road trip from pittsburgh to boston

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Driving from Pittsburgh to Boston -- Recommendations? - Pennsylvania Forum

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Driving from Pittsburgh to Boston -- Recommendations?

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In the first part of your trip, I would suggest visiting Horseshoe Curve which is a railroading historic landmark.

http://www.railroadcity.com/visit/world-famous-horseshoe-curve/

Ann, you have many options, depending upon how much time you have and your interests.

E.g., you could head north on I-79 to Grove City Premium Outlets, a shopping mecca for multi-state region and for southern Ontario as PA has no sales tax on clothing or footwear.

You might more enjoy heading east on I-80 to Ricketts Glenn State Park. See the discussion here:

http://www.tripadvisor.com/ShowTopic-g1-i12567-k7526745-Less_crowded_alternatives_to_most_famed_NPs-Road_Trips.html

From Ricketts Glen, you could head north on a state road to I-86 visiting the great waterfalls of the Ithaca area. Check out Taughannock Falls, I belief the tallest in the East at over 200 feet freefall, and Robert H. Treman State Park, which has a natural swimming pool nestled under a waterfall. Ithaca also has a great farmers market on weekends at Steamboat Landing.

http://www.gowaterfalling.com/waterfalls/taughannock.shtml

http://nysparks.com/parks/135/details.aspx

You then could visit Saratoga Springs, NY, site of one of the most consequential battles in world history, or drive through the Berkshires on your way to Boston.

Good planning!

There are even more options in the Philadelphia area and NJ.

Thanks again, everyone!

You would have canoeing options in the Ithaca area as well. Cornell University, one of the Ivies, is located in Ithaca, and has one of the most beautiful locations of any U.S. university.

Saratoga Springs is an old resort town, especially popular among the rich in the Gilded Age. The potato chip was invented here.

http://www.nps.gov/sara/index.htm

http://en.wikipedia.org/wiki/Saratoga_National_Historical_Park

This topic has been closed to new posts due to inactivity.

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Home » North America » USA » New England

EPIC New England Road Trip Itineraries (2024)

Going on a New England road trip  has to be one of the best ways to experience the region! With your own vehicle, you’ll be able to go wherever you want, stay where you like, and see whatever you fancy.

New England has been charming visitors for a long time. Of all of the regions in the USA, New England has some the richest history (being the birthplace of the nation and all), some of the most exciting locals, and best seafood, period.

And the fall foliage in New England? What more can be said about this phenomenon that hasn’t be said by dozens of movies – it’s simply one of the most romantic sights in the USA.

New England is by no means cheap nor easy to travel without some guidance. In order to see the best of New England, and not drop a fortune while doing so, you’re going to need a little assistance.

Don’t worry – we have the insider information you need for an EPIC journey. So what are we waiting for?! Let’s get the ball rolling on your New England road trip itinerary!

Best Time of Year to Road Trip New England

Best new england road trip itineraries, places to visit in new england, off the beaten path new england road trip ideas, new england road trips costs, final thoughts about new england road trips.

With something always going on, a road trip to New England is possible at any time of the year! In New England, summers are for beach trips, fall is for the foliage, winter is for skiing, and spring is for festivals.

If you can stand the occasional poor weather – the blinding snow and sometimes uncomfortable humidity – then you’ll do just fine in New England.

The climate in New England isn’t always agreeable, a fact that many residents will remind you of when you’re there. Winters are long and can be bitter cold and summers feel unfairly humid and short.

The Broke Backpacker is supported by you . Clicking through our links may earn us a small affiliate commission, and that's what allows us to keep producing free content 🙂 Learn more .

The weather in New England has a habit of being bipolar as well, appearing beautiful one moment only to turn to shit in a moment.

This doesn’t stop New Englanders from having a good time though as they seem to have something to do 365 days of the year. They take the weather with a grain of salt, as they should, and simply say, “if the weather’s no good, just wait 15 minutes (and it’ll be better).”

Outside of the mountainous regions, which can have Arctic qualities, there are no huge climatic swings in New England. Overall, temperatures are relatively cool and precipitation is spread throughout the year.

What makes New England feel so cold is the Canadian winds that come down and wreak havoc. These winds penetrate to the bone and can really ruin your day.

A thermometer may read 30 Fahrenheit but with the wind chill, it could feel like 0. Be sure to bring lots of layers and a windbreaker in the winter.

Fall in New England means changing foliage, the astounding beauty of which attracts every Joe Schmoe and his family to visit. If you’re on a road trip during this time, expect much higher prices and much less availability. Having said that, it’s one of the best places in the world to visit in September and October, so it’s worth it!

Get 15% OFF when you book through our link — and support the site you love so dearly 😉

Booking.com is quickly becoming our go-to for accommodation. From cheap hostels to stylish homestays and nice hotels, they’ve got it all!

Below is a list of sample New England road trip routes, from East Coast budget adventures to more comprehensive trips that cost a bit more. Varying from 4 to 14 days in length, they cover many of the top destinations in New England. Each itinerary provides day-by-day highlights, which are meant to give you some good New England road trip ideas.

The USA is  blisteringly beautiful. It’s also blisteringly expensive! Visiting two national parks in day can run you $70+ in entry fees.

Orrrr… you kick those entry fees to the curb, buy an annual ‘America the Beautiful Pass’ for $79.99,  and get unlimited access to ALL 2000+ federally managed sites in the States totally FREE!

You do the math. 😉

4-Day New England Road Trip Itinerary: Boston and the Cape

4 Days: Boston and the Cape

Arrive in Boston via Logan International Airport or by other means. Once you’re checked into your lodge and settled in, get ready to see the town!

Our  Boston itinerary  includes a visit to downtown Boston to see:

• Fenway Park
• The Freedom Trail
• Acorn Street
• Trinity Church
• Boston Commons

After that, head to bed because the next day we start again!

Today you’ll be getting off the beaten path in Boston.

• Southend for an authentic Bostonian experience
• Cambridge for Harvard and MIT
• East Boston for good food and views
• Walden Pond for transcendental fans
• Bunker Hill for history

Today we’re officially starting the drive, so have your car organized for a road trip to Cape Cod. Start driving on Highway 6 and then transfer to Highway 3 prior to the Cape Cod Canal. Once you’ve arrived, find your Cape Cod lodge/campsite and get set up.

Next, we’ll explore the Cape. Activities include:

• Lighthouses
• Charming settlements
• Trinket shopping
• Historical landmarks
• Biking and hiking
• Cape Cod Rail Trail

This is the last day of your short road trip from Boston. You can opt for a few different choices today.

Either consider visiting Nantucket Island or Martha’s Vineyard via the ferry. If not though, you can continue exploring the island and seeing what’s around.

When all is said and done, pack your things for a late flight in the evening or a flight the next day.

7 Day New England Road Trip Itinerary: New England’s Best Fall Foliage

7 Days: New England’s Best Fall Foliage

• Arrive at Logan International and organize your car; skip this if you’re coming by road from elsewhere.
• Hit the road immediately and head west on the I-90 and I-84 for Hartford, CT.
• Pass Hartford and continue onto the Litchfield Hills in West Connecticut.
• Spend the night in Kent, Cromwell or elsewhere.
• Admire the foliage.
• Depart from your lodge and head north on I-7 through the Housatonic Valley; red and gold foliage in abundance.
• Arrive at the junction between I-7 and Highway 2 near Williamstown.
• Highway 2 is colloquially referred to the Mohawk Trail, which offers some of the best of New England as well as excellent fall colors.
• Stay nearby and drive along the 2 to your heart’s desire.
• Drive on the Mohawk Trail if you haven’t already.
• When ready, head for Green Mountain National Forest of Vermont via I-7 again.
• Drive through the Green Mountains until Burlington.
• Grab a beer and chill for the night.

Today is a long but rewarding day.

• Depart from Burlington and head for Cambridge, VT.
• Hit the 108 and Smuggler’s Notch for excellent mountain views and foliage.
• Make your way east towards Bath, New Hampshire.
• Turn onto Highway 112 before Bath, which is the beginning of the Kancamagus Highway.
• Continue onto Lincoln, admiring the scenery along the way.
• Find a Lincoln Airbnb or stay in North Conway or elsewhere in the White Mountains.
• Finish the Kancamagus Highway (112), which terminates at Conway.
• Head north upon reaching Conway on Highway 16.
• Enjoy Mt Washington and White Mountain National Forest, which is particularly fantastic in fall.
• Turn onto I-2 and then again onto 113 to reach Evans Notch.
• Finish up and head south towards Portland for the night.
• Drive to Acadia National Park , which is one of the best places for fall foliage in New England.
• Make a tour around Mt Desert Island and get a full dose of autumn splendor and coastline.
• Spend the night around Acadia or back in Portland.
• Consider spending the night in Camden as there is excellent foliage here.
• Pack up and head back to Boston.
• Spend the day exploring the city.
• Get ready to depart that evening or the next day.

14-Day New England Road Trip Itinerary: Ultimate New England

14 Days: Ultimate New England Road Trip

Follow the first East Coast itinerary listed here  except  instead of returning to Boston at the end of day 4, relax and stay the night in Cape Cod. We’ll be moving on from there the next day…

• Depart from Cape Cod and hit I-6, which will take you all the way to Providence, Rhode Island.
• Explore the city and its architecture.
• Be sure to drop by one of the many breweries and brewpubs.
• Spend the night in or around Providence.
• Wake up and head directly for Newport via Highway 114.
• Spend the day exploring the opulent town.
• Be sure to visit the many mansions and estates as well as Fort Adams in the south.
• Depart when you’re ready.
• Drop by Narragansett for some beach time if you have time.
• Stop in Old Saybrook for the night or continue onto New Haven.
• Depart from your lodge and make your way north.
• Head to the state capital Hartford.
• Wadsworth Falls
• Buttermilk Falls
• Settle in Hartford for some culture and good partying or…
• Head to Litchfield Hills for a quieter night.
• Make your way up Knowledge Corridor or Housatonic Valley towards Vermont.
• Be sure to drop by the Mohawk Trail in Northwest Massachusetts for some scenery and history.
• Hit highway 7 and make the long drive to Burlington.
• Reward your hard work today with a beer.
• Spend the day exploring the Green Mountains of Vermont.
• Climbing the  Camel’s Hump .
• Hiking around  Mt Mansfield .
• Check out  Smuggler’s Notch .
• Rafting on the  Mad River .
• Spend the night in Burlington again.
• Depart from Burlington and head east towards Lincoln, New Hampshire via I-89.
• Arrive in the White Mountains and settle into whatever lodge/campground you have booked.
• Spend the remainder of the day in the mountains.
• Flume Gorge
• Mt Washington
• Franconia Notch
• Arethusa Falls
• Lonesome Lake
• If you arrived early enough, considering overnighting in a backcountry campsite.
• Wake up and knock off any remaining activities.
• Consider doing the full-day Presidential Traverse but, full-warning, it’s quite arduous.
• Lay your head down for the night, preferably around a campfire with a drink.
• Depart from the White Mountains and travel on Highway 302 to Portland, Maine.
• If you stay in Portland, visit the many maritime landmarks, trinket shops, and breweries.
• Spend the day exploring Acadia National Park.
• Taking a road trip around  Mt Desert Island .
• Climbing  Cadillac Mountain .
• Visiting  Jordan Pond .
• Relaxing on  Sand Beach .
• Walking around  Bar Harbor .
• Head to your lodge for the night.

Below is a list of the best road trip destinations in New England. Study them well and decide which ones you like the most.

Road Trip to Boston

Boston is the largest city in New England and, honestly, one of the coolest cities in the entire United States. With gorgeous architecture, some of America’s most important history, and hugely diverse demographics, there’s little chance you’ll run out of things to do in Boston .

Downtown Boston – the area with all the skyscrapers – is where you’ll find the majority of the city’s attractions. Notable points of interest in Boston Downtown include Fenway Park , the Trinity Church, Boston Commons, Acorn Hill , and the North End. You could easily hit all of these places in a few hours by walking.

North across the Charles River is Cambridge , home to the famously exclusive Harvard College and MIT . Both campuses are worth visiting – the former for traditional architecture and the latter for ultra-modern. The whole of Cambridge is pretty affluent, being inhabited by students and leaders in tech, but thankfully doesn’t suffer from too much snootiness.

South Boston is the home of the “southies” aka those people that sound like Matt Damon from Good Will Hunting . Aside from the impressive JFK Library, there isn’t a whole lot to do here besides people watch, which is, admittedly, awesome.

Finally, across the Boston Channel and next to Logan International is East Boston, which is where most of the immigrants live. These means this is one of the best places in Boston to grab food! The views ain’t bad either.

While you’re travelling around Boston , be sure to also get outside of the city of as well! The historical city of Concord , as well as the hallowed Walden Pond , are both worth a day trip.

Road Trip to Cape Cod and the Islands

Cape Cod is a large, prominent peninsula located south of Boston. It is an immensely popular getaway destination due in part to its extensive coastline and profuseness of quaint coastal towns.

Combined with the ever-enchanting Martha’s Vineyard and Nantucket Island , both located nearby, and you have an assembly of some of the best of New England.

Cape Cod is a very large region, surprisingly so, and is broken into several districts. Because of its size, history, and prosperity, Cape Codians are very proud of their home and consider it more than just a tourist destination. There are loads of great places to stay in Cape Cod , if you fancy extending your trip!

There are several charming towns on Cape Cod that are worth visiting. Hyannis is most notable for the Kennedy Compound , which served as the holiday home for JFK and his family, as well the enormous Beech Tree on Main Street .

Fans of Kurt Vonnegut may also be interested in nearby Barnstable as it was his home for several decades. Affluent Chatham has one of the best lighthouses and local baseball teams on the Cape (Cape Codians are crazy for the sport).

Finally, Provincetown is famous for its artsy and expressive LGBT community.

Most everyone comes to Cape Cod to play in the sea as the peninsula has some of the best beaches in New England. Make no mistake, there are a lot of them too.

Stunning stretches of sand can be found at Nauset Beach, Lighthouse Beach, Sandy Neck Beach, Mayflower Beach, and pretty anywhere else along the Cape Cod National Shoreline Park . You may get lucky and even see a migrating humpback whale!

No road trip to Cape Cod is complete without a trip to Nantucket Island or Martha’s Vineyard – both are among the most desirable places to visit in New England, during summer especially so.

Martha’s Vineyard is full of grand residences for the rich as well as picturesque beaches. Nantucket is similar to Martha’s Vineyard but smaller and quieter. You can catch a ferry to either at Hyannis.

