

Hiking clothing . For any hikes you want to do, pack whatever clothes you typically wear and feel comfortable in 🙂

Comfortable sneakers or boots . When it’s not raining, a good pair of comfortable sneakers or cute boots work perfectly, depending on your plans. Since I drive from New York, I don’t usually have to worry too much about weight limits on a suitcase, so I’ll throw a pair of sneakers, flat boots/booties, and my hiking boots into the car. This is usually all I ever need.

Dinner outfits . New England is home to incredible places for farm-to-table dining, some of which are a bit more fancy. If you plan to go out for a nice dinner or two, you’ll want to pack accordingly. New England isn’t super fancy, so women can do a casual dress/jeans and a nice top with booties in the fall, and men can easily do dark-wash jeans and a button down top.

Reusable water bottle . You’ll need to stay hydrated while out exploring!

Day pack . If you plan to do any hiking, you’ll want to bring a day pack with you to carry your essentials. If you don’t plan to do any hikes, you can probably skip this, as you can keep most everything you need in your car or room.

Does It Snow In New England In The Fall?

Here’s the thing – it might if you’re up in the mountains. However, it doesn’t usually snow during peak foliage times. Usually, New England gets its first snow of the year later in October or early November. So, I wouldn’t worry about packing any snow gear or winter boots for your fall road trip.

How Do To A New England Fall Trip On A Budget

So, first thing’s first, you’ll unfortunately have to rethink what “budget” means in New England, especially during peak season in the fall. It’s generally more expensive than other areas of the country regardless of the reason, so during prime foliage times, prices will go up significantly.

Especially in the past, I never had the money to spend on several nights at hotels during this time of the year, so I have learned to do it on more of a budget. Not necessarily cheap, but not as tough on the wallet 😉 Here are my tips:

• Stay in motels. I love a good hotel splurge, and do it more now than I did in my 20s and early 30s. But for most of my road trips when the focus in exploring outdoors, I stay in motels with efficiency kitchens . You can find some really nice ones, and while they’re likely to be outdated, they’re usually clean and cozy.
• Efficiency kitchens allow you to make some meals at home. For a road trip style trip, this may be more challenging, as it’s hard to bring perishable items with you to store in a fridge. But I usually try to make my own breakfasts to save money, and pack snacks to have for lunch.
• Stay outside of town. If you’re really on a tight budget, you can stay outside of the towns you’re visiting. Places like Franconia, Stowe, and Woodstock charge premium rates for peak season, so you’re likely to find deals a town or two away.
• Go camping! If you’re really adventurous, you can go camping! There are camp sites all over New England, and this will definitely be more affordable. One thing to keep in mind is the colder weather, and for this reason, some camp sites may close down after Indigenous People’s weekend in October. But many remain open, and offer Yurt-style camping, too.

Is Fall In New England Worth It?

A resounding yes! I truly believe this is such a magical time to visit – if not the most magical time. Despite the crowds and the cost, it’s more than worth it. Many of the landscapes you’ll see are actual stock photos and postcards, and since so many people equate the fall season to all things cozy, there’s really no cozier place to be than in New England during foliage season.

More posts you may enjoy:

• Fall In New England: The Best Things To See & Do
• Vermont In The Fall: Festive Things To Do!
• Fall In New Hampshire: The Best Things To Do
• Fall In Massachusetts Ultimate Guide: All The Best Things To Do & Foliage Spots!
• The Best 7 Day New England Road Trip Itinerary For Any Season
• Best Stops To Make On A Boston To Stowe, VT Road Trip
• Vermont vs. New Hampshire In The Fall
• Maine In October: Best Towns For Foliage & Things To Do!
• Best Vermont Pumpkin Patches & Farm Stands To Visit In The Fall
• Awesome Corn Mazes In Vermont
• Best Time To Visit New England
• Best Time To Visit Vermont

That’s A Wrap On The Best New England Fall Road Trip Itinerary

And there you have it! All my tips and expert advice on planning the most epic New England fall road trip during foliage season! This truly is such a wonderful, once-in-a-lifetime experience that everyone should do at least once, and hopefully, you’re now well on your way to planning your own foliage adventure through New England!

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Experience Peak New England Charm in This Coastal Massachusetts Town

Welcome to Two Days Away , our series featuring weekend-long itineraries within a five-hour drive of your city—because sometimes we all just need a little adventure fix. Boston is considered the heart and soul of Massachusetts to many visitors, but the Bay State is brimming with seaside towns that are often unjustly overlooked. Only an hour North of Boston, Rockport is a prime example, full of storybook houses, sandy beaches, and winding streets—it’s as New England as you can get.

At the tip of the Cape Ann Peninsula, Rockport is surrounded by the Atlantic Ocean on almost all sides, making it a seafood-lovers paradise. It’s definitely worth a visit year round, but spring and summer is when Rockport truly comes alive. With small fishing vessels circling, seagulls roaming the skies, kayaks along the shore, and the air full of the smell of freshly caught lobster, it’s the perfect spot for those looking for a little rest and relaxation while delving into the excellent food scene and outdoor activities.

One or two coffee shops, artist hideouts, antiques, quaint restaurants, and a few bars—it’s almost reminiscent of Stars Hollow ( for those in the know ). “We often describe Rockport as Rockwellian,” explains Marshall Tulley, owner of Addison Choate Hotel. “It has a classic American small-town vibe that is very special. All of the shopkeepers and artists will welcome you into their stores and galleries and tell you their story. The historic buildings give the town a feeling like it is frozen in time.”

Here’s how to make the most of your trip.

Travel time:

10 minutes from Gloucester

If you don’t do anything else: Browse the local art galleries and stroll along historic Bearskin Neck

If you’re a fan of local  artwork, you’re in for a treat. Home to over 30 galleries with works of art depicted by over 400 artists in the area (many of which are on Bearskin Neck and Main Street), Rockport’s art scene is just as ‘small-town vibey’ as the town itself—every artist seems to know one another. Incredibly friendly, artists will beckon you in to explore their creations and tell you their story. Most of the artwork in the area draws inspiration from Rockport’s surroundings—but no two are ever the same. That’s the fun thing about the art scene here. You can wander up and down the streets as many times as you want, and still find a piece you haven’t seen.

Fill your days:

Beaches near rockport.

Though not as popular as its neighbors, Back Beach is a short walk away and is a quarter-mile stretch of shore that often disappears during high-tide. Though a little rockier than most, Back Beach is actually home to one of the most popular dive sites in Massachusetts. Speaking of diving fun—Old Garden Beach is another popular training site, so it can get quite busy on weekends. Close to the town, it’s not necessarily the best sunbathing beach, but it’s definitely worth the visit.

Outdoor activities near Rockport

Surrounded by the ocean in almost all directions, Rockport actually has some of the best outdoor activities and hikes. The infamous Halibut Point State Park is a unique coastal seascape with sprawling views as far as Crane Beach. The drive from Rockport town is a mere eight minutes, while walking will take a little over an hour. Though both viable options, one of the best ways to see Rockport and its surrounding landscapes is definitely by bike.

As mentioned above, Back Beach is one of the best dive spots around. Juvenile flounders, lobsters, and squid. Rockport doesn’t earn the reputation of some of the best seafood in Massachusetts for nothing. If being underwater isn’t your thing, then on top of it may be better. Believe it or not, MA is home to many species of whales (and sometimes sharks)—so a whale watch is a good bet. Depending on the season, if you leave from Rockport you’re likely to see Humpbacks, Finbacks, and Minke Whales.

“One of our favorite adventures is going out on the Rockport SeaVenture Lobster Boats pulling traps, visiting the seals, and learning about the history of the town and islands. There are two islands with lighthouses just off the coast, Thacher Island and Straitsmouth Island. You can take shuttles or kayak out to them, tour the grounds, and even visit the lighthouses,” says Addison Choate owner, Marshall Tulley.

Eat, drink, and sleep:

Restaurants & bars in rockport.

Head on over to Feather and Wedge at night. Not only will you find good cocktails and delicious bites, there’s a wrap-around bar that makes it surprisingly easy to chat to the locals and fellow travelers. Bean & Leaf Cafe is incredibly cute for grabbing a coffee by the sea, and the Ice Cream Store serves as a treat for a midday snack. Yummy year-round, Helmut’s Strudel hits a little differently during the cooler months.

Where to stay in Rockport

Hospitality and coziness can be found at family-owned boutique hotel, Addison Choate . Limited rooms on site make for a truly intimate stay. Owners Marshall and Courtney Tulley have done a superb job renovating the central property and making it a welcoming place for all. The warmth of the hotel is noticeable upon arrival, with a wrapping veranda laden with hanging flowers. Inside you’ll wonder if you’ve stepped into someone's home or a hotel.

No two rooms are alike. Pops of color, communal spaces, and quirky finishings—there’s a small nook for everyone. You’ll find a maze of rooms on the first floor filled with art, trinkets, and all the furnishings expected in a family home. Breakfast is also delivered in the morning.

With sprawling Ocean views and nautical-inspired rooms, The Cove at Rockport is another option if you want to be directly along Front Beach. Rockport Inn and Suites and Seafarer Inn are also near town. Rockport Inn is a short walk from the center, with ample outdoor space and an indoor pool perfect for families. Seafarer is slightly off-the-beaten-path, near Gully Point Cove and Gap Cove. Want more Thrillist? Follow us on  Instagram ,  TikTok ,  Twitter ,  Facebook ,  Pinterest , and  YouTube .

Hayley Domin is a Thrillist contributor.

Boston's duck boats are famous: What's their history?

What do you think of when you think of sports championship parades in Boston , besides the teams themselves?

