13+ Unforgettable Road Trips from Boston to Take This Year

Boston, a charming Northeast city, is best known for its role in American history. While there are plenty of things to do in Boston on its own, there are also so many surrounding cities and parks that are only a quick road trip from Boston that are also worth exploring!

Having grown up in California, I was not used to the accessibility of other states until living on the east coast! It’s as easy as hopping in your car, and you could be in another state or city near Boston exploring a state park, a beach, or a wine region!

With the help of my fellow travel bloggers, we have crafted a list of the best road trips from Boston that I encourage YOU to take this year!

So, let’s get into it!

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Map of the Road Trips from Boston Destinations

Here is a map showing all of the destinations that this list of the best road trips from Boston includes!

The Best Road Trips from Boston

On this list, you will find some road trips that will take you under an hour, and some that might even need to be broken up into multiple days! We’ve included the road trip length and distance to allow you to better plan your journey.

1. Boston to Mystic, CT

Recommended by Kitty from Kittymeetsworld

Driving to Mystic, Connecticut makes for an excellent road trip from Boston. The drive itself will take around two hours (and in fall offers a chance to admire autumn colors).

If you want to break up your journey, you could stop in Providence, RI, to check out the beautiful campus of Brown University and the downtown area. Closer to Mystic, Saltwater Farm Vineyard on the Connecticut Wine Trail would also make for a fun stop.

But, the highlight of this road trip is the destination. Mystic is the prototype of a traditional coastal New England town. With its clapboard houses, white church, tree-lined streets, and quaint stores, the historic downtown of Mystic is ideal for a stroll. If you time it right, you may even see the bridge being raised to let sailboats pass through!

Don’t miss out on a visit to Mystic Pizza, made famous by the 1988 film with Julia Roberts. If you would rather enjoy seafood in a casual atmosphere, nearby Noank has two popular lobster eateries. Watch out for seagulls though if sitting outside – they will steal your food if you are not careful!

Aside of the charming village that seems to be straight out of a Norman Rockwell painting, Mystic boasts another major attraction: Mystic Seaport. Seaport Village recreates life in a whale fishing village in the 1880s and is a must-see on your road trip.

In the summer and on weekends, docents in period clothing show traditional craft, fishing, and farming methods. In addition, you can explore historic boats and even take a ride on a steamboat.

2. Boston to the Berkshires, MA

Recommended by Karen of Outdoor Adventure Sampler

The Berkshires in Western Massachusetts are an ideal road trip from Boston. Located a mere two hour drive from Boston, the vacation paradise of the Berkshire mountains is a spectacular place to explore. Take the Mass Turnpike for 125 miles to the western part of the state to access the many small towns.

Visitors are drawn to the outdoor beauty of the Berkshires in all seasons. Outstanding fall foliage is a showcase for travelers from all over the world. In the winter, the Berkshires become a snowy wonderland. Cross country, snowshoeing, and downhill skiing areas can be found throughout the Berkshires.

However, summer may be the most popular season to visit the Berkshires. Charming villages with boutique shops and farm to table restaurants abound. 

Besides outdoor activities, the Berkshires area is home to the Norman Rockwell Museum, the Clark Museum, and the innovative Massachusetts Museum of Contemporary Art (MassMOCA). The Berkshires also boasts the open air music venue Tanglewood. It has an immaculate lawn for spreading out a picnic while watching world-class concerts. The summer home of the Boston Symphony Orchestra is also at Tanglewood.

I enjoy spending a few days in the Berkshires to see some of the natural beauty such as Bash Bish Falls. It’s also easy to immerse in the culture and spend a few hours exploring the museums and historic towns. End the day with a stay in one of the classic New England inns with stone fireplaces and historic touches.

3. Boston to Chatham, MA

Recommended by Fab 5 Family Travel

Chatham is one of the most beautiful destinations on the Cape, and recently was able to take this road trip with my husband on summer vacation! We flew into Boston and left directly from the airport. We arrived mid-morning, so didn’t experience much traffic but keep in mind the traffic worsens on Fridays and on the weekends as people flee the city for the Cape beaches.