Road Trip to Rhode Island

Rhode Island has a little bit of everything. The largest city, Providence , is often considered a good alternative to Boston, and the surrounding state offers quintessential scenery including rugged coastline, quaint townships, and, of course, the fall foliage New England is so beloved for.

Providence is the third largest city in New England. For a long time, Providence had a bad reputation for being sketchy, crime-ridden, and corrupt but, following massive economic pushes, is currently undergoing an urban renaissance. It’s now a very appealing city thanks to its history with a bustling college scene, solid nightlife, and heaps of stuff to do .

Providence is a small city so getting around on a foot is a very reasonable task. Walk around and take note of the diverse architecture. Be sure to see the State House, the eclectic Brown University, the restored Arcade, and the First Baptist Church , among others, for a lesson in American architectural history.

For a languid afternoon, try visiting one of the many museums and/or parks in Providence. Certain neighborhoods, like Federal Hill, College Hill, and Downcity all offer nice urban panoramas as well. End your day at one of the many breweries in the city.

Rhode Island’s other noteworthy city is Newport . An opulent town, full of mansions and elegant avenues, Newport is a prime example of New England decadence. Rosecliff estate served as a setting in the recent Great Gatsby film and its neighbors – The Beakers and Marble House – are equally grandiose.

There is a thriving art scene in Newport and jazz, in particular, is praised here. There is an awesome jazz festival at Fort Adams. Festival or not, Fort Adams is worth seeing because it is one of the most important historical structures in New England.

Newport has many beautiful city beaches including Bailey’s, Easton, and Gooseberry. To see some real contenders for “best beaches in New England,” head across the Jamestown Verrazano Bridge to Narragansett . If you’re ever wondering where to stay in Newport, you should definitely consider staying in one of the more historic bed and breakfasts in Rhode Island there.

Coastal Connecticut Road Trip

Connecticut is an eclectic state visited often by both New Englanders and New Yorkers, the latter of which only live a short train ride away. It is a popular getaway for city folk who need a break from the grind and some time in rural New England.

With a lovely coastline, romantic countryside, and a number of dynamic cities, Connecticut is a great stop along any New England road trip route USA.

Connecticut can be broken down roughly into three parts: the coast, the “Knowledge Corridor,” and the countryside. This section will cover coastal Connecticut , which is a part of Southern New England.

Driving west along Highway 95 from Rhode Island, you’ll pass by some of the most beautiful beach towns in New England. Stonington is a good place to learn about the maritime history of the state – particularly at the Old Lighthouse Museum .

Old Saybrook is one of the prettiest coastal towns in Connecticut and is also a stone’s throw away from Gillette Castle . On the way to New Haven is Hammonasset Beach , which is the longest and busiest beach in the state. Make sure to stay in one of the stunning cabins in Connecticut to make the most out of all this natural scenery.

New Haven marks the beginning of a long stretch of urban development that spans all the way to New York state.

New Haven is most famous for Yale University , which is arguably the top attraction in the city. Being a college town, New Haven has a great art scene and nightlife. The pizza is also particularly good in this town.

As we continue further west along 95, we’ll pass by many more beautiful New England towns. There’s quiet Milford , which has a great beach called Silver Sands .

Next, you’ll pass through industrial Bridgeport . After that is upscale Stamford , glorified dockyard for millionaires from New York (there are some good beaches as well).

Finally, you’ll end up in Greenwich , which is one of the most admired towns in New England, due in part to its beauty and close proximity to New York.

There are a ton of awesome B&Bs in Connecticut where you can stay in a historical building and enjoy that welcoming East Coast hospitality.

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Road Trip through Connecticut and Massachusetts

The interior of Connecticut is dominated by the Knowledge Corridor , which hosts one of the densest collections of higher learning institutions, not to mention one of the largest populations in New England.

Travel outside this packed area and you’ll find some of some of the best of New England pastoralism including traditional townships, rolling hills, and a distinctive tranquility. Visiting either on a New England road trip provides excellent insight into the region.

Let’s start with the quieter section – the western part of Connecticut referred to as the Litchfield Hills. This part of the state is very rural with few inhabitants and even fewer visitors.

There are a number of beautiful New England towns here, including Kent , Cornwall , and New Milford , as well some lovely natural attractions like Kent Falls, Burr Pond, Candlewood Lake, and Mohawk Mountain . These are also some of the best places to visit in New England in the fall.

Moving along to our main destination, we first make for Hartford , Connecticut’s state capital and the beginning of the Knowledge Corridor. Hartford is considered one of the great culture capitals of the region.

There are several libraries and art collections dedicated to various historical figures, including Mark Twain, spread throughout the city. Reportedly, West Hartford also has a fairly active nightlife.

Outside of Hartford are a number of parks worth visiting. Examples include Enders State Forest/Falls, Buttermilk Falls , and Wadsworth Falls .

We continue our New England road trip north on Highway 91 through the Connecticut River Valley. This is the heart of the Knowledge Corridor, a title that refers to the huge concentration of colleges and universities in the area. This corridor runs all the way into Massachusetts and terminates in Springfield.

Springfield is a great city full of Victorian architecture and some of the coolest museums in New England. Be sure to visit the NBA Hall of Fame , if you’re interested in sports, as well as the Dr. Seuss Sculpture Museum , if you had a childhood.

Vermont Road Trip

True to its nickname, Vermont aka The Green Mountain State is a wild wonderland and a favorite playground for New England outdoors people. With some awesome skiing and hiking in addition to several fall foliage drives, which are among the best in New England, Vermont is a great escape from the more developed CT, MA, and RI. Here is the best opportunity to stay in a cabin in Vermont for a truly off-the-grid experience.

Starting in the south of Vermont, you’ll first arrive at the mountains from which the state gets its name, the Green Mountains . A subrange of the Appalachia, the Green Mountains are home to the state’s highest peaks as well as the best mountain activities.

Some of the best ski resorts in Vermont are Sugarbush, Stowe Mountain, Killington, Mount Snow , and Jay Peak. Though the slopes aren’t as epic as say those in Colorado or Oregon, they still get dumped on with snow and have decent runs.

If skiing isn’t your bag, why not try portions of the Green Mountain Long Trail ? This extension of the Appalachian Trail is noteworthy for hitting all the range’s highest peaks but is, for this reason, difficult at times.

Casual hikers and campers can also take advantage of the many free backcountry campsites and quaint bed and breakfasts in Vermont .

Other natural attractions worth visiting in Vermont are the Mad River, Quechee Gorge, Camel’s Hump , and the many gorgeous lakes – most notably Lake Willoughby and Lake Champlain.

Montpellier is the state capital of Vermont though Burlington is the largest and most exciting in the state.

Burlington is famous for being a hippy town as well as drop dead gorgeous because it lies on the banks of Lake Champlain. Burlington makes for an excellent base for exploring Vermont’s outdoor spaces with many quality bike paths for cycling enthusiasts.

Like any good liberal college town, Burlington has plenty of bars, and the breweries, in particular, are excellent. You ca check out Airbnbs in Vermont for cozy and comfortable stays.

Road Trip to New Hampshire

New Hampshire is very similar to Vermont in that it’s mostly visited for its epic settings and free-spirited culture. With the highest peak in all of New England, Mount Washington , as well as the beautiful White Mountains , New Hampshire is another great New England road trip destination for adventurous travelers.

If you’re on a summer New England road trip, then you’ll obviously want to hit the trails in New Hampshire. This state has some of the best hikes in New England in addition to some decent summits.

As previously mentioned, Mt Washington is the highest peak in New England and can be summitted in a day either by foot or by cog train (that’s cheating though). Be mindful of foul weather.

New Hampshire’s Mt Monadnock is argued to be the second most climbed peak in the world next to Mt Fuji, but many don’t count Monadnock because it has no glacier. (Mt Hood in Oregon is the second most climbed glaciated peak in the world.)

Another rewarding and arduous hike is the Presidential Traverse where you navigate across 11 of the state’s highest peaks. Also consider visiting Lake Winnipesaukee , Franconia Notch, Arethusa Falls, Lonesome Lake , and the Flume Gorge .

Those on a winter or spring New England road trip will be happy to hear the skiing is also quite good in New Hampshire. Popular ski resorts include Loon Mountain, Bretton Woods, Cannon Mountain , and Waterville Valley .

New Hampshire is pretty sparsely populated and there aren’t too many bustling urban centers here. There are a couple of little towns worth stopping in still.

Hanover is home to the famous Dartmouth University and is gorgeous in its own right. Jackson is a gorgeous place to stay in the White Mountains and makes for a great base. Finally, Portsmouth is one of the most historically significant towns in New England and, more importantly, has great breweries.

Road Trip on the Maine Coast

Maine will be a highlight for any New England Coast road trip! With epic seascapes and even more epic seafood, Maine has a lot to offer.

Many people have fallen in love with Maine’s coastline, too many perhaps. Coastal Maine isn’t exactly hidden these days and so anyone on a summer road trip in New England will have to deal with large crowds.

You can definitely get off the beaten path in Maine but that is a topic that we will be discussing in the next section .

Driving from Portsmouth, NH, you’ll head north on the 95 to Portland , Maine, catching glimpses of the shoreline along the way. You’ll pass by several of Maine’s best beaches and towns including York, Ogunquit, Cape Elizabeth , and Goose Rocks . Upon arriving in Portland, you may think that it’s a small coastal town but is, in fact, the largest “city” in the state.

Portland is one of the best places in New England, ridiculously charming and full of quaint little attractions. You’ll learn a lot about its maritime history at the Old Port and also be afforded the opportunity to shop for artisanal souvenirs. The seafood is obviously excellent in Portland and the beer is especially delicious if not abundant.

Moving on from Portland, we continue our New England coast road trip deeper into the state. Driving on the 1 you’ll have lots of opportunities to visit the coast. Boothbay is an elegant destination, Camden is gorgeous, and Popham Beach is arguably one of the best beaches in New England.

Our ultimate destination is Acadia National Park , the only national park in New England. It is a superlative place with some astounding scenery, not to mention some of the best hikes in New England.

Spend the night in the charming seaside town of Bar Harbour , where you’ll get to try Maine’s famous cold lobster roll. You’ll find some epic Maine B&Bs here run by friendly locals.

Then go for a drive around Mt Desert Island , the island on which Acadia is located, and then explore local sites like Jordan Pond and Sand Beach . Note that you’ll have to pay an entry fee for Acadia.

Below is an overview of the Great North Woods of New England, arguably the wildest place in the Northeast. Those with the will and proper transport will be rewarded with virgin woods, pristine rivers, and an abundance of local wildlife.

Great North Woods

The Great North Woods is one of the quietest, most underdeveloped, and most beautiful places in New England. It refers to the extremely wild and untouched woodlands of northern New Hampshire, Vermont, and Maine that separate New England from Canada.

With little, if any tourist infrastructure, the Great North Woods should be an awesome adventure for anyone looking for a proper USA backcountry experience on their New England road trip.

There are a fair bit of activities in the New Hampshire part of the Great North Woods. Many of New England’s best waterfalls are in this region including the spectacular Beaver Brook Falls . There’s a very complex and thorough network of trails here as well that penetrates deep into the woods.

You can drive to Great North Woods in Maine from New Hampshire via Highway 16 and pass some excellent scenery along the way. This area is one of the best places to visit in New England in the fall because of the spectacular foliage. Be careful of moose though! These giants will run into the road sometimes and seriously ruin your car.

Maine’s North Woods is expansive and is probably the most remote part of New England. It is, in fact, so out-there that certain counties like Aroostook are not even officially incorporated into the state and so have no “official populations.”

Stories of the wood’s frightful and fantastic inhabitants still circulate to this day as well, like that of the vengeful wendigo or of the murderous ding-balls.

Interior locations like Baxter State Park and Mt Katahdin are the most “accessible” places in Maine’s North Woods. Surrounding these is 100 Mile Wilderness , which is often visited by ACT hikers. If you want to travel further than these locations you may need a 4×4 as paved roads are no longer guaranteed.

If you can make it, the Allagash Wilderness is one of the great river adventures in America. Navigable only by canoe or raft, there is nothing out here besides moose, fish, and untouched landscapes.

A road trip through New England ain’t going to be cheap, folks. With the high costs of living and high demand, New England has some of the steepest hotel rates and dining prices in the USA.

That’s no reason not to visit New England in the first place though! You have us, after all. 🙂

We at The Broke Backpacker are constantly looking for new ways to save on travel and have a whole repertoire of useful tips to share with y’all. Even if we are unable to travel for $10/day like in our favorite countries (let’s be real here), we can at least help you minimize expenses to the utmost degree.

The average daily budget for a New England road trip is between $200-$250 – this includes gas, a rental car, lodging, food, drink, and entry fees.

On any road trip, New England or otherwise, the largest cost will be gas . This expense will always sneak up on you because it can be difficult to properly gauge how much you will actually use.

Lodging is also expensive in New England. Try and camp out as much as possible to lower your daily budget significantly. Take advantage of the cheaper public campsites and occasional backcountry site, which are sometimes free. Stay in hostels as well – they’re not so bad in New England.

Food costs are something you can control as you will have the option of cooking cheaply at home or the campsite. Dining is expensive in New England so be picky about how many lobsters you eat and clam bakes you attend.

Below is a breakdown of the average costs of a road trip in New England.

Average Costs of a New England Road Trip

Rental car : $50-$150

RV rental :  $100-$300

Gallon of gas:  $2.74

Private AirBnB home:  $140

Hotel room:  $150

Hostel:  $25-$35

Campground:  $10-30 (sometimes free!)

Sandwich:  $6-$9

Beer at a bar:  $5-$8

Coffee:  $3-$4

Bottle of Whiskey from the market:  $25

Dinner for two:  $35-$60

Best Places to Stay in New England on a Budget

Camping in new england.

Camping in New England is either done on public land, private land or in the backcountry . Each type offers different sorts of amenities and at different prices.

Private campgrounds usually have more amenities and can accommodate more types of campers. RV parks, hookup sites, and other sorts of demanding camping (we hesitate to use the word “glamping”) are usually found at private camps.

Private camps usually have lots of communal facilities like a kitchen and showers. Because of their greater comfort, private campgrounds are usually more expensive.

Camping on public land, run either by the state or the feds, is usually more basic. Electricity is possible as is the occasional shower but don’t expect the resort-like services that private campgrounds have. Fortunately, prices are far more reasonable at public campgrounds.

Both public and private campsites fill up quickly in the fall. Many take reservations though and we suggest you do this if you’re going on a fall foliage road trip in New England.