That's easy - duck boats.

Those are the cool looking boat-like vehicles that can travel on land and water, and have become a staple in transporting athletes during championship parades. The New England Patriots , Boston Celtics, Boston Red Sox and Boston Bruins have all used the boats at such parades.

On Friday, they'll roll out for a nother parade celebrating the Celtic's newest championship.

But when the duck boats are not transporting championship teams through the streets, they can be seen traveling the streets and water of Boston showcasing the city to tourists and residents alike.

Live Coverage of the Celtics Parade: The duck boats are ready to rally! Follow the Celtics parade today

Cue the duck boats! Celtics 2024 NBA championship parade details

What are duck boats?

Duck boats are colorful, bulky, boat-like vehicles that travel throughout Boston on land and on water. Boston Duck Tours are 80-minutes in length - 60 minutes on land and 20 minutes on the Charles River. Boston Duck Tours began rolling through the streets of Boston in October 1994.

How many duck boats does Boston have?

There are 28 amphibious duck boats - called ducks - used by Boston Duck Tours. Each duck is colorfully painted and named after Boston landmarks such as "Fenway Fanny," "Kenmore Karla," "Charlie River," "Longfellow Bridget," "Miss Emma Science," "Beantown Betty," 'Beacon Hilda," and "Symphony Hal."

Do Boston duck tours go in the water?

Yes. Boston Duck Tours splash into the Charles River for approximately 20 minutes of each 80 minute city tour. According to the tour website, you will not get wet on the tour, but could get a light spray depending on the wind direction.

How many championship parades have used the duck boats?

The duck boats have been used for championship parades in Boston since 2002. The Boston Duck Boat website states, "Boston Duck Tours, over the years, has had the honor and pleasure of hosting four of Boston’s sports teams in Rolling Rally Championship parades 12 different times."

According to the website, with duck boats "players could stand on, and wave to the crowds below. It was close enough to get these players right up to their fans. But, also far enough to keep them from being mobbed by the crowds."

A brief history of duck boats

The History Channel explained that allied troops used duck boats to get artillery, supplies and soldiers ashore during  World War II .

" DUKW boats made their first appearance in combat during the 1943  invasion of Sicily  known as Operation Husky," History.com states. "The name 'DUKW' corresponded to General Motors’ manufacturing code (“D” is “1942 model,” “U” is “amphibious,” “K” is “all-wheel drive,” and “W” is “dual rear wheels”). Soldiers simplified this by calling them “ducks.”

"Like actual ducks, these boat-trucks with wheels looked a little awkward. But their weird design is what allowed troops to drive the vehicles from water onto land—a crucially important task."

Where do the duck boats depart from in Boston?

According to the Boston Duck Tour website , there are three departure locations:

• Prudential Center, 53 Huntington Ave.
• Museum of Science, One Science Park.
• New England Aquarium, Central Wharf.

How many duck boat tour companies are there in Boston?

Boston Duck Tours is the only duck tour company in Boston.

Do other cities have duck boats?

There are other states that do duck boat tours , like Tennessee, Alaska, Wisconsin, California, Florida, Maine and Texas, among others.

Protect Your Trip »

6 Top Boston Harbor Cruises

Venture on the water to explore Beantown's waterfront, maritime history and more.

Courtesy of City Cruises by Hornblower

Boston is the most populous city in New England – and for good reason. This Massachusetts metropolis may host modern shopping, dining and cultural attractions , but Boston is built upon a rich American tapestry created over the centuries that's still visible in its quaint neighborhood streets and stone houses. The city's historic harbor along the Massachusetts Bay set the scene for a significant portion of Boston's story; once the site of Revolution-era protests like the Boston Tea Party, this body of water is now primarily used for revelry. No visit to Massachusetts' capital city would be complete without some time on Boston Harbor.

If you'll be in Beantown during the warmer months, consider boarding a schooner for an hour or two of sightseeing. Cruises on the harbor offer a range of historical tours, romantic dinners, unique brunches with friends or even the chance to spot some endangered whales. Whether you opt for a tall ship or a smaller vessel, soak in city views and enjoy your time on the water with the following top Boston Harbor cruises.

Boston Harbor City Cruises by Hornblower – Boston Harbor Whale Watch Cruise

Price: Adults from $70; kids from $50 Duration: 3-4 hours

Hornblower's City Experiences brand offers a wide variety of land-based and on-the-water tours. One of the most popular options is its whale watching cruise, which it operates with the New England Aquarium . From Boston's Central Wharf, you'll head to Stellwagen Bank National Marine Sanctuary, one of the world's most active marine sanctuaries. Whales in the region include humpbacks, minke whales, the endangered right whales and more. You can also try to spot sea birds, dolphins and other marine life. Travelers say the boat tour is great fun and most report seeing whales on the trip.

Tours generally run daily from spring through fall. Exact departure times vary by season. You'll want to arrive at least 15 minutes early and take some medication if you're prone to motion sickness. If you plan to pair this cruise with a trip to the aquarium, you can book a combo ticket to save a bit of money. Boston Harbor City Cruises also runs a variety of dinner cruises.

Check prices & availability on:

Liberty Fleet of Tall Ships – Boston Harbor Day Sail

Price: Adults from $55; kids from $35

Duration: 90 minutes

Board a schooner from the Liberty Fleet of Tall Ships and sail Boston's historic harbor in fitting style. Your tour begins by embarking on the Liberty Star, which boasts a 76-foot mast. The crew is happy to answer questions about Boston during the sail, but know that there is no narration during the tour. Travelers delight in both the tour and the boat, noting excellent views.

The fleet sails Boston Harbor from summer through early fall. Sails typically depart several times each day in the afternoon; however, specific times may vary depending on the day of the week. You can also hop onboard for a brunch cruise, a fireworks cruise or for the yearly USS Constitution turnaround sail.

Classic Harbor Line Boston – Northern Lights Sunset Cruise

Courtesy of Classic Harbor Line Boston

Price: From $45 Duration: 2 hours

Along this evening tour, you'll be treated to skyline views as the sun dips below the horizon. During the journey, you'll also learn a little about Boston's history and its best sites such as Fort Independence, the USS Constitution , Old North Church's steeple and more. Refreshments are available for purchase onboard. Travelers approve of the cruise – especially the gorgeous ship – and its staff.

Departure times and days vary depending on both the sunset and the season. Keep in mind that ticket fees will be slightly higher in the high season. The company also hosts a number of themed and food cruises, such as holiday cruises and a trip that focuses on beer and barbecue.

Boston Duck Tours

Price: Adults from $52.99; kids from $37.99

Duration: 80 minutes

It's nearly impossible to visit Boston and not run into one of its renowned Duck Tours. This type of amphibious automobile was originally created as a military vehicle for World War II. The vehicles used today by Boston Duck Tours are uniquely designed to roll past city sights like Boston Common , the Old North Church and the Fanueil Hall Marketplace before or after launching into the Charles River for views of the Cambridge and Boston skylines. Past customers remember these unique tours as one of the best parts of their visit – and as a special draw for kids, the tour guides may allow children to briefly steer the boat in the water for a particularly memorable experience.

Trips depart from the New England Aquarium, Museum of Science and the Prudential Center; tour prices are the same regardless of departure point. Tours run in the warmer months, usually from late spring to fall. It's a good idea to book online in advance to secure your preferred tour time.

Massachusetts Bay Lines – Boston Harbor Moonlight Cruises

Courtesy of Massachusetts Bay Lines

Price: Adults from $28; kids from $15 Duration: 90 minutes

Referred to locally as Mass Bay Lines, this company runs an after dark cruise that travelers say has excellent views of the city lit up. If you're in need of refreshment, you'll find drinks (including alcohol) and snack onboard for purchase. For an extra special evening, sign up for a Full Moon Cruise, which takes place once per month from May to October.

Tours run a few times a month and generally start at 9 p.m. The company also runs daytime harbor cruises and themed cruises that welcome dogs onboard.

Charles Riverboat Company – Charles River Sightseeing Tours

Price: Adults from $27; kids from $18 Duration: 70 minutes

After cruising through the harbor, why not explore another Boston waterway? Along the historic sightseeing cruise of the Charles River, you'll see some of Cambridge's best sights like Harvard University and MIT , as well as Boston University, and the Back Bay neighborhood. The crew will offer tidbits and trivia during the tour. Tourgoers enjoy the outing and several mention that the company is great if booking a private charter for a large party.

Tours run late May though the end of September at 12:30, 2 and 3:30 p.m. If you wish to explore the Boston Harbor and the Charles River in the same trip, consider signing up for the company's Architecture Tour.

You might also be interested in:

• The Best Boston Tours
• The Best Hotels in Boston
• The Best Whale Watching in Cape Cod
• The Best Weekend Getaways in New England

Tags: Travel , New England Vacations , US Vacations , Cruises

World's Best Places To Visit

• # 1 South Island, New Zealand
• # 4 Bora Bora

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Day Trips in Massachusetts: Hikes, history, ice cream and unofficial hot dog tours

'Day Trips in Massachusetts' was written by WBUR and New England Public Media journalists.

For fabulous things to do each week in western Massachusetts, sign up for NEPM’s weekly  Culture To Do newsletter . Every Wednesday, you’ll find recommendations for performances, exhibits, festivals and activities.

For wicked sweet tips for how to make life — and weekends — in Greater Boston more fun,  sign up for WBUR's Weekender newsletter .

Welcome to the Bay State. Home to Boston, the educational, business and cultural epicenter of New England. The state capital gets a lot of shine from guests, of course, but our tiny commonwealth is jam-packed with wondrous places to visit in and out of the city.