Backcountry campsites, being located on either private or public land, are harder to access but have the benefit of being extremely cheap if not totally free . These campgrounds usually require a hike or maybe a water taxi to reach, which makes them difficult and unattractive for the average camper.

The backcountry campgrounds are also very primitive, often with no restrooms and maybe running water. For the intrepid, these campgrounds can be very ideal as they’re super quiet, wild, and, as previously mentioned, usually free!

Backcountry campsites are usually found in the mountains, around the lakes, and on the remote islands of New England. Use this search engine for a compendium of free camping in New England .

Always have of plenty of powerful bug spray and mosquito repellent on you. Mosquitoes are a plague in the summer. Be sure to also wear long clothing to protect yourself from ticks when hiking in the backcountry. Local ticks often carry Lyme Disease, which is an autoimmune disorder with no cure.

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Renting a Car or Campervan in New England

Renting a car is the most popular way of getting around New England. There are a myriad of car rental agencies here that offer varying deals and varying models.

To find the best rental car deal in the USA, use search engines that compare the prices from individual companies. We personally like using rentalcars.com as they’ve never failed to give us a great price.

You can also rent and travel in a campervan , which means you don’t have to worry about packing camping gear. You will have to empty and refill the various wascampete and water tanks though, which will require a visit to the proper facilities. RVs also cost more to rent, use more gas, and demand higher prices at campgrounds. We suggest booking a campervan with Outdoorsy as they usually have a good selection and good prices.

Make sure you also purchase a RentalCover.com policy to cover your vehicle against any common damages such as tires, windscreens, theft, and more at a fraction of the price you would pay at the rental desk.

The roads in the Northeast are generally very good and a sedan or economy car should deliver you to most of New England’s top destinations. Only in the most remote portions of the Great North Woods, will the roads be so bad that you need 4×4 or at least high clearance.

If you’re on a road trip in New England during the winter and want to go to the mountains, you will definitely need all-wheel or 4-wheel drive.

Getting Insured for a Road Trip through New England

Concerned about staying safe in the USA? Well don’t be! Just make sure you’re insured, and you drive carefully.

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

New England is no doubt one of the most idyllic regions of the US. Quaint coastal towns and some of the best foliage in the country are but two reasons to take a road trip here–but there are so many more.

Hopefully, you now feel more prepared on where to go and what to do on YOUR New England road trip.

But rest assured that regardless of which spots you’re bound to find beauty, history and a whole lot of delicious seafood.

So what are you waiting for? The open, rural roads of New England awaits!

Updated February 2023 by Samantha Shea

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Wow! great article and suggestions.

thank you for all of the advinces it helps, can t wait to visit New England Vermont Maine, xxx

Lake placid in the Adirondack Mountains also a try while stop. There are several private and New York State campgrounds nearby.

Thank you for mapping this all out. I live in New England and would love to visit many of these places.

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Cost to drive from Pittsburgh to Boston

 total cost = $82.80.

 Travel distance from Pittsburgh, PA to Boston, MA

 Travel time from Pittsburgh, PA to Boston, MA

 Pittsburgh, Pennsylvania

How much does it cost to drive to Pittsburgh, PA from here?

 Boston, Massachusetts

What's the cost of driving to Boston, MA from where I am now?

Calculate the driving distance and total travel time from Pittsburgh to Boston by car if you're planning a road trip. Get driving directions from Pittsburgh, PA to Boston, MA . Compare the flight distance to driving distance from Pittsburgh, PA to Boston, MA . Or find out if it's better to fly or drive from Pittsburgh, PA to Boston, MA ?

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Pittsburgh to Boston via New York City

Pittsburgh to boston road trip planner.

Here's a sample itinerary for a drive from Pittsburgh to Boston. If you're planning a road trip to Boston, you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops . Camping along the way? Search for RV campgrounds . Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.

10:00 am  start in Pittsburgh drive for about 1 hour

11:10 am   Fallingwater stay for about 1 hour and leave at 12:10 pm drive for about 1.5 hours

1:36 pm   Breezewood stay for about 1 hour and leave at 2:36 pm drive for about 1.5 hours

4:12 pm   Harrisburg stay for about 1 hour and leave at 5:12 pm drive for about 1 hour

day 1 driving ≈ 5.5 hours find more stops

9:00 am  leave from Reading (Pennsylvania) drive for about 2.5 hours

11:22 am   New York City eat at Katz's Delicatessen stay for about 4 hours and leave at 3:22 pm drive for about 2.5 hours

5:54 pm   Springfield (Massachusetts) stay for about 1 hour and leave at 6:54 pm drive for about 1.5 hours

8:33 pm  arrive in Boston stay at The Westin Copley Place

day 2 driving ≈ 6.5 hours find more stops

Where should I stop along the way?

Fallingwater   (7 mentions) Breezewood   (3 answers) Harrisburg   (25 answers)     questions about Harrisburg:         What are the 5 best sights to see in Harrisburg PA Reading (Pennsylvania)   (4 answers) New York City   (648 answers)     Central Park   (149 mentions)     High Line Park   (110 mentions)     The Metropolitan Museum of Art   (85 mentions)     Statue of Liberty   (69 mentions)     Times Square   (59 mentions)     restaurants around New York City:         Katz's Delicatessen         Shake Shack         Lombardi's Pizza         Balthazar Restaurant         Eataly     questions about New York City:         Is it a good idea to visit NYC in December?         free or cheap things to do in NYC         What is your favorite restaurant in New York City?         48 Hours in NYC - I NEED to know the best Pizza spots!         Which NYC museums are must see? We only have time for two. Springfield (Massachusetts)   (5 answers)     questions about Springfield (Massachusetts):         Best free things to do in Springfield (Massachusetts)?

Where's the best place to stay in Boston?

Are you going straight to a hotel, or looking for a vacation rental or Airbnb?

The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Boston .

You can also see most people recommend as the best amount of time to visit. Find out how many days in Boston to stay.

If you're looking for a quick answer, you can check out The Westin Copley Place , which was mentioned 4 times on Trippy.

Here are some more hotels people talk about:

Want to research more popular hotels in Boston? Click the blue button below.

Where's the best place to eat in Boston?

Need some recommendations on somewhere to get food?

Trippy members suggest Mike's Pastry , which was mentioned 15 times.

Here are some more restaurants people talk about:

Want to research more popular restaurants in Boston? Click the blue button below.

What are some things to do in Boston?

This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.

These are some of the places people talk about on Trippy:

Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!

For example, here are some questions people have asked about Boston. Click on any question to see answers from the community!

Click the button below to explore more questions and answers related to Boston.

Do I really have to go back home?

Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!

Want to plan the trip back? Get the reverse directions for a Boston to Pittsburgh drive , or go to the main page to plan a new road trip .

You can also compare the travel time if you're flying or driving by calculating the distance from Pittsburgh to Boston . Or get a full Pittsburgh to Boston flight plan .

Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.

And if you know Pittsburgh well, please help your fellow travelers and answer their questions about Pittsburgh!

More info on this route:

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Best Road Trips From Pittsburgh

Top road trip destinations from pittsburgh.

Pittsburgh to Niagara Falls

🚗 240 miles ⏱️ 3 hours, 50 minutes

Explore the stunning beauty of Niagara Falls on a quick drive from Pittsburgh. One of the most well-known waterfalls in the entire world and the oldest state park in New York, Niagara Falls is a bucket-list destination that lives up to the hype.

Make sure to visit Prospect Point Observation Tower , which offers a great lookout over all three major falls.

Pittsburgh to Seven Springs Mountain Resort and Laurel Hill State Park

🚗 60 miles ⏱️ 1 hour, 10 minutes

Enjoy a quick getaway from Pittsburgh to Seven Springs Mountain Resort, perfect for skiing, hiking, and enjoying the great outdoors. A favorite location for family vacations.

Stop by The Laurel Hill State Park, the result of a huge continuing conservation effort, and fantastic for birdwatching, fishing, boating, and swimming.

Pittsburgh to Finger Lakes and Ithaca

🚗 300 miles ⏱️ 5 hours, 50 minutes

Drive from Pittsburgh to the scenic Finger Lakes and Ithaca, an area known for its wineries and stunning natural landscapes. The streams that flow north here create spectacular waterfalls and various Underground Railroad escape routes are compelling.

Make sure to check out Cherry Springs State Park as you make your way to the Finger Lakes.

Pittsburgh to Knoxville and Great Smoky Mountains National Park

🚗 490 miles ⏱️ 7 hours, 40 minutes

Embark on a journey from Pittsburgh to Knoxville and the Great Smoky Mountains National Park. People are drawn to Knoxville for its liveliness and beauty, along with its football culture and savory Southern food.

Fall and spring seasons are when the colors of surrounding Great Smoky Mountains National Park really come to life.

Pittsburgh to New York

🚗 410 miles ⏱️ 6 hours, 50 minutes

Travel from Pittsburgh to New York City via Philadelphia, and you are in for a treat, with the journey packed with vibrancy, historical sites, and excitement across two of America's most iconic cities.

Along the way also make interesting stops at Donegal , Tuscarora State Forest , and Harrisburg , the state capital of Pennsylvania.

Pittsburgh to Happy Valley and Rothrock State Forest

🚗 140 miles ⏱️ 2 hours, 30 minutes

Journey from Pittsburgh to Happy Valley and explore the natural beauty of Rothrock State Forest, a haven for hiking, mountain biking, and wildlife viewing.

Driving South you'll pass Monroeville and Allegheny Township , before first arriving at Rothrock State Forest , ahead of Happy Valley.

Pittsburgh to Baltimore

🚗 250 miles ⏱️ 4 hours, 50 minutes

Travel from Pittsburgh to Baltimore and discover the rich history and vibrant harbor life of this bustling city. The Inner Harbor of Baltimore houses attractions for all ages, including museums, restaurants, and most notably, moored historic ships.

Highlights on this trip include stops at Michaux State Forest and Gettysburgh .

Pittsburgh to Philadelphia

🚗 310 miles ⏱️ 5 hours, 10 minutes

Drive from Pittsburgh to Philadelphia and it is a trip bursting with rich American history and culture of the City of Brotherly Love.. With landmarks including Independence Hall and the Liberty Bell you won't be short on things to see and do.

Make sure to stop at Harrisburg . The Pennsylvania State Capitol Complex is among the nation's most impressive state capitols.

Pittsburgh to Luray and Shenandoah National Park

🚗 250 miles ⏱️ 4 hours, 30 minutes

Explore the stunning landscapes of Shenandoah National Park. The thundering waterfalls and granite mountains have long of this forest have long been a retreat for Presidents and people of power because of their closeness to Washington DC.

Here you can hike the famously scenic Appalachian Trail using Luray as your base.

Pittsburgh to Washington, DC

🚗 250 miles ⏱️ 4 hours, 20 minutes

Take a trip from Pittsburgh to Washington, DC, and visit the nation's capital to explore its monuments, museums, and the political heart of the United States.

Stop off in Historic Downtown Frederick , a well-preserved section of the city that has more than 200 museums, art galleries, specialty shops and restaurants.

Pittsburgh to Chautauqua Lake and Jamestown

🚗 160 miles ⏱️ 2 hours, 30 minutes

Head from Pittsburgh to Chautauqua Lake and Jamestown for a refreshing lakeside retreat, with the lake deservingly famous for its sailing and fishing offerings.

You can choose to detours past Allegheny National Forest to enjoy the splendor of Pennsylvania's only natural forest.

Pittsburgh to Erie and Lake Erie

🚗 130 miles ⏱️ 2 hours

Visit Erie from Pittsburgh and enjoy the beautiful shores of Lake Erie, Pennsylvania's only Great Lake port, offering beaches, parks, and maritime attractions.

Presque Isle close by becomes extra lively during the winter because of the great skiing routes, so be prepared for a busier atmosphere.

Pittsburgh to Morgantown and Coopers Rock State Forest

🚗 80 miles ⏱️ 1 hour, 20 minutes

Head from Pittsburgh to Morgantown, a must-visit for fans of quaint small towns. You can dabble in water sports, hiking, and get out into the breathtaking nature nearby

Visit nearby Coopers Rock State Forest for a day of hiking, breath taking overlooks, and enjoy West Virginia's natural beauty.

Pittsburgh to Lake Arthur and McConnells Mill State Park

🚗 40 miles ⏱️ 50 minutes

A short drive from Pittsburgh, Arthur is one of the nearest notable trips from Pittsburgh and is a favorite for both long-distance tourists as well as locals.

Lake Arthur is only one small part of the much bigger Moraine State Park , which is Pennsylvania's fourth biggest State Park.

Pittsburgh to Columbus

🚗 180 miles ⏱️ 3 hours

A visit to Columbus, Ohio's capital and the biggest city, has plenty to discover and is a great place to re-energise after a drive. The city's innovative, hip, and young vibe is what draws the crowds to its happening arts and tech scene.

Along the way check out Egypt Valley Wildlife Area and Salt Fork State Park , before you reach the bustling city sites of Columbus.

Pittsburgh to Mars

🚗 25 miles ⏱️ 40 minutes

A quick trip from Pittsburgh leads you to Mars, a charming small town with unique attractions and a quaint downtown area.

Why not check out Evans City en route. This small borough has nearby attractions such as Evans City Cemetery, featured in the film 'Night of the Living Dead.'

Pittsburgh to Nashville

🚗 590 miles ⏱️ 8 hours, 50 minutes

Drive from Pittsburgh to Nashville to immerse yourself in the heart of country music. In addition to being a music capital, Nashville is brimming with historical sites, outdoor activities, professional sports and delicious food.

Before you reach Nashville make sure to enjoy interesting stops at Cincinnati and Louisville .

Pittsburgh to Sewickley

🚗 16 miles ⏱️ 25 minutes

A short drive from Pittsburgh, visit Sewickley for a taste of local culture, boutique shopping, and charming cafes in a picturesque village setting.

This quick trip also passes Robinson Township , a suburban area west of Pittsburgh, home to shopping centers and restaurants.

Pittsburgh to Hocking Hills State Park

🚗 190 miles ⏱️ 3 hours, 30 minutes

Escape to Hocking Hills State Park from Pittsburgh. A natural reserve that is filled with splendid caves, waterfalls, and quaint gorges in the shade of hemlocks. It's where Ohio's history is written in the rocks.

There is also the option to detour to Ohiopyle State Park , a little extra travel time but the chance a route that offers stunning scenery.

Pittsburgh to Cleveland and Akron

🚗 130 miles ⏱️ 2 hours, 10 minutes

Travel from Pittsburgh towards Cleveland and you can expect a buzzing metropolis with lots of action. Akron afterwards then offers a more relaxing pace as a former farming community turned industrial city.