As New England's most populous state, Massachusetts has so much on tap to entertain locals and visitors alike: vibrant history, lively city adventures, beautiful hiking, delicious food, academia galore and quite a bit of idyllic rural charm.

For such a small state, Massachusetts has several parochial personalities and subcultures. We could spend pages and pages describing them all, but instead chose to wrap our highlights into four main regions: eastern Massachusetts, Cape Cod and the Islands, central Massachusetts and western Massachusetts.

No matter where you venture in the state, there are bountiful options to satisfy everyone.

Jump to: Western Mass. | Central Mass. | Eastern Mass. | Cape Code and Islands

Western Massachusetts

Four counties — each with a distinctive vibe — define the cities, towns and rural reaches of western Massachusetts. Travel around Hampden, Hampshire, Franklin and Berkshire counties and you’ll see the geological and human-made wonders of the Connecticut River Valley. You can visit the remnants and reimagined uses of the industrial age — now breweries, housing and modern manufacturing. Art and culture venues are everywhere. Colleges and their students abound, offering many interesting events and institutions only a college town can provide. The music halls of Northampton are storied, as are the summer performances at Tanglewood and Jacob’s Pillow . Generations of farms have thrived and grown produce in the region’s rich soil, now alongside new farmers adding to a dynamic food scene .

While some will continue to debate where western Mass. begins , take our word for it! NEPM is based in Springfield — the state's third-largest city — and covers and broadcasts to the remarkable communities that make up the fabulous 413 . Structure a road trip on our historic and scenic byways , or build a route using our day trip picks below.

What to do if you’re a ….

Nature lover.

Climb the highest heights:  At 3,491 feet, Mount Greylock is the tallest peak in Massachusetts. It’s on the Appalachian Trail, but if you don’t feel like hiking, you can drive to the summit (during warmer months) where you’ll find Bascom Lodge and the War Memorial Tower. Unlike most ranges, which run from north to south, the expansive seven-mile mountain ridge of the Mount Holyoke range runs east-west. One option, head to the summit of Mount Holyoke (there are several named summits) and look for the Connecticut River’s oxbow in Northampton. You'll be putting eyes on a view that inspired a 19th century work of art worthy of the Metropolitan Museum of Art in New York.

Across the river is Mount Tom in Holyoke, a great hike to spot hawks making lazy circles in the sky. Its peak is famous among paragliders for having some of the best flying conditions in the world . In Great Barrington, Monument Mountain has several trails, with a 1,642 foot summit. Among the ways to the top, you'll find Mohican Monument and Indian Monument trails, which were recently renamed , by request of the Stockbridge-Munsee Band of Mohicans. Whatever path you take, at the highest point, you’ll have a stellar view of the Housatonic River Valley below.

Green spaces and water finds : Take a stroll along the region’s many accessible trails and wildlife sanctuaries. Among them, Arcadia in Easthampton is fabulous for birdwatching . In nearby Hadley, there’s an accessible boardwalk loop at the Fort River Trail , part of the Silvio O. Conte Wildlife Refuge. For an urban oasis of natural beauty, meander through Springfield’s Forest Park — and check out the Tuesday farmers market, which runs May through October. You should also see the beautiful Springfield Cemetery, hidden off Maple Street in the city’s South End.

• For swimming, numerous freshwater lakes, including Upper Highland Lake within the Daughters of the American Revolution (DAR) Forest, are managed by the state Department of Conservation and Recreation, and a few by local towns. And there’s so much  kayaking and paddling  possible along the Connecticut River  and its tributaries .

Explore on two wheels: Former train tracks turned into rail-trail routes connect several points around western Mass. The 9.5-mile Manhan Rail Trail runs from Southampton to Northampton. That connects bikers (or walkers and runners) to the Norwottuck Trail, which crosses the Connecticut River, heading 11 miles east, from the Damon Road parking lot in Northampton to Belchertown. Farther west, the Ashuwillticook Trail in Adams goes for almost 14 miles.

Geological wonders in the midst:  The Trustees of Reservations oversee many natural areas in the state, including the Chesterfield Gorge , a rocky canyon cut-through by the Westfield River. Fantastical glacial potholes in Shelburne Falls are riverbed remnants of the glacial melt that created the Connecticut River Valley. In Holyoke, along Route 5, find yourself face-to-face with actual dinosaur footprints . In Turners Falls (one of the villages of Montague), Jurassic-era armored mudballs can be found at Unity Park, which is also near the site of a historic surprise attack and massacre in 1676 on a Native American encampment. While in Turners Falls, head to the Great Falls Discovery Center , the canal bike path and two unique stores: Loot , an industrial artifacts emporium, and Swanson’s Fabrics .

A meal to write home about:  Up on a mountaintop, The Dream Away Lodge in Becket is a Berkshire legend — Was it once a brothel? In the 1970s, did Bob Dylan really stop in? — where you can dine in a 200-year-old farmhouse with an incredible garden. In Springfield, Liberty’s is known for its Mediterranean meat grinders and the chicken maqluba is a favorite. Nearby, find some good eats from India at Panjabi Tadka on Main Street. For tea drinkers and crepe eaters, sweet or savory, Crepes Tea House in West Springfield is the spot. Also in “West Side,” bNapoli is the place for a true Italian meal or an aperitivo. In Holyoke, check out two institutions: Nick’s Nest for dogs and ice cream, and El Rincón Boricua for a taste of Puerto Rico ; there's a variety of mofongo and also camarones en salsa de ajo and carne frita. Head north for a more intimate meal in Sunderland’s 1867 town hall at the upscale Blue Heron . Dishes are curated with locally sourced ingredients. That’s a bonus for many restaurants in the region. Find them in this guide from CISA, a booster organization for local farms . (Just saying, never, ever pass up the opportunity to stop at a farm stand for local asparagus or in-season strawberries.) With the area’s sizable Polish population, if you’re hankering for golumpki, a bowl of flaczki or pierogi, you’ll find several delis and restaurants. Maybe stop in at Millie’s or Bernat’s Deli , both in Chicopee, or Janik's in Westfield .

On the cold, sweet side:  Among the many local ice cream makers, seek out Batch in Longmeadow and Mt. Tom’s Homemade Ice Cream and Candy Store in Easthampton. Some creamy heaven can be found at Creamy Delights' New York Style Soft Serve in Hadley, on Lawrence Plain Road. At Flayvors , also in Hadley (ice cream parlor hopping, anyone?), you can watch the cows chew their cud while you devour the scoops and sundaes they made possible. Farther west, in addition to serving Madagascar vanilla and dirty chocolate, SoCo Creamery in Great Barrington is the only shop we know of with a set of “ Shakespeare" ice cream flavors, a nod to the theater group Shakespeare and Co., a couple of towns away in Lenox. (Try marzipan date orange zest, yum!)

Bring on the baked goods:  Western Mass. has incredible bakeries, like Hungry Ghost Bread in Northampton. They offer buttery scones and aromatic pies, but the jewel in the crown is really the variety of bread baked daily in a wood-fire stove. Generations of Puerto Ricans have made Springfield and Holyoke home, with standout bread and dessert makers at the Puerto Rico Bakery II on Armory Street in Springfield and, in Holyoke, Old San Juan Bakery on High Street. As for doughnuts, Donut Dip , around since 1957 in West Springfield, is still frying 30-plus varieties in-house, including maple bacon, red velvet, lemon-filled, old fashioned sour cream, twisted crullers and hot cross doughnuts for those observing Lent. Berkshire Mountain Bakery is known for its artisanal sourdough breads and its take-and-bake pizza. (The chocolate bread is also unforgettable.) The bakery is in the village of Housatonic, just a couple of miles from the Guthrie Center , founded by area resident and illegal dumper of garbage, Arlo Guthrie.

Brews and hard cider:  The craft beer trail in western Mass . is long. In Easthampton, within walking distance of each other, New City Brewery and Abandoned Building sit behind a complex of partially renovated mills. Meanwhile, Fort Hill stands in the middle of a field where paragliders occasionally land. If you go to White Lion in Springfield at the right moment, you might spot former UMass star Marcus Camby or any number of NBA greats coming over from the nearby Basketball Hall of Fame . Bright Ideas is at MASS MoCA in North Adams (also in Westfield), where you’re welcome to pair your IPA with a cheese steak or falafel bites from Big Daddy’s Philly Steakhouse , just steps away.

• A decade ago, Franklin County was the heart of hard cider country in western Mass.,  West County  among its top cider markers.  Now  cider gardens (places to drink on premises, not just buy) are  popping up  on farms and orchards. Check out  New Salem  and  Carr’s  cideries.

The quiet type

Book enthusiast:  “Books you don’t need in a place you can’t find.” That’s the motto of the Montague Bookmill , located in a winding, old building complex hanging over the Mill River, also home to other businesses like the adjacent Lady Killigrew Cafe. In Lenox, The Bookstore has been “serving the Community since last Tuesday,” but really for decades. Check out the recent documentary about its charismatic owner. Several wonderful new and used bookstores are keeping readers happy in Northampton and Amherst (e.g., Amherst Books, Broadside, The Raven, Booklink Books). In Springfield, check out Olive Tree Books on Hancock Street.

Historic homes:  Centuries ago, several writers including Herman Melville lived or came to western Massachusetts to pen what became classics. You can take a tour of Arrowhead, Melville’s expansive home and garden where he wrote “Moby Dick,” and rent his study to do a little writing of your own. The home and garden of celebrated poet and recluse Emily Dickinson is in downtown Amherst. Pay tribute to her — and her desk — before heading to the cemetery where she’s buried . The aristocracy that Edith Wharton wrote about (and lived) can be experienced at her home, The Mount in Lenox. Also in the Berkshires , W. E. B. Du Bois’ childhood home in Great Barrington is part of the Upper Housatonic’s African American Trail . You can drive by Theodor Geisel’s home in Springfield, and then you and your kids can revel in his legacy at the Dr. Seuss Museum .

• Not too far away is the  Springfield Armory National Historic Site , the nation’s first armory, which now holds a significant collection of U.S. military small arms and historic archives.

Bridges to cross and one tunnel : Walk across the Connecticut River in Beaux Art style when you stroll along Memorial Bridge from downtown Springfield to West Springfield. In North Adams, Natural Bridge State Park is home to the only natural white marble arch in North America, according to geologists. It’s made of 550 million-year-old bedrock marble, carved into its iconic arch by the forces of a glacial melt more than 13,000 years ago. Cross between South Hadley and Holyoke on the more recent Vietnam Veteran Memorial Bridge (a.k.a. Holyoke Bridge, South Hadley Falls Bridge and County Bridge), built in 1990. You’ll see the power of the Holyoke dam, some remarkable bird life and small crowds of people fishing (for sport, not dinner). If you time it right (May into June), detour over to the fish ladder to watch anadromous fish passing upstream through the lift. See if you can find the eastern entrance to the Hoosac Tunnel , a 19th century engineering marvel, built not without tragedy . It’s off Route 2, which, on a clear day, offers unbelievable views from the summit point in Florida.

Theater-goers:  A history of summer theater has been bringing actors and other city dwellers to the Berkshires for almost 100 years (and to the porch of the Red Lion Inn ). Add to that several next-gen theater productions happening in Pittsfield, Lenox and other Berkshire towns. Check out stage offerings at many small theaters near Springfield and Amherst, and make sure to look up The Chester Theater , Double Edge and WAM .

Music, dance, film:  In addition to the incredible offerings at Tanglewood, Jacob’s Pillow and MASS MoCA (including the Solid Sound festival , every other year), make sure to look up what’s happening at smaller clubs and halls. Check out The Foundry in West Stockbridge or the reopened Iron Horse in Northampton, Bombyx in nearby Florence and other Northampton area spots. Greenfield has a slew of regular performances at Hawks & Reed , as does The Drake in Amherst. For jazz, it's Watermelon Wednesdays in West Whatley and Dewey’s Jazz Lounge in Springfield on Worthington Street, across from Theodore’s Blues, Booze and BBQ .

If Latin American music is the beat you dance to, Salsa and Bachata nights are a regular thing at breweries, American Legion halls and in Northampton at the E.J. Gare Plaza , tucked between Herrell’s Ice Cream and Tellus & the Satellite Bar (more dancing in their “part-time nightclub”).

On a clear summer night, you can catch a movie outdoors at the Northfield Drive-In (which is technically over the border in New Hampshire, but we're claiming it anyway). Bad weather? Head inside to see curated indy, vintage and arts films at Amherst Cinema , Images Cinema in Williamstown and Pothole Pictures in Shelburne Falls’ Memorial Hall.

Visual art, museums, historical societies:  The Massachusetts Museum of Contemporary Art ( MASS MoCA ) in North Adams is even more worth the trip when you take beautiful Route 2 and travel slowly around the hairpin turn before descending into town . The iconically American artwork of Norman Rockwell can be found at his museum in Stockbridge, and then head north on Route 7 to the Clark in Williamstown, known for its collection of French Impressionism and notable traveling exhibits.

In Holyoke, the International Volleyball Hall of Fame is a stone’s throw from the city’s Children’s Museum (there’s a carousel outside toward city hall). Nearby, in Indian Orchard, you can visit the Titanic Historical Society . Hidden in plain sight is Springfield’s recently renovated Pynchon Plaza — a tiny park of public art, with steps that take you between Chestnut and State Street.

In the Amherst area, a collection of 10 museums is part of the Five College Consortium (maybe you’ve heard of them? UMass Amherst, Smith, Amherst, Hampshire and Mount Holyoke colleges). Historic Deerfield is a preserved 18th-Century New England village that recently broadened how it tells its history to include more about the Pocumtuc tribe that lived in the area before settlers arrived. If you’re interested in fossils — beyond finding them on Route 5 in Holyoke — head to the Beneski Museum of Natural History at Amherst College (apparently the first-ever dinosaur tracks were found in the Connecticut River Valley). The Eric Carle Museum of Picture Book Art is adjacent to Hampshire College (and near Atkins Market — mmmm, cider doughnuts). A few minutes away on foot is the Yiddish Book Center. A place for more than a million of volumes of rescued Yiddish books, plus other historic artifacts like typewriters, the center also has a thorough exhibit on the history of Yiddish language and culture.

A bit north and east, the Swift River Valley Museum in New Salem tells the story of four towns — Dana, Enfield, Greenwich and Prescott — that were taken by eminent domain in the 1930s to build the Quabbin Reservoir .

Central Massachusetts

You’re entering “the heart of the commonwealth,” the cutesy moniker given to Worcester — the state’s second-largest city — as a nod to its geographic centrality between Boston and Springfield. While Worcester may exceed or fall short of your expectations of its other tongue-and-cheek nickname, the “ Paris of ’80s ,” it’s a Gateway City that has historically invested in the arts, a thriving underground music scene and a litany of gorgeous public spaces. And in recent years, a focus on revitalizing its downtown has attracted restaurants, breweries, bakeries and stores — while bringing new patrons to some of its most beloved businesses.

Today, there are ample activities for any day-tripper to fall in love with the city and the many more communities that make up central Massachusetts.

For your planning purposes, the region includes all of Worcester County, and roughly — perhaps controversially — fewer than a dozen or so municipalities that sit in the northwestern shoulder of Middlesex County.

Spanning north to south ‘round the state’s middle like a wide ribbon, the region is polka-dotted with rural or urban sight-seeing options — plus parking that’s almost always cheaper than in Boston. If you’re trying to bop about the towns, traveling by car is quickest. However, two regional transit systems provide routes in and out of Worcester or Fitchburg/Leominster . If you don’t want any funny city business, the region lets you escape into the breathtaking wild, without forcing you to hike anything too hardcore.

If you’re more of a hip, Atlas Obscura adventurer, quick stops for quirk abound! Like this giant chair in “Chair City” Gardner , the city’s nod to its bygone era of furniture making. Perhaps you’d like to delight in examining a huge rock on Main Street in Fitchburg , whose preservation story is thick with irony. (It was apparently strategically exploded in order to exist forever.) Or, maybe you’d like to riffle through treasures — or rust-covered oddities — at a gruffer sort of vintage shop in Leicester.

Point is, there are many ways to keep your day trip poppin’, and we’ve tried to pick a few gems a little farther off the well-worn paths.

Rock your world: Put on decent walking shoes and tread carefully down into the eye-popping geologic wonder of Purgatory Chasm , a state park down Route 146 in Sutton. Its attractions include both mysterious (and problematic ) lore, but scientists think the imposing boulder-filled, quarter-mile chasm formed about 14,000 years ago. That’s when a super tall glacier is said to have suddenly spit out a surge of water, creating a ravine that today people — athletic or not — can play pretend parkour within. Most can navigate the rocks without issue — many a small child in Crocs have conquered them — but folks of all ages ought to avoid hubris , as injuries do happen. (PSA: In bad weather or even after a day of heavy rainfall, it’s best to skip out, as the rocks get dangerously slippery.) Once through its rocky center, you can also stroll along a few short and pleasant woodland trails. And back near the entrance, families often picnic. The park closes for winter and charges for parking from mid-May until late October ($5 for residents; $20 for non-residents).

• If you super dig rocks but want a more modernity-meets-nature setting, head instead to Fitchburg. Intrepid hikers can summit Rollstone Hill to look out at the city and all the old pines that surround it. That is, if you’re not too preoccupied by the scene at your feet:  Hunks of graffiti-covered granite  from a defunct quarry.

Do go chasing waterfalls: Spread across more than 150 acres, The Cascades in Worcester, Paxton and Holden offers a few somewhat challenging hikes that bring you past vernal pools in the springtime. Cascading Waters , as a prominent section is called, features a gentle waterfall that feeds into Cook’s Pond and greets you from Cataract Street in the city. (The waterfall sadly can fade into a trickle if you don't catch it in rainier weeks.) Some of the marked trails are quite steep , but adults and kids alike often manage and get to spy an abundance of native plants and mushrooms along the way. Keep in mind the waterfall looks most impressive after a decent rainfall.

• If you’re interested in other waterfalls across the state, a project called New England Waterfalls lists and rates  dozens of cascades here .
• If you can’t get enough of nature, Hike Worcester, a project by the Greater Worcester Land Trust, offers  this 2022 comprehensive guide , complete with useful trail maps and top-notch hikes around the city and its surrounding towns.

Peak outdoor power: In every season, nature lovers looking to maximize options for fun can find endless activities at these two enormous state-run parks: Wachusett Mountain State Reservation in Princeton and the Leominster State Forest . If you’re bold and fit, Wachusett maintains lovely trails to its summit. But those who want to view the valley below (or even sometimes Boston) from its 2,006-foot peak without sweating can drive up the mountain from around Memorial Day to mid-October. In the winter, many families enjoy cross-country skiing trails or hitting the slopes . Leominster State Forest draws folks looking to not only hike, but also fish, rock climb, mountain bike or swim. You can’t take a dip anywhere in the forest except for Crow Hill Pond, which has picnic areas and a skinny beachfront. However, you may fish and pull the boat into the waters at Paradise Pond. And while we can’t guarantee you’ll spot Bigfoot in these big ol’ woods, some folks really believe you just might .