Make sure to visit Cuyahoga Valley National Park as you pass between Cleveland and Akron.

Longer road trips from Pittsburgh

Pittsburgh to Atlanta

🚗 720 miles ⏱️ 11 hours, 50 minutes

Take a long drive from Pittsburgh to Atlanta and discover the dynamic culture, history, and southern charm of Georgia's capital.

Pittsburgh to Orlando

🚗 970 miles ⏱️ 14 hours, 30 minutes

Embark on a road trip from Pittsburgh to Orlando, the theme park capital of the world, for an unforgettable family adventure filled with magical experiences.

Pittsburgh to Bar Harbor, Maine

🚗 870 miles ⏱️ 14 hours

Journey from Pittsburgh to the picturesque Bar Harbor, Maine, via Portland. The unforgettable rugged beauty of Maine's coastline, fresh seafood, and epic Acadia National Park, will greet you.

Pittsburgh to Portland

🚗 690 miles ⏱️ 11 hours

Travel from Pittsburgh to Portland, Maine, and discover the charm of this New England city known for its lighthouses and arts scene.

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

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

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

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

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

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

Best Road Trips From Boston

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

Coastal Road Trip Destinations From Boston

1. plymouth, ma.

Distance From Boston: 40-50 minutes

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

Best things to do in Plymouth:

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

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

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

2. Cape Cod, MA

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

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

Best Things To Do on Cape Cod :

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

You may also enjoy:

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

3. Nantucket, MA

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

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

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

Best Things To Do on Nantucket:

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

4. Martha’s Vineyard, MA

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

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

Best Things To Do on Martha’s Vineyard:

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

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

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

5. Marblehead, MA

Distance From Boston: 40-50 minutes.

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

Best Things To Do in Marblehead, MA:

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

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

6. Salem, MA

Distance From Boston: 30-40 minutes.

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

Best Things To Do in Salem, MA:

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

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

7. Rockport, MA

Distance From Boston: 50-60 minutes.

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

Best Things To Do in Rockport, MA:

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

Click here for more amazing things to do in Rockport!

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

8. Newburyport, MA

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

Best Things To Do in Newburyport, MA:

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

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

9. Block Island, RI

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

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

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

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

Best Things To Do on Block Island, RI:

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

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

10. Newport, RI

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

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

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

Best Things To Do in Newport, RI:

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

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

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

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

11. Mystic, CT

Distance From Boston: 1.5 hours

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

Best Things To Do in Mystic, CT:

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

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

12. The Hamptons, NY

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

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

The Best Things To Do in The Hamptons:

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

13. Ogunquit, ME

Distance From Boston: 1 hour and 15 minutes

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

Best Things To Do in Ogunquit, ME:

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

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

14. Kennebunkport, ME

Distance From Boston: 1 hour and 25 minutes

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

Best Things To Do in Kennebunkport, ME:

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

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

15. Bar Harbor/Acadia National Park

Distance From Boston: 4 hours and 45 minutes

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

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

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

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

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

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

Luxury Road Trip Destinations From Boston

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

16. Cliff House in Cape Neddick, ME

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

What To Expect During Your Stay At Cliff House:

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

Click here to book your stay at Cliff House!

17. Ocean House in Westerly, RI

Distance From Boston: 1 hour and 45 minutes

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

What To Expect During Your Stay At Ocean House:

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

Click here to book your stay at the Ocean House!

18. Mohonk Mountain House in New Paltz, NY

Distance From Boston: 3 hours and 45 minutes

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

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

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

What To Expect During Your Stay At Mohonk Mountain House:

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

Click here to book your stay at Mohonk Mountain House!

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

19. Mirbeau Spa in Rhinebeck, NY

Distance From Boston: 3 hours and 10 minutes

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

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

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

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

Click here to book your stay at Mirbeau in Rhinbeck!

Charming Small Town Road Trip Destinations From Boston

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

20. Saratoga Springs, NY

Distance From Boston: 3 hours and 15 minutes

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

Best Things To Do in Saratoga Springs, NY:

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

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

21. Skaneateles, NY

Distance From Boston: 5 hours and 20 minutes

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

Best Things To Do in Skaneateles, NY:

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

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

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

22. Lake Placid, NY

Distance From Boston: 5 hours

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

Best Things To Do in Lake Placid, NY:

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

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

Click here to read my post on all the best things to do in Lake Placid in the fall!

23. Hudson, NY

Distance From Boston: 2 hours and 45 minutes

Located in the Hudson Valley of New York, Hudson is known as being incredibly charming, and one of the best destinations for antiquing in the area. This is a great little town to visit if you’re looking to relax, enjoy a small-town atmosphere and see where the day takes you. Hudson is also a great destination if you’re looking to explore the entire Hudson Valley region.

Best Things To Do in Hudson, NY:

• Antiquing! There are countless antique shops in Hudson, and you’ll definitely want to check out The Antique Warehouse , which has over 300,000 sq. feet of treasures.
• Stroll down Warren Street, where most of the storefronts can be found.
• Take a boat cruise along the Hudson River with Hudson Cruises , which offers tours to the Hudson-Athens Lighthouse, and even murder mystery cruises!
• The Hudson Farmer’s Market is regarded as one of the best in the region, and is open every Saturday in-season, and also has a winter location February-April.
• Tour the local art galleries.
• Go for a nature walk in the Greenport Conservation Area, which is home to over 7 miles of trails, and is walkable from downtown Hudson.

Click here to read my post on the best things to do in Upstate New York in the fall!

24. Manchester, VT

This small little town in Southern Vermont is the perfect place to disconnect and relax. As you cross the New York/Vermont border, you’ll begin to see the tall mountains all around you, and instantly feel more at peace. In fact, you’ll be able to see the surrounding mountains from everywhere in downtown Manchester. And with everything to do from shopping and dining to hiking and nature walks, you’re sure to find something that everyone in your group will enjoy.

Best Things To Do in Manchester, VT:

• Hike or drive up Mt. Equinox, the tallest mountain in the Taconic Range, and enjoy the incredible views from above.
• Browse through Northshire Bookstore , an amazing independent bookstore that’s been in business since 1976. Here, you’ll find new and used books, a wonderful children’s section, and unique Vermont-inspired gifts and souvenirs.
• Visit Hildene , the Lincoln family estate, where visitors can tour the gardens, walking trails, farm land and indoor exhibits, and enjoy sweeping views of the Vermont countryside.
• Rent a tube at Vermont River Runners and take a relaxing water tube ride along the Battenkill River, which is perfect for a warm summer day.
• Grab a sandwich as big as your head at Zoey’s Deli . I also love their homemade chips!
• Hike the Lye Brook Falls trails to visit a beautiful waterfall. The trailhead is a short 5-minute drive from town center.
• Go for a dip in the Dorset Marble Quarry for a unique swimming experience!
• After your swim, visit the Dorset Union Store , a quintessential Vermont country store.

Click here for an awesome Vermont covered bridges tour itinerary!

25. Woodstock, VT

Distance From Boston: 2.5 hours

Of all the Vermont towns on this list, I think Woodstock might be my favorite. I love them all, but there’s something about Woodstock that just screams New England charm, and perfectly balances being a town that caters to tourists, while not losing any of the local character. It’s one of those idyllic towns you’ll daydream about moving to.

Best Things To Do in Woodstock, VT:

• Walk through the truly adorable village and enjoy the local shops and coffee cafes.
• Head over to the Woodstock Middle Covered Bridge, located right in the village, for a picture-perfect Vermont moment.
• Get your hands muddy with a pottery workshop at Farmhouse Pottery .
• Drive to nearby Quechee and visit the Simon Pearce Restaurant & Mill , and take in a live glass-blowing demonstration, as well as lunch overlooking the gorge.
• Head over to Quechee Gorge Village after Simon Pearce for some antiquing.
• Visit Billings Farm & Museum to tour a working dairy farm, gardens and orchards, and see live demonstrations. The grounds here are truly spectacular!
• Hike Mount Tom for stunning views of Woodstock from above.
• Best Places To Stay In Vermont In The Fall
• Best Things To Do In Woodstock, VT
• Best Winter Getaways In New England

26. Stowe, VT

Distance From Boston: 3 hours and 20 minutes

Stowe is an adorable little village in Northern Vermont that I love to visit, and it always puts a smile on my face. Even though it’s a well-known ski destination in the winter months, it’s a great little place to visit year-round will lots of outdoor activities and perfect Vermont scenery all over, including some beautiful covered bridges.

Best Things To Do in Stowe, VT:

• Hike Mount Mansfield, the highest mountain in Vermont, or drive the auto road to the summit.
• See if you believe in ghosts at Emily’s Covered Bridge. Legend says it’s haunted by a girl who hung herself on the bridge after her boyfriend never came to meet her.
• Walk the Stowe Recreation Path, a 5.5-mile long paved path that goes through beautiful scenery throughout the village. The path can be accessed from several locations in the village.
• Connect to the Quiet Path along the Rec Path, which is reserved for walkers only (meaning, no bikes wizzing by you). It meanders through parts of Mayo Farm, and is a very relaxing way to spend an afternoon.
• Go hiking at Smuggler’s Notch State Park.
• Visit the nearby Ben & Jerry’s Factory for a tour.
• Explore Sterling Falls Gorge.
• In the winter, hit the slopes at Stowe Mountain Ski Resort.
• Pick up some chocolates from Lake Champlain Chocolates.
• Best Things To Do In Stowe, VT
• Best Stops To Make When Driving From Boston to Stowe, VT
• Best Things To Do In Vermont In The Winter

27. Greenwich, CT

Distance From Boston: 3 hours

Greenwich is an absolutely beautiful town that sits right on the border of New York, and also very accessible to Manhattan. I love coming to this idyllic little town when I want a day of relaxing, shopping, dining, being outside, visiting the beach and enjoying the gorgeous scenery.

Best Things To Do in Greenwich, CT:

• Shop the stores along Greenwich Avenue.
• Enjoy a serene walk through the Donald M. Kendall Sculpture Gardens in nearby Purchase, NY.
• Meander through Montgomery Pinetum, a public park that’s very relaxing, and also has beautiful ponds, nature trails and gardens with an educational center and greenhouse.
• Head to the Lobster Bin for an amazing lobster roll on-the-go.
• Spend some time at the beaches along Greenwich Point Park.
• Admire the architecture of the historic district buildings.

28. Jackson, NH

Let’s head to the White Mountain National Forest in New Hampshire! One of the best towns to stay in is Jackson, where you’ll find a lovely downtown and Main Street, an iconic red covered bridge, and endless opportunities to explore the White Mountains region, including lots of hiking and outdoor activities. While it’s most popular during the winter for skiing, and the fall for foliage season, Jackson can be enjoyed year-round.

Best Things To Do in Jackson, NH:

• Visit Honeymoon Bridge, the town’s famous red covered bridge.
• Drive to the summit of Mount Washington, the highest peak in New England.
• Hike the Glen Ellis Falls Trail.
• Explore the downtown shops and restaurants.
• In the winter, go skiing at Black Mountain. In the summer, the mountain offers horseback riding and lots of hiking trails.

You may also like: The best things to do in New England in the fall!

City Life Road Trip Destinations From Boston

Even though you’re road-tripping from a city already, it’s still exciting to explore a new one. There are quite a few cities that make for amazing road trips from Boston, and many of them can be combined with other destinations from this list to offer the best of city life, and coastal or small-town living.

29. Portsmouth, NH

Distance From Boston: 1 hour

This charming little city is just a short drive from Boston, and definitely feels more like a town than a city. Portsmouth is a port-side city with a gorgeous downtown filled with quaint shops and boutiques, and is known as being a huge foodie destination. This is a great city to visit if you’re looking for a lot of character, and lots of options when it comes to being outside, dining and shopping.

Best Things To Do in Portsmouth, NH:

• Grab some fresh and delicious pastries from Elephantine Bakery , and be sure to enjoy them just outside the cafe in the most adorable little courtyard.
• Shop the boutiques in downtown Portsmouth.
• Walk along Prescott Park, which has over 10 acres of waterfront gardens and paths, and is home to live entertainment in the summer months.
• Take a dip in the water at Great Island Common Park.
• Go brewery hopping, as Portsmouth is home to five breweries.
• Enjoy a drink at the Book & Bar , a combined bookstore, cafe and bar.
• Head out onto the water with Portsmouth Harbor Cruises .
• Visit Portsmouth Harbor Lighthouse.

30. Providence, RI

Providence is the capital of Rhode Island, and also home to famed schools Brown University and the Rhode Island School of Design. It’s also a really fun city to be a tourist! With Providence River running through the city, you still have opportunities to feel like you’re connected to nature, and with tons of restaurants, shops, nightlife and history, this destination makes for an amazing road trip from Boston.

Best Things To Do in Providence, RI:

• Visit The Arcade , the country’s very first shopping mall designed with Greek revival architecture, and now home to some awesome boutiques and art galleries.
• Visit the Roger Williams Park Zoo , which is the third oldest zoo in the country, where guests can feed giraffes and other farm animals, and see over 160 different species while visiting. You can also jump on the Explore and Soar ride, which is a fun zip ride and train excursion through the forests.
• Enjoy a leisurely walk along the Providence Riverwalk.
• During the summer, experience WaterFire, where braziers are set with bonfires in the middle of the river.
• Take in the exhibits at the RISD Museum of Art.
• Take a Venetian gondola ride along the river at Waterplace Park.
• Do a self-guided historical walking tour along Benefit Street to see some of the city’s most historic houses and buildings.
• Take a boat tour along the Providence River.

Click here to read my post on the best day trips from Providence!

31. Portland, ME

Portland is an exciting waterfront city in Maine that sits on a peninsula along Casco Bay, and provides the best of both worlds as far as being a city destination that’s also coastal. With things to do outdoors along the dramatic coastline, to an amazing restaurant and food scene, Portland has a little something for everyone during your road trip from Boston.

Best Things To Do in Portland, ME:

• Portland Head Lighthouse is a must! It’s the most famous lighthouse in Maine, and one of the most iconic in all of New England. Nearby, you can also visit Spring Point Ledge Light and Bug Light, and do a mini lighthouse tour without leaving the city!
• Visit one of my favorite breweries in New England, Bissell Brothers . They also get bonus points for being close to the waterfront at Thompson’s Point.
• Meander around Old Port to see the city’s fishing industry come to life.
• Walk along the lively waterfront scene on Commercial Street for shopping, dining and water views.
• Tour the open waters on a beautiful Schooner tour with Portland Schooner . They also invite you to pack a picnic with beer and wine to enhance your experience.
• Tour the Portland Arts District, which is filled with art galleries, museums and theaters.
• Take a culinary tour of the city and learn the very best places to eat, led by a local. Click the link below to book your tour, or learn more info.