Dare to be hot doggin’:  OK foodies, I know what you’re thinking. Hot dogs aren’t exactly Michelin star fare. But, our preferred split-top hot dog buns qualify as regional cuisine. Born out of practical need, you may be as surprised as this person (excuse the curse words, please) to learn the rest of the U.S. appears to risk their toppings with different buns. Of course, not all of these beloved central Mass. eateries keep their buns New England-style, but a hot dog tour is nevertheless in order as day trips demand a quick bite.

• First up are a couple local institutions that keep service no-frills and old-fashioned. As the  Gardner News reports , locals love  Lee’s Hot Dog Stand  in Templeton (Baldwinville). The hot dog recipe has been unchanged for more than 50 years, and you should try one “with the works,” aka mustard, onions and relish. In Worcester,  George’s Coney Island  has been a family-owned fixture for more than 100 years. You can’t miss its iconic neon sign of a hand squeezing a hot dog with mustard spilling out. People flock to its wooden high-back benches — which locals have carved their names into — for soft-bunned tasty dogs, with many opting for the restaurant’s “signature chili” on top. “The works” here adds onions and mustard to the chili.
• Hoping to eat a great hot dog in a more rural or roadside setting? Try  Hot Dog Annie’s  in Leicester or  Murph’s Hot Dogs  in Lancaster. Lines often stretch past the door of Annie’s little red shack, with most customers raving about Annie’s secret barbecue sauce, which workers describe as sweet and onion-y. And a great hot dog is one thing, but as  WBUR previously reported , regulars at Murph’s roadside trailer also come for the fun of talking with the proprietor.

Crack open some craft beers: There’s no shortage of craft beer spots in Worcester; here are just a few. It’s a hop-head paradise with Greater Good Imperial Brewing Company ’s taproom and kitchen (many of the beers are a bold 8% or higher and the noshing menu is robust). If not everyone in your party is a drinker, Redemption Rock Brewing Company stacks its menu with beers and hard seltzers, and also mocktails, lemonades and a full coffee/espresso bar. Plus, well-behaved doggos are welcome inside, too. Finally, near the storied and now-updated Kelley Square rotary, Wachusett Brew Yard offers handcrafted ales and lagers you can sip while eating something delicious from the international food hall it sits beside.

• Thriving for more than a decade now, the region’s arguably most famous beer haven is  Tree House Brewing Company  in Charlton. With several locations across Massachusetts, it’s maintained a  cult-like following , in part over its hazy New England IPAs. Its Charlton taproom is its largest, with the company’s widest selection of craft beers and cold brew coffees, and plenty of seating outside and indoors. The owners recommend  weekday visits  if you hate long lines.
• For anyone who wants a beer after traveling back in time at the living museum, Old Sturbridge Village, its picturesque host town has two breweries worth checking out.  Rapscallion Pub  invites you and your dog to its outdoor patio and offers lots of from-scratch vegetarian menu items. Meanwhile,  Altruist Brewing Company  has two riverfront beer gardens and is situated within a mill building that's more than 160 years old.

Diner car destination: Brunch options can make or break a community’s character. For central Mass., an embarrassment of classic diner rail cars has imbued the region with a small-town charm that suggests patrons might even like that the waitress delivers pet names alongside bottomless coffee. So, honey, how did we get so blessed with classic boxcar breakfast joints? According to the Worcester Telegram & Gazette , it’s because the city was once home to a major manufacturer of them: the Worcester Lunch Car Co. Today, several of its diners still operate in its namesake city, across New England and beyond. To experience the cars or similarly fashioned diners in Worcester, try Miss Worcester Diner (cash-only), Lou Roc's Diner (outdoor seats in nice weather), Marvin’s Corner Lunch (the tasty, cheese-covered Kelley Square special might require a post-breakfast nap), Ralph’s Rock Diner (an eatery and 21-plus event space for local live bands, trivia and comedy open mics) or Boulevard Diner (open nearly 24 hours on Thursday through Saturday). Blue Moon Diner in Gardner is another central Mass. Worcester Lunch Car Co. option to check out, as well as Charlie’s Diner in Spencer.

Gaming enthusiast

A stacked barcade:  Looking for a lively and affordable spot to drink with friends while bouncing between nostalgic arcade machines and modern “rhythm” games? Freeplay Bar and Arcade in Worcester charges a flat rate ($7 on weekdays; $12 on Fridays and Saturdays) for full access to its near endless array of tabletop or traditional coin-op machines. This 21-plus spot that's open daily past midnight lets you stake out old-school staples like Tetris and Ms. Pac-Man, or get the blood flowing by bashing on pinball machines, hopping to the beat with DDR Extreme or challenging your pals on one its three air hockey tables. There’s an outdoor patio where you can cool off if the crowded room gets too warm or you need to decompress after failing to beat your own Galaga record.

A Gateway to Windows of gaming:  If you love PC games or can’t log enough hours on the Nintendo Switch, but want to be a tad more social, head to All Systems Go Esports Facility in Worcester. The space boasts 40 “high-end” PCs (complete with fancy chairs) that offer a suite of pre-loaded games or internet access to your subscription-based gaming systems. It keeps four Switch consoles on deck so you and up to five of your pals can play pretty much every Mario game you can think of for $20 per hour. And in what feels like concessions built for serious gaming, the place lets you eat its pizza, wings or loaded fries at its computers (if you promise to be neat about it) and has an “Energy Bar” with specialty Red Bull-infused cocktails and non-alcoholic Red Bull tea drinks. For folks who want to get away from screens, the facility also lets you pick from more than 50 card or board games.

Escape from it all, if you can:  Puzzle masters, rejoice! You can decipher hidden clues at The Gate Escape in Leominster (children ages 12-15 can play under adult supervision). If the love of your life really loves a good mystery, the staff will even let you hide a ring and propose inside. Playing with a larger party? Try Escape Games Worcester , which ideally fits about six to eight riddle-solvers in your private escape room (but might let you add a couple players if you ask nicely). The business allows walk-ins, but recommends you book in advance; kids 9 and older can play. It brags that its puzzles are challenging, claiming roughly a third of teams free themselves on time. Born from the mind of a former TV/film set decorator, Curious Escape Rooms in Fitchburg says its team puts serious effort into setting up unique puzzle rooms, adding it may be the only place that puts players inside a dollhouse.

Eastern Massachusetts

Eastern Massachusetts is the densest part of New England by a lot of definitions: It's the most populous area, the most built-out, and has more things to do per-mile than most other regions in this guide.

There's so much happening here, locals more often refer to the smaller regions inside(ish) it. There are the North and South shores, which to an untrained eye look alike but to a Masshole are completely different planets. Along the New Hampshire border lies the Merrimack Valley, whose glory years as an industrial powerhouse have given way to revitalization around history and art. Out to sea are the Harbor Islands, tiny little jewels perfect for exploration and picnicking. And farther inland sits MetroWest, a hodgepodge of suburbia, corporate headquarters, thickets of woods and lots of trails to explore.

If you're coming from out of town, chances are you've thought a lot about what to see and do in Boston. And that's great; we offer some suggestions along those lines below. But don't sleep on Boston's vibrant, idiosyncratic and welcoming neighborhoods , where you can avoid throngs of tourists and instead try the food and music and cultures that gives this city its energy.

Since Boston is the hub (see what we did there?), highways and transit lines fire off in almost all directions (sorry, you can't take the T to the Harbor Islands). That makes for easy day-tripping, with or without a car.

What to do if you're a...

First let's go to the swamp. OK, it's a marsh: Nestled between East Boston and Revere is one of the area's best-kept secrets. Belle Isle Marsh is an urban wetland that provides excellent opportunities for trail walks and birding. It also lends itself to more day-tripping fun thanks to its proximity to the MBTA's Blue Line. Hop the line north for a reverie on Revere Beach, or head south to Eastie's Maverick Square and walk to Pier's Park to get a gorgeous view of the downtown skyline across the inner harbor.

Whose woods these are I think I know: If you're looking for a more woodsy adventure without alighting for New Hampshire's White Mountains, the Middlesex Fells offers great trails for walking and cyclists alike (even if they don't always like each other). Pack a picnic, try some kayaking, bring your fur baby for some good ( permitted !) off-leash walking, among the other options available. Public transport is a little trickier here, but the Orange Line's Oak Grove stop is a 15- to 20-minute walk, and there are three bus routes. There's also parking at several locations along the 2,200-acre reservation.

Live deliberately and maybe catch a swim: Nestled on the edge of Concord, Walden Pond scratches a lot of rustic New England itches. There's the romance of Thoreau's effort to "live deliberately" along its waters, the beauty of the surrounding Adams Woods and Pine Hill, access to American history with the nearby battlefields for Lexington and Concord, and a unique art experience down the road at Lincoln's deCordova Sculpture Park and Museum .

Bike to the sea: The Northern Strand Trail , connecting Somerville to Lynn (and then by surface streets to Nahant Beach), has been decades in the making and will take you through all sorts of scenery, from the casino glitz and industrial decay in Everett to the edges of the beautiful Rumney Marsh in Revere, to the leafy suburban streetscape in Saugus. It's a long haul but extending your ride to the Lynn (interim) commuter rail station can mean a transit-aided ride back.

Thar she blows: Bike trails, pond hikes, birding. Many of the above options take a little stamina to complete. But if you can't — or don't want — to sweat while enjoying nature, try a whale watching tour. With boats that leave both Boston and Gloucester, you have options for your departure. And depending on where the whales decided to while away their day, you could end up deep into Massachusetts Bay, sometimes within sight of Provincetown. This is also a great option during one of Boston's increasingly muggy heat waves, since the air over the water is significantly cooler. When you're out there, watch for some tell-tale signs while scanning the water: Look for plumes of mist coming from blowholes, sea birds sitting and diving in the middle of nowhere, and the occasional whale leaping into the air during a breach.

It's not just witches: Most people pile into Salem in October for its sPoOoKy vibe, because the tides of time have eroded the harder edges of that awful period in witch-hunt history. But there's lots to do and see, both tourist-y and and more respectfully, about not just the trials but of the area's nautical heritage, literary bonafides and overall beauty. The downtown is served by the commuter rail and is a walk-and-shop pleasure, dotted with local artisans and noshes. Closer to Derby Wharf you can check out the House of the Seven Gables and enjoy a little olde-with-an-e time candy before hitting some of the more contemporary dining and drinking options.

Defend Boston! And then maybe have a snack: Georges Island in Boston Harbor is great for picnics and has a big honking fort to explore. Built in the 19th century, Fort Warren was a training ground for Union soldiers heading to battle during the Civil War. If you're from here, there's a very good chance you took a field trip to explore its now-abandoned battlements, and the dark passages inside, so if you're bringing the kiddies, maybe stick with the ranger tour. Outside the fort, unwind and unwrap your own sandwiches or make a trip to the snack cart .

A man, a plan, a canal: Lowell? : The name may scream Rhode Island to you, but the Pawtucket Canal Boat Tour is a great way to explore Lowell, perhaps the most emblematic former mill town in Massachusetts. Dug to take advantage of the Merrimack River during the Industrial Revolution, the city's canals now offer a great way to explore the textures of its textile history before disembarking and exploring the rejuvenated downtown.

The field trip favorite: For lots of adults in this region, a cherished memory was taking a field trip to the then-Plimoth Plantation. To move away from its Euro-centric view of the past, the museum has since spent years trying to incorporate more input from the Mashpee Wampanoag tribe to include the 10,000-plus years of history that came before the Pilgrims bumbled into this area. If you haven't been there since you were a kid, you can still see the colonial village, but there's much more to explore today with the Historic Patuxet Homesite. The site's name change in 2020 was intended to be reflective of this more representative — and accurate — historical account, though some Wampanoags say there's still more work to be done .

Family Trip Planner

Old time fun: Look, everyone loves Disney World and Six Flags, but sometimes you don't want your entire day to feel that extra. Sometimes, you want a place like Salem Willows , which combines a waterfront park with an arcade, bumper cars and boardwalk-style dining options like pizza, fried clams or ice cream. And despite fears that it would go away, Salem Lowe is still there offering its legendary — or infamous — chop suey sandwich .

A block for kids: If you're in Boston with the kiddos, plan to hit this can't-miss doubleheader. Situated on either side of Fort Point channel, the Boston Children's Museum and Tea Party Museum is an easy and fun day out. The Children's is famous for its interactive exhibits, so be ready to play. And if your tykes need a little transgressive release, telling them they're allowed to throw crates of tea into Boston Harbor is too tempting to pass up.

Cool treats and fresh farm air: If you're looking for something a little more pastoral, you can't go wrong at some of the open farms in the area, like Kimball Farm in Westford . Grab an ice cream, hop on a hayride, take a trek on a pony, and grab a bat or golf club at the cages and ranges. Or, if you time it right, you can get some to-die-for fresh cider doughnuts in the fall.

Some low-hanging fruit: Apples aren't the only thing you can pick as part of a fun day out. Ward's Berry Farm in Sharon gives you a chance to harvest strawberries fresh from the bush. You can bag up a bushel of the berries (and yes we're calling them berries we don't have time for your internet-fueled pedantry ). If you can’t get enough plucking edibles or florals from the dirt, Ward’s lets you run wild on its other varieties of fruits and vegetables, as well as its tulip and sunflower collections. You can also just go and enjoy a day of corn maze-running and hayride-riding.

Cape Cod and Islands

New York has the Hamptons. New Jersey has the shore. And here in Massachusetts, we've got the Cape and Islands.

The Cape’s arm-shaped peninsula boasts 550 miles of unspoiled coastline, maritime character and seafood galore, making it a tourist hotspot every summer. In the 70 miles from the Cape Cod Canal to Provincetown’s Race Point beach, there are 15 towns, each dazzling visitors with their own unique beach town vibes. In the fall, the Cape quiets, offering a cozy and quintessential New England ambience, too.

Where exactly and when you visit these coastal havens depends on what you’re looking to do. But first, you must cross one of two bridges: the Sagamore to the north or the Bourne to the south. Deciding which to take depends on where you’re headed.

Sandwich, the first exit off the Sagamore, offers a quieter coastal experience best known for its recently rebuilt boardwalk. A little farther down 6A, you’ll hit the summer tourist magnet Falmouth. Beyond its lively downtown, visitors are often attracted to its famous annual road race . Head to Chatham and you’ll find narrow streets, lots of seals, the Cape Cod Baseball League and high price tags on, well, everything. In Wellfleet, catch a flick on Route 6 at one of the country’s remaining drive-in movie theaters. Provincetown, despite being farthest down Cape, is one of the more convenient destinations to day trip from Boston because there’s a ferry. The area is a longtime LGBTQ+ and artist sanctuary that's increasingly known for its nightlife (we love a flawless drag show ). Just be warned crowds balloon in P-town each year during Bear Week , Provincetown Carnival and Family Week .

To explore Martha’s Vineyard or Nantucket, take a ferry or perhaps find a friend with a big enough boat . Several passenger-only ferries will ship you to the Islands, like the Island Queen from Falmouth to Oak Bluffs on Martha’s Vineyard and the Freedom Cruise Line from Harwich Port to Nantucket. If you want your car, the Steamship Authority is your best bet for either island. However, car reservations must be made in advance, and wintertime slots often fill up. But if you’re willing to travel on non-peak days, hop on a waitlist; you may be in luck. Ditch the wheels and you can walk on the Steamship Authority’s boats without booking ahead.

If you're looking for bustle, Martha's Vineyard brims with activities for beach bums, foodies or families. Just a 45-minute ferry away, the island offers reliable public transit by bus that hits all its major points. Meanwhile, Nantucket's tinier landscape offers postcard picturesque scenes with fewer crowds but tamer recreational choices. Both places can boast about gorgeous beaches — and even presidents love the island vibes.

Ride a bike: A great way to explore Cape Cod is by bicycle. The 25-mile-long Cape Cod Rail Trail is the region's best-known bike path. It winds between Yarmouth and Wellfleet, passing through Nickerson State Park, Cape Cod National Seashore and lots of little downtown areas. Another option is the Shining Sea Bikeway , which extends for 10.7 miles from Woods Hole to North Falmouth. (Pro tip: If you start in North Falmouth, you can jump off for a quick, summertime taco break at Quicks Hole Taqueria in Woods Hole.) For a straight-shot ride with constant water views, check out the Cape Cod Canal Bikeway . With entrances in Bourne or Sandwich, the two seven-mile paved trails run on either side of the canal. Though they're often slammed in the summer, bike rental stores are everywhere. (Some shops only allow week-long rentals, so check online and plan accordingly.)

• A  very extensive bike trail  on Martha's Vineyard will take you almost anywhere on the island.

Hit the beach: The Cape Cod National Seashore prides itself on over 40 miles of protected pristine beach, marshes, ponds and woods. It’s an outdoor-lovers' paradise. Check out the National Park Foundation’s guide to area beaches to learn more about where to go, seasonal fees, accessibility and even sharks . U.S. News and Travel also keeps a good list of popular Cape beaches (and the first choice, Mayflower Beach in Dennis, is a favorite for WBUR's assistant managing editor of newsletters, because during low tide you can walk for miles along tidal pools).

• If you drive to the Cape, you can reimagine your beach day by off-roading. There is an off-road vehicle corridor at the Cape Cod National Seashore, but keep in mind that park rangers tend to be strict about fire and grilling rules. You can get the most of your  off-roading beach day at Sandy Neck , a six-mile long barrier beach in Barnstable. Bring a grill, pack a cooler (of the non-alcoholic variety), set up a fire at night and even spend the night if you have a sticker and decide to make a weekend of it. The only downsides of Sandy Neck is the beach is rocky and you need to be aware of plover-related closures.

Remarkable creatures: Woods Hole, technically census-designated as part of Falmouth, is home to an Ivy League-level marine biology research center: The Woods Hole Oceanographic Institution. The private nonprofit is a pretty big deal — I mean, they helped find the Titanic — and you can get a peek into their work with their weekday tours (definitely book in advance).

• If you'd rather look to the sky for feathered friends (or want an option closer to P-town),  Wellfleet Bay Wildlife Sanctuary  contains nearly 300 bird species within its five miles of trails. As you wander through a salt marsh, barrier beach, pine woodlands and a pond, bird watchers should be on the lookout for green herons, orchard orioles, eastern bluebirds and black-bellied plovers.

Fish of the sea:  There are plenty of places to get your seafood fix down the Cape. (Seriously, it’s hard to choose.) But one award-winning spot for a cup of clam chowder is Skipper Chowder House in South Yarmouth . Restaurant-goers describe it as creamy and rich, and most importantly, packed with fresh clams. Sit on its deck overlooking the water and enjoy. You can hit up many other fried clam shack joints along the Cape where you can embrace the "belly or bust" clam-eating life. If you want to do a side-by-side comparison, there are two hotspots in Dennis: Captain Frosty's and Kream n' Cone . To break out of the Dennis shell, try Arnold's Lobster & Clam Bar in Eastham ('50s diner, "Happy Days" vibes), Mac's Chatham Fish & Lobster in Chatham (gluten-free options) and Seafood Sam's (it's got two fast-casual locations, one in Falmouth and one in Sandwich with some serious views overlooking the Cape Code canal).