Click here to book your walking culinary tour in Portland!

You may also like:

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32. New York City

Distance From Boston: 3 hours and 45 minutes (but always allow extra time for traffic)

New York City needs no introduction, and if you’ve never been to the city that never sleeps, this is an absolute must if you’re looking into road trips from Boston. Below is a list of my absolute favorite things to do when I visit NYC, which includes the best things to do for first-time visitors.

The Best Things To Do in New York City:

• Walk the Brooklyn Bridge and visit DUMBO for sweeping views of both the Brooklyn and Manhattan bridges.
• Get bagels at Brooklyn Bagel (the best in the city).
• Visit Central park, and be sure to stop at Bow Bridge, Belvedere Castle and The Mall walkway.
• Grab a slice of pizza at Joe’s (150 E 14th St.)
• Explore the MET Museum and Cloisters.
• Take the Staten Island Ferry for views of the Statue of Liberty (this is free and way better than the official tours, which are super crowded!).
• See a broadway show.
• It’s touristy, but I love going to the top of the Empire State Building.
• Walk around the West Village for amazing streets and brownstones.

33. Burlington, VT

Burlington is a small and beautiful city in Northern Vermont that sits along Lake Champlain, and is wonderfully diverse, exuberant and also very relaxing. This is a great destination if you’re looking for a small-town feel set in a bigger city, waterfront and outdoor activities, an art scene and plenty of amazing restaurants.

Best Things To Do in Burlington, VT:

• Walk around Church Street, a pedestrian-only area lined with unique shops and restaurants.
• Stroll around the waterfront to admire the views of Lake Champlain, as well as the Burlington Breakwater Lighthouse.
• Bike the Burlington Bike Path, a beautiful path along the lake that’s over 7 miles long.
• Go kayaking or stand up paddleboarding on the lake.
• Head to nearby Shelburne to tour Shelburne Farms , one of my favorite things to do in all of Vermont! There are tons of hiking and walking trails through the 1400-acre picturesque grounds, and you can stop to sample their homemade cheeses and baked goods along the way.
• Take in the art scene on the South End, which is loaded with galleries and shops.
• Get a taste for the local brews with a Sip of Burlington Beer Tour. Join a small group for dinner, and learn from a local brew expert as you taste all the different beers that are brewed nearby. Click the link below to learn more, or book your tour.

Click here to book your Beer of Burlington experience!

34. Philadelphia, PA

Last but most definitely not least on our round-up of the best road trips from Boston, is the city of Brothery Love, Philadelphia. Philly is Pennsylvania’s largest city, and is deeply rooted in history, but there are all kinds of things to do from exciting nightlife and amazing food to parks and waterfront activities.

Best Things To Do in Philadelphia, PA:

• Run up the Rocky Steps at the Philadelphia Museum of Art, and snap a picture with the Rocky statue. A bit touristy, but if you’re a fan of the movie, you gotta go for it.
• Speaking of the Philadelphia Museum of Art , after your Rocky moment, be sure to visit. They have an amazing American art collection, as well as works by famed impressionists Renoir, Degas and Monet.
• Tour Independence Hall, regarded as the birthplace of the United States, and where the Declaration of Independence was debated by our Founding Fathers.
• Venture just outside the city to visit Longwood Gardens, an expansive garden oasis filled with both indoor and outdoor gardens and, and beautifully designed grounds.
• Grab a Philly cheesesteak at Woodrow’s Sandwich Shop .
• Stroll along the Delaware Riverfront to explore Cherry Street and Race Street Piers, and take in amazing views of the Benjamin Franklin Bridge.
• Hop on a BYOB trolley tour of the city, hosted by hilarious guides that share historic and entertaining information, and take you to some of the top sites in the city. Click the link below to learn more, or book your tour.

Click here to book your Historically Hilarious Trolley Tour in Philadelphia!

Road Trip Itinerary Options

If you’re looking to combine towns from this list into longer roads trips, or are wondering which towns are close enough to combine together to maximize your time and cover the most ground, I’ve got you covered! Below you’ll find suggested itineraries with different routes you can take while planning the best road trips from Boston.

Option 1: Massachusetts North Shore Road Trip From Boston

For this route, you’ll head north from Boston and visit the following destinations:

• Newburyport & Plum Island
• Portsmouth, NH

Days Needed For This Route: 2-4 . If you’re looking for an easy road trip from Boston with lots of options, this is an awesome route to take. You can do it in as little as 2 days for a weekend trip, or add on two additional days to take your time and explore each town.

Option 2: Cape Cod & The Islands Road Trip From Boston

For this route, you’ll head south from Boston and visit the following destinations:

• Martha’s Vineyard

Days Needed For This Route: 7-8 days. Because this route requires ferries from Cape Cod to the islands, and with Cape Cod being a larger region to explore, I recommend a week.

If you have less time, the islands could be done as day trips, and you could attempt this route in about 5 days . If you have 10 days, I would suggest spending one night in Plymouth, 5 days on Cape Cod, two nights on Nantucket and two nights on Martha’s Vineyard for the ultimate Cape Cod road trip.

Option 3: Boston To Bar Harbor Road Trip

This route will take you up the coast of Maine and stop in these destinations:

• Newburyport, MA
• Ogunquit, ME
• Kennebunkport, ME
• Portland, ME
• Bar Harbor, ME

Days Needed For This Route: 7-10 days. I suggest this much time because your final destination, Bar Harbor, is home to Acadia National Park, and there’s so much to see and do just in the park. And each stop along the way is a very worthy destination to spend at least one night in.

If you’re very short on time, you can do this route in 4 nights with this itinerary:

• On your way to Ogunquit, pass through Newburyport and spend 2-3 hours there. Arrive in Ogunquit late afternoon to spend the night.
• The next day, spend the morning in Ogunquit, and then drive to Kennebunkport to spend about 3 hours exploring there. Drive to Portland, and spend the night.
• The next day, spend your morning in Portland, and then drive to Bar Harbor to arrive by mid-afternoon. Spend 2 nights in Bar Harbor.
• Drive back to Boston.

I have a detailed Boston To Bar Harbor, Maine Road Trip Itinerary if you’d like more help with planning!

Option 4: Vermont Road Trip From Boston

For this route, you’ll head northwest of Boston, and drive through the best towns in Vermont from this list. You’ll cover these destinations:

• Manchester, VT
• Woodstock, VT
• Burlington, VT

Note : This route isn’t as direct as the other routes, and will include 6.5 hours of driving time to get from Boston to Burlington, stopping at the other destinations along the way. But then you can drive direct from Burlington to Boston on your way home, which will only take 3.5 hours.

Days Needed For This Route: 3-5 days . This could easily be a long weekend itinerary if you don’t stop in each town overnight, and just visit Manchester and Stowe for a few hours each. You could, of course, take your time, and do up to 5 nights for this itinerary.

Option 5: Rhode Island & Coastal Connecticut Road Trip From Boston

This route will take you southwest from Boston, and you’ll visit these destinations:

• Providence, RI
• Newport, RI
• Block Island, RI
• Westerly, RI

Days Needed For This Route: 3-6 days . This is another itinerary you could also do in a weekend if you only spend a few hours in Mystic, as a day trip from Newport, and skip going to Block Island. To visit all these destinations, you’ll need about 5 days, but 6 would be ideal to not feel rushed.

Tip : If you wanted to extend your road trip further along this route, there is a ferry that leaves from New London, CT, and goes to the Hamptons!

Option 6: Boston To New York City & The Hamptons Road Trip

This route will take you to these destinations:

• Rhinebeck, NY
• New Paltz, NY
• New York City
• The Hamptons
• Optional add-on: Philadelphia, PA

Note : The route from Boston to The Hamptons, while making all the stops in the Hudson Valley in-between, is not direct, and will take about 7.5 hours without stops, so I highly suggest you stop overnight in at least one of the towns to break up your drive. If you wanted to visit Philadelphia, this would be the route you would want to add that destination to, as you will have to drive through NYC to get there.

Days Needed For This Route: 1 week. To do this route in 7 days, I would suggest spending a few hours each in Hudson and Rhinebeck, then spend the night in New Paltz (splurging at Mohonk Mountain House is definitely worth it!). Then drive to NYC the next day, and spend 3 nights there. Then drive to The Hamptons, and spend 3 nights. If you want to add Philadelphia, you’ll want to add an extra night or two.

If you’re short on time and want to do this route in fewer days, I would suggest spending a night in the Hudson Valley (same as above), spend 3 nights in NYC, but include a day trip to The Hamptons. Or, if The Hamptons is of more interest to you, you could spend one night in NYC, and spend a night or two in The Hamptons. And then drive back to Boston.

The other option is to drive direct from Boston to New York City, and leave out the Hudson Valley towns entirely. On that route, your focus would be New York City and The Hamptons.

What Towns Are 1 Hour From Boston?

Plymouth, Salem, Rockport, Newburyport are all within an hour from Boston, and make for wonderful road trips or day trips from Boston.

Towns not mentioned on this list that are also an hour or less from Boston that are perfect for a road trip are Scituate, Gloucester, Manchester-By-The-Sea and Essex, all of which are located in Massachusetts.

What Cities Are 6 Hours From Boston?

New York City, Portsmouth, NH, Philadelphia, PA, Portland, ME, Burlington, VT and Providence, RI are all within 6 hours or less from Boston, and are all included on this list as amazing road trips from Boston.

Is Boston Close To Niagara Falls?

Boston is over 7 hours from Niagara Falls, and for that reason, didn’t make this list of road trips. But if you have extra time, it could be added to a road trip itinerary for Skaneateles, NY and the finger lakes region.

• 7-Day New England Road Trip Itinerary
• The Perfect New England Fall Road Trip
• Boston In The Fall: Fun Things To Do!
• The Best New England Gifts and Souvenirs to Look For During Your Trip
• 60+ Things To Do In Vermont
• Summer In New England: Best Places To Go & Things To Do!
• Incredible New England Resorts & Spas
• Best Time To Visit New England

That’s A Wrap On The Best Road Trips From Boston

As you can see, Boston is really an incredible gateway to all of the Northeast, making it easy to take lots of different road trips. Whether you want to explore the coast of Massachusetts and Maine, go cute-town-hopping through Vermont or visit as many cities as you can, you’re now ready to plan which of these road trips from Boston is perfect for you.

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The cost of driving from Boston, Massachusetts to Pittsburgh, Pennsylvania is:

$82.80 one-way / $165.59 round trip.

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Route to drive from Boston, MA to Pittsburgh, PA

View a map with driving directions using your preferred map provider: Google Maps , Bing Maps , or MapQuest . You can use CostDrive.com to get the cost to drive from Boston to Pittsburgh .

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The total cost of driving from Boston, MA to Pittsburgh, PA (one-way) is $82.80 at current gas prices.

The round trip cost would be $165.59 to go from Boston, MA to Pittsburgh, PA and back to Boston, MA again.

Regular fuel costs are around $3.63 per gallon for your trip. This calculation assumes that your vehicle gets an average gas mileage of 25 mpg for a mix of city and highway driving.

All currency units are U.S. Dollars. If you prefer international units, the equivalent petrol pump price is 95.8 cents/litre . This assumes a typical fuel economy of 9.4 L/100 km .

You'll go through 22.8 gallons of gas during this trip. This is equal to 86.5 litres .

If you fill your tank with unleaded gasoline, the carbon emissions will be around 447 lbs CO2 . This is equivalent to 203 kg CO2e or 0.20 tonnes of carbon dioxide equivalents. These numbers may change depending on the exact make and model of your car. If your vehicle uses diesel instead, the CO2 emissions will be around 523 lbs CO2 , which is equivalent to 237 kg CO2e or 0.24 tonnes of carbon dioxide equivalents.

These results are based on the actual driving distance from Boston, MA to Pittsburgh, PA, which is 571 miles or 919 kilometers .

Your trip begins in Boston, Massachusetts. The price of regular gas is currently averaging $3.58 in Massachusetts .

Your trip ends in Pittsburgh, Pennsylvania. The price of regular gas is around $3.67 in Pennsylvania .

Currently, we only have exact data for locations in the United States. To improve the accuracy of your fuel cost estimate, you can enter the actual price you pay for gas or petrol at the local pump in the table above.

The following chart displays the difference in total cost of driving given varying fuel grades. If your car requires higher octane gas, you can find out how much more it will cost you to drive between Boston, MA and Pittsburgh, PA.

Boston, Massachusetts

Related links.

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Pittsburgh, Pennsylvania

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Cost of driving

Travelmath provides an online driving cost calculator to help you determine how much you'll spend on gas for your next road trip. You can enter airports, cities, states, countries, or zip codes to compute the cost of driving between locations. Driving distances are calculated using actual driving directions if they are available, or a GPS-accurate method for the straight line distance. Automatic estimates are provided for local gas prices and vehicle fuel efficiency in miles per gallon (mpg) or liters per 100 kilometers (L/100 km), based on the make and model of your car, SUV, or minivan. Don't let the economy and rising oil prices stop you from taking your next trip. You can use this tool to find out if it's cheaper to fly or drive to your destination.

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Lee the Horselogger makes his way through Cheyenne on his way to Boston

CHEYENNE, Wyo. (Wyoming News Now) - “I travel to see nursing homes to meet people, go to schools, I do my show and tell, this is a horse, you know a lot of people have never seen a horse”, says Lee the Horselogger.

Lee the Horselogger left East Glacier, Montana August 6, 2006 and has traveled across the United States 4 times with a horse and carriage.

Lee, who is accompanied by his horse Jessie are on their current 5th trip across the United States and they made their way through Cheyenne Wednesday, May 8.

When asked why he takes his trips, lee states the following, “(I am) 63 years old, I don’t have any family, so I figured why the hell not, see what goes on in the world”.

Last September Lee’s original carriage was struck in an accident, but that did not stop Lee from making his fifth cross country road trip this year.

Lee and Jessie can only travel around 3 miles per hour, so when asked what makes his day he says when people give him space to travel.

“That’s the biggest issue for me, just give me enough room, I’m driving but also I’m like anybody who’s driving”, said Lee.

They are currently on their way to Boston, Massachusetts, and while they have a long way to go Lee says the experience is “one he will never for-go”.

Copyright 2024 KGWN. All rights reserved.

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Boston traffic is a nightmare. Here’s a guide to help you master it.