For lobster, it's a no-brainer to head to the Lobster Pot on Commercial Street in P-town. Since 1979, the iconic establishment has been slinging lobsters — pan-roasted, baked, stuffed, boiled and nestled in a toasted roll, lightly dressed in mayo, as our fishermen forefathers intended. Its neon sign draws locals and tourists alike. Save room after your seafood feast and walk along the crowded street to the legendary Provincetown Portuguese Bakery , which is over 100 years old, for sweet treats like pastéis de nata — a flaky, custard pastry that's simply dreamy. If you're just driving through the Cape to catch a ferry, a great pit stop is the Seafood Shanty in Buzzards Bay. The lobster rolls are so packed that some suggest splitting one between two people and asking for an extra toasted roll.

• If you have access to a kitchen and want to cook for yourself, head to the  Chatham Fish Pier Fish Market . Not only will you get to watch local fishermen unload their catch of the day, but you’ll have an ocean's worth of fresh seafood options. The market's take-out menu also offers the classics: fried whole belly clam and lobster rolls.

I scream, you scream, we all scream for … After a hot day at the beach, nothing beats ice cream for dessert. One of the most popular spots is Sundae School. Open since 1976, Sundae School now has two locations — Harwich and Dennisport — and a cult-like following for its small-batch flavors and high butterfat content. If you don’t believe us, the shop has been given accolades in numerous publications, including Boston.com , The Boston Globe , USA Today , Food & Wine and The Cape Cod Times . Other fan-favorites for a scoop — or three —include Twin Acres in Sandwich; Smitty's in East Falmouth, Mashpee and Barnstable; Cape Cod Creamery in Dennis, Hyannis and South Yarmouth; Four Seas in Centerville (which was recently listed for sale, but we hope stays just as good); and Ice Cream Cafe in Orleans. On Martha’s Vineyard, you can’t go wrong with Mad Martha’s, with shops in Edgartown, Oak Bluffs and Vineyard Haven.

Cranberries, everywhere: If you visit the Cape in the fall, you’ll be treated to a crimson feast for your eyes. One-fifth of the nation's commercial cranberry crop is grown in the Buzzards Bay region, according to the Buzzards Bay Coalition . Wade into the blazing red colors on a tour of one of the many local bogs . If you want a DIY-experience, take a walk along the Pamet Cranberry Bog Trail in Truro. It weaves between woods and sand dunes, and in the wooded part there’s a short loop to an old cranberry bog house that is pretty neat.

• If you'd rather eat your berries than learn about them, head to Hearth N' Kettle in South Yarmouth and Hyannis (order the cranberry oatmeal pancakes, part of the Mayflower breakfast) or Somerset Creamery at any of its three locations — two of which are in Somerset and one in Cataumet — for a scoop of "cranberry bog" (dried cranberries, walnuts and dark chocolate mixed into a cranberry ice cream).

Lighthouses galore:  There are 14 beacons across the Cape’s coast, many of which are historic and offer tours. Why so many? Well, before the Cape Cod Canal was built in 1914, ships sailing along the northeast had to go all the way around the tip of the Cape. The National Park Service, which operates the Cape Cod National Seashore, says during those early times there were more than 1,000 wrecks in the waters between just two of the Cape's outermost towns, Truro and Wellfleet. Within the National Seashore’s control, check out Highland Light, in North Truro, Nauset Light and Three Sisters (all in Eastham) and Chatham Light (which remains an active-duty U.S. Coast Guard station).

• Let’s zoom in on those sinking ships for a second. During the mid-19th century maritime era, huts were built with driftwood from shipwrecks among the dunes in Provincetown and Truro in what’s now referred to as Provincelands (nearly 2,000 acres of protected sand dunes that’s now part of the National Seashore). Lifesaving “surfmen” would stock the shacks with food and water so if someone got shipwrecked, they’d have a safe place to ride out the storm. From the 1920s through the 1950s, the area transitioned to become more of a home for artists living in 19 historic shacks that still stand today. Some of their short-term residents include Eugene O'Neill, Jackson Pollock, Norman Mailer, Jack Kerouac and Tennessee Williams. However, in recent years, there's been  tension on the Cape as the National Seashore has forced long-term shack residents and artists to leave .

Honoring native land:  The Wampanoag Tribe of Gay Head (Aquinnah) on Martha’s Vineyard became a federally acknowledged tribe in 1987. Its tribal lands include Gay Head Cliffs, Herring Creek, Lobsterville and parts of Christiantown and Chappaquiddick. The tribe offers a recommended self-guided tour here , that takes you past cranberry bogs and the impressive Aquinnah Cliffs. Grab a snack at Alley's General Store in West Tisbury.

• Speaking of Aquinnah, the historic Gay Head Lighthouse — which weighs 400 tons — was  actually moved  about 130 feet away from an eroding cliff.

Early settlers: Head to Provincetown to see the Pilgrim Monument, which was built between 1907 and 1910 to commemorate the first landfall of the Pilgrims in 1620. (It’s a way cooler historic landmark than Plymouth Rock, trust us.) The signing of the Mayflower Compact also happened in Provincetown Harbor. The museum that celebrates this history is charming and focuses on the region’s maritime history.

Out in the deep: Take a ferry to Martha’s Vineyard and check out the “Jaws” bridge. It’s located on Beach Road in Edgartown along Joseph Sylvia State Beach. And while doing this is illegal, for years people have jumped off the bridge into high tide. (We're not your mom or the police, but we'd regret not stressing that you should never attempt this in shallow waters.) “Jaws” takes place on the fictional island of Amity, and was filmed almost entirely on Martha’s Vineyard. Many locals were cast in the movie. In one famous scene, Police Chief Brody jumps over the bridge railing to save his kids. Even if you don’t swim, heading to the bridge is a fun way to experience Steven Spielberg’s iconic film in person. (You probably won't see a shark, but people do spot them along the Cape and Islands' beaches.)

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A New England Traveler’s Guide to Nova Scotia

The best time to explore this delightful Canadian province less than a two-hour flight from Logan? Right about now.

From day trips to weekend getaways, our biweekly Traveler newsletter shows you the best of New England and beyond.

A picturesque scene on the Bay of Fundy. / Photo by Scott Munn/Tourism Nova Scotia

Lots of people know about Nova Scotia’s natural wonders—the world’s most drastic tides, the dramatic cliffs and rock formations. Some even know why Nova Scotia ships us a Christmas tree for the Common every year: In 1917, Boston sent emergency aid after two ships collided in Halifax Harbor, causing the biggest non-nuclear detonation in history. But the tiny Canadian province is also a treasury of architecture, culture, and history. It’s where the Cajun people of Louisiana’s bayous originated and where thousands of Black loyalists were relocated by the British after the American Revolution. It’s home to distinctive lighthouses, a lush wine-growing region, and six UNESCO World Heritage sites. In short, it’s fascinating, beautiful, and well worth a visit, especially in the mild summer months.

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The famed Cabot Trail is Nova Scotia’s most popular tourist route, but a less crowded way to discover many of its secrets is a road trip tracing a loop from Halifax to the south. Before leaving the capital, must-see highlights include the star-shaped Citadel , the hilltop fortress commanding the city; the Maritime Museum of the Atlantic and its unparalleled collection of Titanic artifacts; and the boardwalk that winds along the waterfront. A mere hour to the south is Peggy’s Cove and its famous lighthouse—one of the most Instagram-worthy sites in the region—and another hour-and-a-half brings you to the historic port of Lunenburg . A mix between Provincetown and Bar Harbor, its streets are lined with historic mansions, and the main wharf is home to the legendary schooner Bluenose II , which graces the Canadian dime. Further along the coast lies Birchtown , where thousands of freemen and escaped slaves created the continent’s largest free Black settlement in the 1780s. The Black Loyalist Heritage Centre beautifully conveys this overlooked chapter of history.

The iconic Peggy’s Cove lighthouse. / Photo by Gerald Zaffuts/Getty Images

To experience the ancestral land of the Mi’kmaq in all its unspoiled glory, cut inland and north through the Tobeatic Wilderness Area, designated by the Starlight Foundation as one of the world’s best places for viewing the night sky. Continuing north, you’ll emerge in wine country that’s every bit as beautiful as Napa or Sonoma. The vineyards were originally planted by French settlers who were later deported by the British and relocated to Louisiana, where their “Acadian” identity morphed into “Cajun,” but the same joie de vivre persists in towns like Grand Pré and its eponymous winery. Finally, travel to the Shubenacadie River to go tidal-bore rafting on waves up to 13 feet high, thanks to the Bay of Fundy’s massive tides. There are at least five tour operators from which to choose, and when you’re done, you’ll only be 40 minutes from the Halifax airport.

An expansive vineyard at Grand Pré Wines. / Photo by Patrick Rojo/Tourism Nova Scotia

Halifax is the shopping capital of the Maritime provinces, with chic boutiques like the men’s designer clothing store Duggers (founded by Nova Scotia Sport Hall of Fame hockey player Dugger McNeil), but the best finds are artisanal, locally made handicrafts, including pottery, jewelry, and artwork.