It’s almost certainly urban legend that Boston’s roads are so circuitous because they are paved-over cow paths. But the humans who did design them weren’t doing modern-day drivers any favors.

Finding yourself in the wrong lane at the infamous Braintree Split can be the difference between ending up in Canton or barreling toward the Cape. A simple 5-mile trip to the airport could send you on an interstate, atop a bridge, and through an underwater tunnel. And God forbid you need to navigate within the city in a U-Haul on move-in day (more on that later).

It’s a wonder we ever leave our driveways — especially if you’re new to the city and its dogpile of thoroughfares. Sure, Google Maps or Waze can (probably) direct you from Point A to Point B. But it’s worth understanding the basics of Boston’s grid — or lack thereof — before you get behind the wheel.

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“I have found that when I need to get somewhere into the city, you really do have to have a very intense knowledge of where all of the streets and roads go to,” said Kristen Eck, the helicopter reporter for WBZ NewsRadio, who has been reporting on Boston traffic from a 900-foot bird’s eye view for over two decades.

So we put together a new driver’s guide to Boston traffic, with a breakdown of the basics: the major roadways, bridges, and tunnels, as well as some neighborhood-specific insights.

Highways and bridges and tunnels, oh my!

Perhaps the most notorious highway in these parts is Interstate 93 , the north-south route that stretches from the Dunkin’ capital of Canton, through downtown Boston, up into Somerville and Medford, and on to New Hampshire.

I-93 was the focus of the oft-bemoaned Big Dig , the mega-project that took an elevated slice of the highway downtown known as the Central Artery and shoved it underground into the newly constructed O’Neill Tunnel .

Then there’s a portion of I-93 that runs from downtown Boston to Braintree known as the Southeast Expressway . Unless you like hours-long traffic jams, avoid it at all costs.

“That really is the worst road in the state,” said Eck. “If you’re a morning commuter coming in from south of the city, if you don’t get to that highway by five o’clock in the morning, you’re going to be sitting on it at some point.”

Moving right along: The Big Dig also gave us the Zakim Bridge , the wishbone-shaped overpass that carries I-93 across the Charles River between Boston and Charlestown, and the Ted Williams Tunnel , which travels from South Boston to East Boston underneath the Boston Harbor.

If you need to go to the airport from Boston, you’ll either take the Ted Williams or the Callahan Tunnel , which begins in the North End. Coming back to Boston from the airport, you’d either take the Ted Williams or the Sumner Tunnel ( if it’s open, that is ).

Another portal to the north (Revere, Saugus, Danvers, etc.) is Route 1 , perhaps best known for being the home of the beloved tiki-themed Kowloon Restaurant. Route 1 also means crossing the Tobin Bridge , the hulking green monstrosity that spans the Mystic River between Charlestown and Chelsea.

Heading east-west, we’ve got Interstate 90 , which in local parlance is known as the Massachusetts Turnpike , or simply the Pike . It’s the highway with “the greatest chance of you actually getting a morning off from traffic,” according to Eck. In case you were wondering, The Ted Williams Tunnel is technically part of the Pike. (Is your head spinning yet?) The Pike also runs next to Fenway Park.

For a gorgeous vista of the Boston skyline, take a trip over the Longfellow Bridge , which crosses the Charles River from Kendall Square to Beacon Hill. This suggestion is courtesy of Mike Garvey, a cab driver with Green Cab and Yellow Cab of Somerville who has been taxiing people around the city since 1990. “It’s just a nice scenic, quick, smooth ride right into Mass. General or to Government Center, to the North End,” he said.

If you’re looking to travel in the city’s western outskirts, the two main interstates are Interstate 95 and Interstate 495. Most of I-95 near the Boston area can also be referred to as Route 128 (don’t think too hard about it), and it encircles close-in Boston suburbs like Dedham, Newton, and Lexington. Around Peabody, on the North Shore, Route 128 officially breaks off of I-95 and heads on its own toward Cape Ann.

Further afield, I-495 traces municipalities like Mansfield, Marlborough, and Lowell. “Greater Boston” is a loosely defined region, but if a town is inside the so-called 495 loop, chances are it qualifies.

Other roads to know

Outside of the major interstates, there are some local roads you should keep in your mind’s GPS.

In both Boston and Cambridge, there are the “river roads,” which trace the Charles River — though they (unhelpfully) change names several times en route.

On the Cambridge side, Memorial Drive begins around Kendall Square before jutting out and turning into Fresh Pond Parkway northwest of Harvard Square, then becoming Alewife Brook Parkway , which winds into Somerville and then becomes Mystic Valley Parkway , and on, and on...

On the Boston bend, Storrow Drive kicks off around Beacon Hill before transforming into Soldiers Field Road as it travels into Allston–Brighton.

Never, ever, ever get on Storrow Drive if you’re in a U-Haul or other large truck, lest you end up an item in the next day’s Globe. Thank us later.

The river routes aren’t the only roads with something of an identity crisis. Many of the area’s main thoroughfares carry official state highway names — for instance, Massachusetts Avenue in Boston and Cambridge might show up as Route 2A on Google Maps, and the Monsignor O’Brien Highway/McGrath Highway in Cambridge and Somerville may carry Route 28 signage. Don’t fret, you have not lost your way.

By and large, you should call surface roads by their non-numerical names — and a lot of them are truncated even further:

• Commonwealth Avenue = Comm. Ave.
• Massachusetts Avenue = Mass. Ave.
• Dorchester Avenue = Dot. Ave.
• Blue Hill Avenue = Blue Hill Avenue (hey, they can’t all have fun nicknames.)

If it’s any consolation, there are pockets of logic in all the chaos. In Back Bay, for instance, the streets are laid out in a grid for a stretch. “The cross streets that go across Comm. Ave. and Newbury Street and Beacon Street, they all go in alphabetical order,” said Eck. It goes: Arlington Street, Berkeley Street, Clarendon Street, Dartmouth Street, Exeter Street, Fairfield Street, Gloucester Street, and Hereford Street. (Then there’s a gash, with the alphabet continuing in the Fenway neighborhood — it’s a long story.)

If all else fails, Eck says, there is one tried-and-true method to getting more comfortable with the city’s layout: walking.

“If you try to throw yourself into Boston traffic full-speed, rush-hour, in a car, you might find yourself overwhelmed,” she said. “Whereas if you can find half an hour, maybe even an hour, to go out for a walk every day and block a new set of streets and see where they go, I think that’s really helpful.”

Have a tip to add? Join the conversation through the No Stupid Questions newsletter on LinkedIn .

Read more from the Globe’s No Stupid Questions series:

• Deciding where to live? Here’s your Greater Boston Neighborhood Vibe Check™.
• Taxes are a pain. Here’s how to make them a less expensive pain if you live in Massachusetts.
• How to find a good mechanic, dentist, or dry-cleaner in the Boston area (Hint: it’s not just Google)
• New to the Boston area? Here’s the best advice our readers have to share.

Dana Gerber can be reached at [email protected] . Follow her @danagerber6 .

Unforgettable Boston To Bar Harbor, Maine Road Trip Itinerary

I f you’re here, that means you’re probably planning an epic New England road trip along the coast, and man, I’m SO excited for you! Hi, my name is Sam, and I’ve been exploring this corner of the world for over 10 years now. I’ve taken countless road trips along the coast, and I’ve finally perfected my unforgettable Boston to Bar Harbor, Maine itinerary for those looking to explore the  New England coast .

To date, this is my favorite road trip I’ve done, and I can’t wait for you to experience it for yourself. To help you plan the perfect adventure, I’m going to share all my expertise on this area with you, offer my best tips for planning your trip, and give you my ultimate itinerary that was years in the making.

While following along, I encourage you to tailor this itinerary to your own preferences depending on how much time you have for your trip, but I do make suggestions on how long it takes to make the drive, and see all the best places on the way.

Are you ready to start planning together? Let’s go!

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 .

Road Tripping From Boston To Bar Harbor – The Basics

Before we jump into the itinerary, let’s get started with some questions you may have …

How Long Is The Drive From Boston To Bar Harbor?

If you don’t make any stops at all, and take the most direct route, the drive takes between 4 hours and 40 minutes to 5 hours, and spans about 280 miles. It could be longer depending on traffic getting out of Boston. If you happen to leave Boston during rush hour, definitely expect it to take a bit longer.

However, if taking a road trip, you could really make this drive as long as you wanted because there are so many amazing things to see along the way, and some fun detours to take. In just a sec, I’ll give you my suggestions on how long you need to make this trip and see as much of the coast as you can 😉

The auto road to the Cadillac Mountain Summit in Acadia National Park.

Is The Drive Scenic?

I think so, yes! But it kind of depends on your expectations.

While many parts of the actual drive are on highways that are kind of boring, there are  so  many great places to stop along the way that can make the drive very scenic.  Especially  if you take some of my suggested detours and scenic byways! But is every second of the drive stunning? Well, no. So it’s good to set expectations. It’s really more about the stops you make during the trip than the actual drive itself.

There are some portions of the actual drive that are very beautiful, though.

How Many Days Do You Need To Drive From Boston To Bar Harbor?

Since there are just tons of incredible things to see, I’m recommending one week, or 7-8 days, as I know that this is how much most people have to make this drive. If you have longer than a week, then I say it’s worth it to enjoy going at a slower pace. But you can definitely enjoy the top things to see in a week. This will also include two days in  Acadia National Park!  For my itinerary, I’m mapping out 8 incredible days for you, and you can adjust it to fit your schedule 😊

Best Time Of Year To Drive Boston To Bar Harbor

Generally,  June-September  is the best time to drive from Boston to Bar Harbor, as this is when you can expect the  best weather, and longest days .  July and August is considered peak season  along the New England coastline, so this is also when you can anticipate the most crowds and highest hotel prices. But gosh, it’s so worth it!

However, I’ve done this road trip in all seasons – yep, in spring, summer, fall, and even winter! As a second suggestion, I love  May to avoid some of the crowds  and still enjoy mild weather, and also  October to chase all the stunning fall foliage .

I’m going to give you some suggestions later in the post to turn this drive into a fall foliage adventure, so be sure to check that out if you’re planning your trip in the fall season 🍁😉

It’s also good to know that some places along the New England coast are seasonal, especially seafood shacks, boat tours, and ice cream places. If they’re seasonal businesses, it’s likely they won’t open until late May or June and begin to close down around Labor Day or only stay open possibly mid-October. But you’ll always be able to find places that are open year-round, too.

How Many Days Should You Spend In Acadia National Park?

Speaking of Acadia, that’s probably the reason you’re making this drive, right? This park is undoubtedly the top attraction in New England, and rightfully so. I always recommend a minimum of two days to explore, allowing 1 full day in the park, and then at least a half day to see Bar Harbor, which is such a charming town along the coast.

If you have more than a week for this trip, you could definitely add an extra day to Bar Harbor so you have two full days to explore the park.

Is There A Ferry From Boston To Bar Harbor?

No, there is no ferry that goes between Boston and Bar Harbor. The best way to make the trip is to drive.

The only ferry to Bar Harbor is the one from Nova Scotia, which is the CAT Ferry.

Is It Worth Going All The Way To Bar Harbor?

Oh yes! I often get asked this because Bar Harbor is pretty far up the Maine coast, and it’s one of the top attractions most out of the way in New England. But yes, it’s absolutely worth the drive. Because there are so many great things to see along the way, and since Acadia offers some of the best and most iconic coastline views in the Northeast, it’s very much worth the effort.

Overview: Best Stops To Make When Driving Boston To Bar Harbor

These are the top places I recommend stopping in that I think are very much worth your time. Some of them require a bit of a detour, but depending on your preferences, you’ll probably be happy you went out of your way!

→  Massachusetts North Shore : This includes Marblehead, Salem, Gloucester, Rockport, Ipswich, and Newburyport. I suggest you drive the Essex Scenic Coastal Byway on your way to or from Bar Harbor to see some of these towns, depending on which appeals to you the most. I have a slight preference for Salem, Marblehead, and Rockport, which are all small and easy to do in a couple of hours each. I’ll go more into this later in the post 😉

→  Portsmouth, New Hampshire : Pretty much just off I-95 and not out of the way at all, Portsmouth is a charming coastal city that feels more like a quaint town. Great historic New England scenery and shopping! I recommend this stop if you’re looking for more of a town vibe vs. coastline, as the coastal views here aren’t as impressive as the rest of the places on this list.

→  Southern Maine Coast : This includes places like York & Cape Neddick, Kennebunkport, and Ogunquit. I usually suggest stopping at Nubble Lighthouse in York, spending a couple of hours each in Kennebunkport and Ogunquit, and even staying the night in one of these two towns.

→  Portland, Maine : The state’s largest city is filled with lots of maritime charm, amazing dining, lighthouses, and history. If you like cities, this may be worth staying a night, but you can also see the highlights in a few hours if you’re not a city person.

→  Freeport, Maine : Home to the flagship L.L. Bean store! It’s not worth it for everyone to stop, but gosh, it’s a pretty cool place to see if you’re looking to pick-up some New England clothing and accessories.

→  Maine’s Midcoast : Between Freeport and Belfast, just before getting to Bar Harbor, there are lots of great towns along the coast to explore in this region, including Harpswell, Boothbay Harbor, Wiscasset, Rockland, and Camden. I have so many suggestions for hidden gems and places to visit along this portion of the drive, which I’ll go more into during the itinerary portion of the post!

The PERFECT Boston To Bar Harbor, Maine Road Trip Itinerary

Overview of this itinerary:.

Since most people reading this will need to start and end their trip in Boston to catch a flight, that’s how I’m formatting the itinerary. You’ll be making most stops on the way to Bar Harbor, but also saving a few for the drive back so you have something to look forward to 😉

Day 1 : Explore Boston.

Day 2 : Get an early start and drive to either Kennebunkport or Ogunquit. Spend 1 night.

Day 3 : Drive to Portland to explore for a few hours, and then make your way to Camden with a few optional detours for lighthouses and great coastal scenery! End in Camden to spend the night.

Day 4 : Spend the morning in Camden, and then drive to Bar Harbor. Enjoy downtown Bar Harbor and grab dinner. Spend two nights here.

Day 5 : Explore Acadia National Park during the day, and more of Bar Harbor at night.

Day 6 : Drive to Boothbay Harbor to spend 1 night. Take a boat tour.

Day 7 : Drive to Portsmouth and spend a few hours enjoying the shops, and drive the Essex Scenic Byway along the Massachusetts North Shore to make your way toward Boston. Stay the night in this area.

Day 8 : Arrive back in Boston to head home.

Day 1: Explore Boston

Boston is the perfect starting point for most New England itineraries, but it’s also one of the top places to explore in the region, so you should definitely plan at least a full day in the city!

Rooted in history, packed with New England charm, and filled with exciting dining and cool things to do, you can actually cover a lot of ground in just a day in Boston, including the top highlights.

Here are some of the top things I suggest first-timers do :

→ Take a food tour to get a taste of what this region is all about. I have a detailed guide on all the  best Boston food tours  to help you pick the best one! But seafood and Italian cuisine are especially great here.

→  Visit the most charming neighborhoods , which are  Beacon Hill  and the  North End . The North End is also where you’ll find the best Italian restaurants.

→ Stroll through the  Public Gardens  and  Boston Common . The Boston Public Garden was the very first in the U.S., and it’s so beautiful and photogenic 😍 Boston Common isn’t as scenic as the Public Garden, but in the fall during foliage season, it’s on fire with color. Plus, they’re both really close to one another.

→ If you’re looking to do some  shopping , head to  Newbury Street  and  Copley Place .

→ Visit the  New England Aquarium .

→ Explore parts (or all!) of the  Freedom Trail , which is a walking tour that takes you to historically significant places around Boston. You can also take  this awesome Freedom Trail tour .

→ Grab lunch or coffee at the beautiful and Instagram-worthy  Tatte Bakery , which has locations around the city (you’ll see why I recommend it when you walk in 😉).

→ End your day with a nice dinner out. I love  Neptune Oyster , but they don’t take reservations, and it can be a long wait time. If that’s not worth it for you, I also love the  Union Oyster House  for a traditional New England dining experience. But there are so many fantastic places in Boston to choose from.

How To Get Around Boston :

Boston is very walkable, and most of the tourist attractions, which are truly the top things to see in the city, are within walking distance to one another (less than a mile) in the downtown area. If you’re exploring for a day, you likely won’t need to use public transit, but may want to get an Uber or Lyft, which are widely available, just to save time (or if you’re tired!).

Where To Stay In Boston :

All of these suggestions are in great locations, and within walking distance to most everything!

→  Boston Harbor Hotel

→  Revere Hotel Boston Common

→  The Godfrey

Day 2: Drive To Southern Maine

First thing’s first, you’ll want to  pick-up your rental car in Boston  early in the morning. Then, head out to start your drive to southern Maine! During this part of the trip, you’ll pass through Portsmouth, New Hampshire, but don’t worry, we’re going to stop there on the way back 😉 To get to southern Maine, you’ll hop on I-95.

So, Ogunquit or Kennebunkport ?  Well, you can do both if you want! Ogunquit is about 25 minutes south of Kennebunkport, and the biggest difference, as mentioned, is that Ogunquit is more of a beach town, whereas Kennebunkport is more of a coastal town. That said, Kennebunkport also has beaches, and Ogunquit is also just as charming – I honestly love both.

Since you’ll pass by Ogunquit on your way to Kennebunkport, you can stop by for a few hours and see the beach, and the cute little town, and then end in Kennebunkport. You’ll want to decide which town to spend the night in – both have plenty of hotels and dining options.

On your way to Ogunquit and Kennebunkport, I also recommend you stop in York , which is just south of Ogunquit.

Notable stops to make in York if you have time :

• Nubble Lighthouse on Cape Neddick  – the lighthouse itself is not accessible, as it’s on its own little island, but the viewpoint is really great and worth a stop! It only takes a few minutes.
• Stonewall Kitchen Flagship Store & Café  – This New England brand started in Maine, and is now sold in specialty stores all over the country, but the flagship store has everything, and is really fun! The café is also very good, and a lot of people come here for lunch.
• Downtown York  – Waterfront scenery, and some cute shops.
• The York Cliff Walk  – A pedestrian path along the coast with beautiful views.

*If you’re short on time , I would just do Nubble Lighthouse and maybe Stonewall Kitchen, but if you have time, I do recommend the other two stops.

Marginal Way in Ogunquit, Maine.

Best Things To See In Ogunquit In A Day :

→  The charming downtown  is filled with shops and eateries.

→  Ogunquit Beach , which is one of the best beaches in Maine!

→  Marginal Way , which is a pedestrian walking path along the coastline that connects downtown Ogunquit with the cute Perkins Cove Harbor.  This is my personal favorite thing to do in Ogunquit.  The trail is easily accessible from downtown, and is just over 1 mile long each way.

→  Perkins Cove  – Once you arrive there after walking Marginal Way, there are some really cute shops to explore, and a lovely bridge that makes for fun photos.

Ogunquit Beach Lobster House Restaurant.

Where To Eat In Ogunquit :

• Ogunquit Beach Lobster House
• Footbridge Lobster in Perkins Cove for a lobster roll!
• BeachFire Bar & Grille

Psst!  I have an entire guide on  things to do in Ogunquit , if you’re looking for more ideas!

Kennebunkport, Maine.

Best Things To See In Kennebunkport In A Day :

→  The adorable downtown , which is mainly Dock Square. You’ll find colorful storefronts and great restaurants here.

→  Drive to Cape Porpoise , where you’ll find beautiful coastal New England scenery, and the cute  Farm + Table shop .

→ Enjoy the views of the cove from  Kennebunkport Bridge  (right at Dock Square).

→ Take a coastal walk on  Parsons Way .

→ If you have time, head out on a  lobster tour with Rugosa .

Where To Eat In Kennebunkport :

• Allison’s Restaurant for a great casual meal
• Cape Porpoise Lobster Co. for a lobster roll!
• Old Vines Wine Bar

Day 3: Drive To Portland & Make Your Way To Camden

Portland Head Lighthouse.

This day ends in the beautiful coastal town of Camden, but you’ll be making some fun stops along the way! You can make this day easy by just driving to Portland, and then driving straight to Camden, or you can make it longer and more adventurous by making as many stops you as you feel like. Take a look at all my suggestions, and plan according to your preferences 😊

Option to add a night in Portland : The reason I have you scheduled to only stop in Portland for the day is because it’s  such  a short drive from Kennebunkport and Ogunquit, and personally, I think the scenery around the Camden area is more quintessential Maine. However, if you have extra time, you can definitely stay the night in Portland, and continue on to Camden the next day!

Things To Do In Portland In A Few Hours:

→  Take a food tour!  Portland is a huge foodie destination, and this is a great way to taste your way through the city.  The Old Port Seafood Lovers Tour , and  Old Port Culinary Walking Tour  are both great options.

→  Visit the lighthouses.  If you only have time for one, definitely make it  Portland Head Lighthouse . This is probably the most iconic lighthouse in New England, and it’s absolutely beautiful. Nearby are also  Spring Point Ledge Light , and  Bug Light , which are smaller, but still fun to visit. These are all in South Portland, so you’ll want to see them first before getting to downtown Portland.

Old Port in Portland.

→  Stroll around Old Port . I suggest parking somewhere around Commercial Street, and then walking around from there. This is the most unique and charming part of the city along the waterfront. Exchange Street and the streets nearby are nice shopping areas, too.

Optional Stops That Are Worth Your Time On The Way To Camden :

Some of these will definitely add time to your trip, so map them out carefully based on your plans to ensure you have enough time in your day.

Marshall Point Lighthouse.

→  Freeport  to shop at the L.L. Bean Flagship Campus.

→  Wiscasset  – a charming little town with a famous seafood stand called Reds Eats. Also known as being the prettiest village in Maine. You’ll drive right through it on your way to Camden.

→  Pemaquid Lighthouse  – a beautiful lighthouse surrounded by dramatic coastline and parks. There is a small fee to enter the grounds, and it’s cash only.

→  Moody’s Diner in Waldsboro  is right on your way on the righthand side, making it  a little too easy  to swing in for one of their famous whoopie pies! It even made my list of the  best whoopie pies in Maine .

→  Marshall Point Lighthouse  in Port Clyde. This famous lighthouse was featured in the movie  Forrest Gump , and it’s such a beautiful area to visit. This is the lighthouse in my homepage photo!

→  Owls Head  is a small town that’s not too far of a detour, and is home to Owls Head Lighthouse, and some beautiful coastal scenery. This is one of my top, most favorite lighthouses in New England.

→  Rockland  is a charming little coastal town with a great Main Street for shopping. Also home to Rockland Breakwater Lighthouse.

Note s:  You’ll pass by Boothbay Harbor on this portion of the drive, but don’t worry! You’ll be stopping there for a night on the way back  😉  You can also make some of these stops on Day 6 of this itinerary when you drive from Bar Harbor to Boothbay Harbor .

You’ll want to arrive in Camden around dinnertime, so you can get settled into your hotel, and then explore the town a bit before sunset.

Camden, Maine.

Best Things To Do In Camden:

→  Head out on a sunset windjammer tour!

→  Walk around the harbor  to enjoy the idyllic waterfront scenery. Also walk over to the Bay Road Overlook (comes up in Google Maps) for the perfect view of the harbor backdropped by the mountains.

→  Grab dinner at a fabulous restaurant . Some of my favorites are Natalie’s, The Waterfront (yep, that’s the name 😊), and Franny’s Bistro.

→  Get some ice cream for dessert  at River Ducks or Camden Cone.

→  Drive the auto road  in  Camden Hills State Park  to the top of Mt. Battie and enjoy the bird’s-eye views of the harbor. This road is only open seasonally, but usually only closed in the winter.

→  Shop the lovely boutiques  on Main Street and Bay View.

Day 4: Spend The Morning In Camden & Then Drive To Bar Harbor

Refer to the section above for ideas on things to do in Camden the next day. If you weren’t able to take a sailing tour the night before, I do highly suggest booking one for the next day before you leave – this is one of the best places in Maine for a sailing tour!

⛵︎ Here is the Camden sailing tour I recommend:

Windjammer Classic Day Sail

Then, make the drive directly to Bar Harbor. On the way, you’ll cross the  Penobscot Narrows Bridge , which is one of only four bridge observatories in the entire world! If you have time, it’s worth a stop to enjoy the views from the observatory.  Click here for information and fees for exploring the bridge . But it is completely free to drive over if you’re just passing by.

Things To Do Your First Night In Bar Harbor:

→  Walk around the adorable town .

→  Enjoy sunset from Shore Path right in town , with is a coastal walkway.

→  Grab dinner out . I love Geddy’s, Side Street Café, and the Happy Clam Shack for lobster rolls if you’re up for a short drive outside of town.

→ If you have the time, you could also drive up Cadillac Mountain for sunset. While it’s famous for sunrise, I also love sunset on a clear night and it’s usually less crowded.  Note that this requires advanced planning and reservations late May – October.

Sunset on top of Cadillac Mountain.

Day 5: Explore Acadia National Park

Today’s THE day – Acadia National Park! Known as the “Crown Jewel” of New England, the park spans over 70 acres on Mount Desert Island, and offers some of the most iconic and famous scenery in the region.

Best Things To Do In One Day In Acadia :

→  Start with sunrise at the top of Cadillac Mountain . You can also save this for the following morning.Depending on the time of year, you may have to wake up very early for this, so it’s definitely not for everyone. But if it works with your schedule, I do think it’s worth it. It’s one of the most popular activities in the park for a reason!

Note :  Reservations are required late May – October to drive the auto road to the Cadillac Mountain summit . They release 30% of the available reservations 90 days in advance, and 70% of them two days in advance. I recommend setting yourself a reminder to check the weather two days in advance, and if it’s forecasted to be a clear day, making the reservation if this interests you. That way, it’s worth it! If it’s forecasted to be cloudy and foggy, the views won’t be a great.  Click here for reservation info .

→  Drive Park Loop Road , which is one of the most scenic roads in the park that offers so much for little effort. Along this road, you can make stops at Sand Beach, walk the Ocean Path, visit Thunder Hole, and see the Otter Cliffs. Of all these, I recommend parking at Sand Beach and walking Ocean Path to Otter Cliffs and back. It’s flat and easy, and passes by the best views in the park!

→  Lunch at Jordan Pond House . Famous for their popovers and incredible views overlooking Jordan Pond, this is such a fun thing to do in the park. If the weather is forecasted to be nice, I recommend making reservations for outside if you can. They also have a take out café if you want a quicker experience.

This overlook of Monument Beach is along the Ocean Path trail in Acadia.

→  Take a hike, of course!  Some easier to moderate hikes in the park that I love are Great Head, Bubble Rock, and Gorham. If you’re looking for an adventurous hike that’s more challenging, Beehive is the most popular in the park. Great Head is especially nice because you start the trail at Sand Beach, and it offers spectacular views of the coastline. And then you can just leave you car in the parking lot and walk Ocean Path.

→  Head to Bass Harbor Lighthouse for sunset . It’s about 30 minutes from Bar Harbor, but on a nice night, sunset here is really beautiful. You’ll need to climb out onto the coastal rocks to see the lighthouse, and parking fills up fast. But if you come prepared with sturdy footwear and arrive early enough, it’s wonderful!

→ If you don’t feel like driving to Bass Harbor Light, I would head back to Bar Harbor to  relax and enjoy your last night in town  with a dinner out.

→ You can also try to make a reservation for  sunset on top of Cadillac Mountain  in the park if you weren’t able to go for sunrise!

The views at the top of Cadillac Mountain.

Psst!  Do you have longer to explore the park? Want more information on everything mentioned above? You may want to check out my  Perfect Acadia National Park Itinerary .

Day 6: Drive To Boothbay Harbor

You have the option to start your day with a sunrise on Cadillac Mountain if you weren’t able to plan it the day prior! If you do, I suggest having breakfast at  Jeannie’s Great Maine Breakfast  in Bar Harbor afterward before heading out. They usually open early in-season for everyone getting up to see the sunrise ☀️

The drive to Boothbay Harbor is about 2 hours and 45 minutes without stops, and you also have the option to take the more scenic route and visit some of the suggested stops I detailed in the Day 3 portion of this itinerary. I would go back and reference those if you want to break up the drive.

Why do I recommend the night in Boothbay Harbor?  Well, I just love this little coastal town because of its charm, beautiful scenery, slower pace, and all the amazing boat tour options. From Boothbay Harbor, you can take a boat tour out to a puffin colony, head out on a Schooner, or take a lobster trap haul and lighthouse scenic tour. After exploring Acadia the day prior, it’s nice to stop in a town that forces you to slow down a bit, too.

Boothbay Harbor.

Best Things To Do In Boothbay Harbor:

→  Take a boat tour!  In addition to Camden, this is another one of the best places in Maine for some kind of tour out on the water just because of how many different kinds are offered. Plus, the scenery around this area is absolutely beautiful.