A mouthwatering dish from Beach Pea Kitchen & Bar. / Photo by Shawn Gillan/Beach Pea Kitchen & Bar

Nova Scotia is justifiably famous for its seafood, but there are a few standout restaurants serving other cuisine along this route. In Halifax, Agricola Street Brasserie serves modern takes on all the Gallic classics; the simplicity of the décor at Beach Pea Kitchen & Bar in Lunenburg provides the perfect backdrop for its superior Italian fare. Meanwhile, Le Caveau at Grand Pré Wines is a Wine Spectator award winner and lives up to all the hype.

Just outside the Tobeatic Wilderness Area, Trout Point Lodge is a luxury inn located in the heart of a protected biosphere reserve. It’s the first “Starlight Hotel” certified by Starlight Foundation, with an on-site guide who conducts nightly stargazing from specially built platforms. Other activities include forest bathing, hiking, kayaking and canoeing, berry and mushroom foraging, paddleboarding, and yoga, and a barrel sauna and wood-fired hot tub are perched at the river’s edge. Just be sure to fill up your gas tank before going; it’s truly in the middle of nowhere.

Unwinding in nature at Trout Point Lodge. / Photo courtesy of Trout Point Lodge

GETTING THERE

Air Canada and American both fly nonstop from Boston to Halifax (a sub-two-hour flight), while a ferry runs from Bar Harbor, Maine, to Yarmouth, Nova Scotia, between May and October.

First published in the print edition of the July 2024 issue with the headline, “Nova Scotia.”

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New England’s 16 best beaches for families

We asked beachgoers to reveal their family-friendly favorites, and these are the ones that floated to the top. tell us: what’s yours.

Crane, Good Harbor, Singing, Wingaersheek: Those are the iconic beaches that get a lot of love each year, and for good reason. They’re gorgeous, expansive, and relaxing — if you can get in, that is. Parking requires a strategy, crowds can be intimidating, and greenhead flies are downright painful. What about a few other, lesser-known sandy expanses? I asked beachgoers to reveal their family-friendly favorites, and 16 names floated to the top.

As always: Do your homework before setting out regarding high and low tides, parking regulations, and lifeguard hours.

Cahoon Hollow Beach, Wellfleet : This sandy stretch earns points thanks to The Beachcomber, a family-friendly restaurant right on the water with a large kids’ menu (and live music late into the night, if you have a baby sitter). Pay $30 to park on-site, hang at the beach, and get a voucher toward food and merch. 1120 Cahoon Hollow Road, Wellfleet, www.wellfleet-ma.gov/beaches

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Crescent Beach State Park, Cape Elizabeth, Maine : Minimal crowds, lots of wildlife and tide pools, and easy parking. What’s not to love? (Hungry seagulls, for one thing.) Stop for ice cream at the nearby Kettle Cove Ice Cream and Shack on your way home. 109 Bowery Beach Road, Cape Elizabeth, Maine, www.maine.gov/dacf

Devereux Beach, Marblehead : Regulars appreciate clean facilities, picnic areas, and a friendly snack bar at this low-key hangout. The sand is a bit coarse, but the slides at the on-site playground are smooth. 99 Ocean Ave., Marblehead, www.marblehead.org/recreation-parks-department

Green Harbor Beach, Marshfield : Fans shout out the walking-distance Green Harbor General Store (grab a deli sandwich before hitting the beach) and Green Harbor Lobster Pound (stop for dinner afterward), plus the option to walk all the way to Duxbury Beach if you want to get some steps in — or if you want to escape your kids. Beach St., Marshfield, www.marshfieldpolice.org/marshfield-beaches

Jenness State Beach, Rye, N.H.: Dramatic waves, and the Summer Sessions Surf Shop right across the street offering kids’ and grown-up lessons, make this a prime spot to people-watch. Well-maintained facilities and fairly easy street parking up the road add to the allure. Pro tip: Drive a few minutes north on Ocean Boulevard for the best lobster roll of your life (served on a husky burger bun) at Petey’s Summertime Seafood before heading home. 2280 Ocean Blvd., Rye, N.H., www.nhstateparks.org

Lynch Park, Beverly: This one gets raves for ample parking, soothing surf, outdoor summertime concerts, and an on-site playground and splash pad. 55 Ober St., Beverly, www.bevrec.com/the-park

Mother’s Beach, Kennebunk, Maine: This is where you’ll find me with a trashy novel or a trashier podcast. There’s plenty of free, nonresident parking along the windy roads adjacent to the beach (pretend you own one of the estates nearby); as well as a playground, terrific waves, and plenty of tide pools for crabbing. Visit Bennett’s down the road for an enormous to-go sub — truly, one sandwich could feed three people — before you set up shop. 263 Beach Ave., Kennebunk, www.kennebunkmaine.us/308/Beaches

Nahant Beach Reservation, Nahant : Speedy access from the city makes this “a hidden treasure,” raves one beachgoer, despite the bold seagulls who enjoy swiping sandwiches. Savvy swimmers arrive by 9 a.m. for the easiest parking and leave by noon, before the crowds appear. “We’d go there several days each summer, leave around lunch, and stop at Alive and Kicking in Cambridge for lobster sandwiches” before going home to nap, advises another fan. Nahant Road, Nahant, https://www.mass.gov/locations/lynn-shore-nahant-beach-reservation

Nantasket Beach Reservation, Hull: Fans appreciate the mild surf and clear water (“you can be up to your neck and see your toes,” raves one regular). For maximum nostalgia, the Paragon Carousel is a short stroll away. 212 Nantasket Ave., Hull, www.mass.gov/locations/nantasket-beach-reservation

Old Silver Beach, Falmouth: OK, first things first: The parking lots fill up quickly and is often staffed by beleaguered teens, so arrive close to 9 a.m. or closer to 4 p.m. But once you’re there? Lots of warm tide pools to explore, clean facilities, and the on-site Burger Shack, with a vast menu of snacky classics. 296 Quaker Road, Falmouth, www.falmouthma.gov/151/Beach

Rexhame Beach, Marshfield: Go after 5 p.m. for $5 parking and a sunset scramble in the dunes, which fans compare to those in Truro (minus the traffic). 325 Standish St., Marshfield, www.marshfieldpolice.org/marshfield-beaches

Rock Harbor Beach, Orleans: Regulars appreciate the mellow vibe, drama-free parking (basically unheard of on the Cape) and mile-long, low-tide strolls. Bayview Drive, Orleans, www.town.orleans.ma.us/544/Natural-Resources

Salisbury Beach State Reservation, Salisbury: Americana at its finest: big waves, soft sand, clean bathrooms, and easy on-street parking (especially if you arrive before 10 a.m. or so). Joe’s Playland is nostalgia central, with ice cream, an arcade, mountains of fried seafood, and a new carousel. 15 Broadway, Salisbury, www.mass.gov/locations/salisbury-beach-state-reservation

Salty Brine State Beach, Narragansett, R.I.: This smallish, toddler-friendly beach has manageable waves, soft sand, on-street parking, and a concession stand. Plentiful boats and ferries floating past add to the atmosphere. Go early or late; it fills up fast. 254 Great Road, Narragansett, R.I., riparks.ri.gov/History-HistorySaltyBrine

Skaket Beach, Orleans: This bayside beach has warm, shallow water and gentle waves (your humble correspondent learned to swim here); parents also appreciate clean facilities and outdoor showers. Skaket Beach Road, Orleans, www.town.orleans.ma.us/544/Natural-Resources

Winter Island, Salem: Nothing frightening here, just affordable parking (including for RVs) and serene waves on Waikiki Beach. Bonus: It’s a Salem Trolley stop, if you’re in the mood for sightseeing. Salem Willows Arcade and Park is a 10-minute walk. 50 Winter Island Road, Salem, www.salemma.gov/winter-island-park

Kara Baskin can be reached at [email protected] . Follow her @kcbaskin .

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Verdict Watch: Day 4

Patriots announce 2024 training camp schedule, dates for public practices

Carolina Panthers v New England Patriots FOXBOROUGH, MASSACHUSETTS - AUGUST 19: A view of New England Patriots helmets on the bench during the preseason game between the New England Patriots and the Carolina Panthers at Gillette Stadium on August 19, 2022 in Foxborough, Massachusetts. (Photo by Maddie Meyer/Getty Images) (Maddie Meyer/Getty Images)

FOXBORO, Mass. — The New England Patriots will kick off training camp ahead of the 2024 NFL season in just a few weeks.

Veteran players will be required to report to Foxboro by Tuesday, July 23, with the first training camp practice being held on the fields behind Gillette Stadium on Wednesday, July 24, the team announced Tuesday.

The Patriots will then hold open practices for fans to attend on Thursday, July 25, and Friday, July 26.

All practice times are scheduled to start at 11:00 a.m. with gates opening at 10:00 a.m.

The Patriots also announced that they will hold a joint practice session with the Philadelphia Eagles in Foxboro on Tuesday, Aug. 13, before playing the NFC East team in a preseason game at Gillette on Thursday, Aug. 15.

The entire practice schedule is as follows:

Wednesday, July 24

• 10:00 AM – Gates Open
• 11:00 AM – Practice Begins

Thursday, July 25

Friday, July 26

Saturday, July 27 - NO PUBLIC PRACTICE

Sunday, July 28

Monday, July 29

Tuesday, July 30

Wednesday, July 31 – NO PUBLIC PRACTICE

Thursday, August 1

Friday, August 2

Saturday, August 3

Sunday, August 4 – NO PUBLIC PRACTICE

Monday, August 5

Tuesday, August 6

Wednesday, August 7 - Sunday, August 11 - NO PUBLIC PRACTICE

Monday, August 12

Tuesday, August 13

• 11:00 AM – Joint practice with the Philadelphia Eagles

The team said updates to the training camp schedule will be posted here .

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