The Lobster Haul, Lighthouses & Seals tour in Boothbay Harbor.

These are the top tours I recommend in Boothbay Harbor:

✓  Schooner Day Sail

✓  Schooner Sunset Sail

✓  Lobster Haul, Lighthouses & Seals Tour

→  Cabbage Island Clambakes!  This is SUCH a cool, unique, and authentic Maine experience for dinner. You’ll take a boat from downtown, and be brought to the family’s private island for a traditional New England style clam bake dinner, which includes their famous blueberry cake and gorgeous waterfront scenery.  Advanced reservations required.

→  Coastal Maine Botanical Gardens . Located just outside of the downtown area, this is such a beautiful place to explore. Don’t forget to snap your photo with the giant wood troll sculptures!

→  Explore the cute and colorful downtown area .

→  Walk the footbridge , which connects both sides of the harbor.

→  Grab ice cream from Downeast Ice Cream , which is one of my favorites in New England.

Downtown Boothbay Harbor.

Where To Eat In Boothbay Harbor :

• Boathouse Bistro
• Boothbay Lobster Wharf
• Shannon’s Unshelled
• Robinson’s Wharf in the neighboring town of Southport is also worth it!

Psst!  I have a post all about  things to do in Boothbay Harbor , if you want some more ideas 😉

Day 7: Drive To Portsmouth & The Essex Coastal Scenic Byway

Portsmouth, New Hampshire.

Making your way back to Boston, there are so many wonderful places you can stop on the way! In fact, it’ll be hard to choose because there’s a lot you can pack in on this portion of the drive, especially along the Essex Coastal Scenic Byway in Massachusetts.

Customize this day how you’d like, but if you’re feeling ambitious and you have enough daylight hours in your day, you can see Portsmouth,  and  all the best towns in the along the Scenic Byway.

Things To Do In Portsmouth In A Few Hours :

Portsmouth is very walkable and compact, so you can see the highlights, even with just an hour or two!

→  Market Square , which is the main shopping area downtown. You’ll find lots of great boutiques and eateries in this section of town.

→  Walk down a cute alleyway to Elephantine Bakery  for a coffee and a sweet treat.

→  Walk over to Prescott Park  for lovely waterfront views and a garden.

→  Visit the   Strawbery Banke Museum  to see history come to life (open seasonally). If you don’t go to the museum, definitely walk around this area because you’ll see lots of historic houses nearby.

Once you’re done in Portsmouth, take a 30 minute drive to Newburyport  and explore there for a bit. This is where I recommend starting the Coastal Byway drive. Follow the Byway through Ipswich, Rockport, Glouster, Manchester By The Sea, and Salem (which is just outside of Boston).

These are the best stops to make along the Essex Coastal Scenic Byway:

→  Newburyport : One of my favorite places to visit in New England, it’s home to amazing shops and such a charming downtown area that sits on the waterfront. Allow about an hour to walk around, grab lattes and whoopie pies from Chococoa Café, and explore the shops.

Psst!  I have an entire guide on  things to do in Newburyport, MA & Plum Island  if you need more info!

Newburyport, Massachusetts.

→  Crane Estate & Crane Beach in Ipswich . This historic estate is so stunningly beautiful, and the beach nearby is the best on the North Shore. Each requires separate admission fees, and you’ll want to budget your time wisely.

Crane Beach in Ipswich.

→  Rockport : One of my all-time favorite coastal towns in New England, Rockport is probably the one place I recommend you don’t miss on the drive. It’s very small, but offers an authentic New England fishing village atmosphere with colorful storefronts, lovely art galleries, great dining, and the most painted building in the country – Motif 1 (which was also featured in the movie  The Proposal ).

Psst!  I have an entire guide on  things to do in Rockport, MA  if you need more ideas!

Rockport, MA.

→  Gloucester is the best place to stop if you have your heart set on a whale watch tour  (but you can also take one that departs from Newburyport if that’s more convenient). Whale watch tours in this region are world-class, and head out to the famous Stellwagen Bank National Marine Sanctuary, which is known for its active marine wildlife.

🐋  Click here to check rates & availability for a whale watch tour from Gloucester

Note : While I do love to visit Gloucester, I think with this amount of time, it’s best to focus your itinerary on the other towns along the drive that I’ve recommended, as I think their scenery is more idyllic than Gloucester. Gloucester is also a city, and is bigger and more spread out, so harder to see on limited time. I do recommend it for a whale watch tour, though! If you take the whale watch tour, just know that it will take at least 3 hours, and likely a bit longer.

→  Manchester-By-The-Sea  is a beautiful coastal town that can easily be seen in about an hour or so. very picturesque scenery, and it’s home to a lovely beach called Singing Sands.

→  Salem . I’m sure you know it as a top Halloween destination, but it’s honestly great year-round. Filled with historic New England charm, waterfront areas, and some fun places to eat, it’s also very walkable!

Psst!  I have an entire guide on taking a  Salem, MA day trip  if you want more information for your visit!

Marblehead, Massachusetts.

→  Marblehead  is such a beautiful town along the North Shore just south of Salem that often gets overlooked, but I absolutely love it here. Also filled with historic charm and lovely waterfront scenery, it’s got a quaint Main Street with some cute shops, a beautiful waterfront park, and some nice places to eat.

Psst!  I have an entire guide on  things to do in Marblehead, MA  if you’re looking for more ideas 😉

More Optional Stops : If you’re looking to explore more of Maine’s coast, there are a few more stops you can make on your way from Boothbay Harbor to Boston. I know, I know – I’m probably tempting you to expand your trip even further, but I’m okay with that 😂

→  Georgetown Island to visit Five Island Lobster Company , which is one of the best lobster rolls in Maine you can get. They’re only open seasonally, and the scenery around there it is very quintessential Maine.

Doubling Point Lighthouse.

Squirrel Point Lighthouse.

→  The Arrowsic Lighthouses . There are two in this area that I really love: Doubling Point and Squirrel Point. Doubling Point requires a drive down a very bumpy dirt road, and Squirrel Point requires about a 3/4 mile hike through the woods, but they’re both beautiful, small lighthouses on the Kennebec River.

Note :  Doubling Point is closed until further notice for repairs. I’m monitoring this and will update once renovations are complete!

→  Bailey Island , which is a very small little island that’s accessible by car, and about a 20-minute detour each way. The best thing to see here is the Giant’s Stairs Trail, which offers beautiful coastal views, and giant rocks you can climb around (just practice caution, of course!). There’s also a cute little place to eat right by the bridge called Sundrenched, which is waterfront and has outdoor seating. This is a nice place to get off-the-beaten-path.

Giant’s Stairs on Bailey Island.

Day 8: Head Back To Boston

It’s the end of your trip! Depending on when you need to make your way back home, or to the airport, you may have some time in the morning to explore a few of the places I mentioned above, but I left this day open in case you have to catch an early flight, or start your drive back home early.

If you do happen to have some time on this day to explore, I would suggest you end the previous day in Rockport, and then explore Salem and Marblehead on this day before heading back to the airport.

Optional Itinerary Adjustments

→ If you have more time and are a city person, I would recommend adding a night to Portland and Boston.

→ If you have extra time and don’t want to add a night to a city, I have two suggestions.  First option : add a night to Camden to spend a day exploring the nearby attractions (lighthouses, Rockland, etc.) to make the drive from Portland to Camden easier.  Second option : add a night to Bar Harbor to see more of the park, and enjoy more hiking.

→ If you have even longer, you could make this a 2-week adventure by driving up the coast of Maine to Lubec, and then crossing the Canada border to the charming town of St. Andrews by the Sea, and Campobello Island. You could also take the CAT ferry from Bar Harbor to Nova Scotia.

I have a detailed guide on  visiting Lubec, Maine , if you wanted to explore places further north!

Best Towns To Stay In On The Drive

For an overnight stay, these are my suggestions on the best places to stay based on experience when it comes to options for dining and accommodations (plus, lovely scenery, of course!). You’ll just want to pick where you stay based on how far you want to drive each day.

As you saw in my itinerary, I included some suggestions for overnight stops, but you may want to customize this trip to your liking (which I encourage!), so I wanted to provide you with more options. It’s also good to know that you won’t have time to stay overnight in all these places unless you extend your trip, but you  will  be able to, at the very least, drive through them all.

→  Rockport, MA : Not far from Boston, and if you’re looking get a leisurely start or slow-burn end to your trip, I really love to recommend a stay in Rockport. Most everything is pretty walkable, with cool shopping, nice hotel options, and idyllic scenery.

Where To Stay In Rockport :

✓  The Cove at Rockport

✓  Addison Choate Boutique Hotel

→  Portsmouth, NH : As mentioned, fantastic dining and shopping, with lots to keep you busy in the evening after you arrive! Plus, the historic charm is really quite lovely.

Where To Stay In Portsmouth :

✓  The Hotel Portsmouth

✓  Hotel Thaxter

→  Kennebunkport OR Ogunquit : Both of these charming coastal towns that are very close to on another, and both make for a great overnight stay. Kennebunkport has more options for nicer accommodations, but Ogunquit has a gorgeous beach. Both have very charming downtowns that are easily walkable with lots of places to eat and shop! Just pick based on what vibe you’re going for: beachy or just traditional coastal.

Where To Stay In Kennebunkport :

✓  Captains Collection Historic Inns

✓  The Boathouse

Where To Stay In Ogunquit :

✓  Anchorage By The Sea

✓  Cliff House : Technically in York, but a short 10-minute drive to Ogunquit. I like to suggest it because it’s a fantastic resort with amazing coastal views, and worth the splurge! It also makes my list of the top  New England resorts and spas  😉

→  Boothbay Harbor : I love stopping here for a night or two every time I make this drive. It’s very small and easily seen in a few hours, and I like to stay the night so I have the option to take a boat tour. I also find the shops and restaurants really great.

Where To Stay In Boothbay Harbor :

✓  Harborage Inn On The Waterfront

✓  Spruce Point Inn

→  Camden : Lastly, I think Camden is the best place to stay before reaching Bar Harbor. Built around a gorgeous harbor, the coastal scenery here is beautiful, and it’s a known sailing destination. There’s also a great Main Street for shopping and dining.

Where To Stay In Camden :

✓  Camden Harbour Inn

✓  Lord Camden Inn

Where To See Fall Foliage Between Boston & Bar Harbor

Manchester By The Sea in the fall season.

If you happen to be planning your trip to coincide with fall foliage, then I would love for you to consider adjusting the itinerary slightly (but don’t worry, it’s not too different!). Most places already on the itinerary offer amazing foliage color. Here are some suggestions to keep in mind:

→  The Essex Coastal Byway in Massachusetts is GORGEOUS in the fall  with lots of foliage color. I’ve done this drive during peak foliage, and I was shocked at how beautiful it was. Manchester-By-The-Sea, Essex, Salem, and Newburyport are especially beautiful in the fall. And, of course, Salem is  famous  for its October festivities!

→  Portsmouth offers some really lovely fall foliage  during this time of the year. It’s also an especially cozy place to visit because of all the historic New England architecture.

→  Boothbay Harbor  is also amazing in the fall, and the entire harbor is surrounded in fall color. Head out on a boat tour to see even more beautiful fall foliage! Tours usually end around mid-October, so there are typically opportunities that coincide with peak foliage.

→  Camden is also spectacular in the fall . I definitely recommend hiking or driving up the Mt. Battie Auto Road to take in the views of the harbor from above. It’s the best during foliage season!

→  Kennebunkport  also offers some beautiful fall foliage. Having been in October a few times, the fall season always impresses me in this coastal town.

Kennebunkport, Maine in October.

→ Of course,  the starting and end points on this road trip are stand-outs in the fall, too.   Acadia National Park  is stunning in the fall season with foliage color, and  Boston  is also amazing this time of the year. Although, it’s good to know that Boston tends to peak later in October, so in the fall, you may want to plan to spend more time in Boston at the end of your trip to get a glimpse of some foliage color.

What To Pack For This Road Trip

This will depend entirely on what time of year you visit, so plan accordingly based on the season when it comes to clothing and footwear. Beyond that, here are some things I recommend you bring regardless of what time of year you visit.

→  Light sweater or jacket  – even in the summer! If you plan to take any boat tours or get up for sunrise at Cadillac Mountain, you’ll want this to stay warm.

→  Reusable water bottle  to stay hydrated.

→  Dramamine  if you plan to hop on a boat tour and tend to get seasick.

→  Comfortable shoes  – I know this seems obvious, but you can leave your fancy shoes at home. I usually wear a really comfortable pair of sandals in the summer, or sneakers in the spring/fall. If you take a boat tour, they may have some requirements on the type of footwear you wear, so double check that, too.

→  Hiking boots  if you plan to tackle any trails in Acadia. You’ll be happy to have the ankle support.

→  Camera, of course!  You’re going to see so much incredible scenery on this trip, you’ll want to capture the best memories along the way. This is a good trip to get a tripod if you don’t have one – they even make inexpensive ones for iPhones that are perfect for just about anyone.

Tips For This Road Trip

→  Offline maps  on your GPS! You’ll have cell phone service in most places, but when you’re near a beach or inside Acadia National Park, you may lose service.

→  Be ready to pay tolls on the roads . If you’re renting a car for the trip, I suggest making sure your rental comes with an EZ Pass for the toll roads to make things easier. Most of them in this area are now cashless and don’t require you to stop – you just get a bill for the tolls instead, which you can work out with your rental company.

→  Bring Some Cash  – I know this seems obvious, but as someone who  never  carries around cash, I’m always reminded when I make this road trip that some places still don’t take credit cards! Usually places like ice cream stands and seafood shacks are the ones that may be cash only, so it’s good to have a small amount on you at all times. Better yet, get a debit card that reimburses you for ATM fees, like the Charles Schwab checking card. Most places will take cards, though.

→  Prepare for crowds at popular places . Depending on the time of year you take this trip, most places will bring in some level of crowds. The most popular destination is Bar Harbor and Acadia National Park, and this is where you can expect the biggest crowds. If you travel in spring or fall, you’ll see fewer people, but places will still be lively.

→  Prepare for the cost . New England in general is just an expensive region to visit, unfortunately, and prices tend to be higher than other parts of the country.

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That’s A Wrap On The Boston To Bar Harbor, Maine Road Trip!

And there you have it! After years of perfecting it, I’m thrilled to finally share my unforgettable Boston to Bar Harbor, Maine road trip itinerary with you. I truly believe that the New England coast is such a special and memorable region to experience for yourself, and with this guide, you’ll see the very best it has to offer. Happy planning!