We loved our stay at the Greyfinch Inn and our time exploring Chatham. Some of the best things we did were stroll through the charming downtown, see the seals at the Chatham Fish Pier, eat fresh seafood, and visit the iconic lighthouse.

Chatham’s beaches are gorgeous and a great way to unwind. If visiting in the summer, make sure to secure a parking pass for the popular beaches and catch a baseball game in the Cape Cod Summer League. 

While in Chatham, you must go to the Cape Cod National Seashore that stretches throughout the Cape. It was a highlight of our trip. If you love history, learn about the region’s history at Chatham Marconi Maritime Center or the Atwood House Chatham Historical Society.

4. Boston to Martha’s Vineyard, MA

Recommended by Maria from Martha’s Vineyard Travel Tips

Martha’s Vineyard is the perfect destination for a road trip from Boston. If you time it just right, you can be sitting on the beach, basking in the sun less than 3 hours after leaving home. 

Some of my favorite things to do are to take a stroll around the colorful gingerbread cottages in Oak Bluffs or visit Edgartown Lighthouse. If you really want to get away from it all, I recommend hopping on the Chappy ferry and visiting the secluded, pristine beaches of Chappaquiddick.

When you arrive on Martha’s Vineyard, you’ll find a charming island full of fascinating history, quaint shops, boutique inns and incredible local seafood restaurants. 

I’ve done this road trip several times and I recommend hitting the road early. Even though the journey is less than 80 miles, if you hit that Cape Cod traffic on a summer weekend, your driving time can double! It’s also essential to make a car reservation well in advance of your trip.

5. Boston to Salem, MA

Recommended by Mackenzie Jervis, A Wandering Scribbler

Heading out on a road trip through Massachusetts to Salem, MA, is not just a journey through miles but a voyage through time, history, and mystique. Salem, with its enigmatic past as the site of the infamous witch trials of 1692, has an intriguing blend of the eerie and the enchanting.

The road trip from Boston to Salem is only about 25 miles, offering a scenic drive through the charming New England landscape. Along the way, travelers can pause to explore historic landmarks such as Marblehead, known for its colonial architecture and maritime heritage.

In Salem, the cobblestone streets feel like stepping back in time. Attractions like the Salem Witch Museum and the House of the Seven Gables, where Nathaniel Hawthorne found inspiration for his novel of the same name, are great places to explore. While Salem is worth a visit any time of the year, the city truly comes alive in the fall. Salem’s Halloween festivities, held each October, are like a giant party throughout the town for those who love witches, spooky activities, and the history of the witch trials.

Salem also has a lively arts scene, with galleries, boutiques, and artisan shops lining its streets, offering a modern contrast to its historical significance. Salem’s food scene offers fresh seafood and locally sourced fare, while its waterfront promenade provides a serene backdrop for relaxation. Whether drawn by history, culture, or simply the allure of the unknown, a road trip to Salem from Boston promises an unforgettable adventure steeped in mystique and charm.

6. Boston to Ocean City, MD

Recommended by Denise from Chef Denise

A road trip to Maryland is a perfect way to spend a summer weekend! I’ve done this road trip from Boston to Ocean City many times, and it can easily be done in a day. However, I prefer to make some stops along the way as this route goes through two of America’s most amazing cities: New York City and Philadelphia. It’s even more worth it if you can spend a night in each. 

You can drive to Manhattan in about 4 hours from Boston. I like to leave early so I can have lunch in the city and take a long walk down 5th avenue and through central park. Then I have an amazing dinner, preferably where the view of the Brooklyn Bridge rivals the food.

From NYC to Philadelphia, it’s less than two hours. So I load up on a big breakfast at Veselka in the East Village before hitting the road. As a big foodie, in Philadelphia I’m happy wondering around Reading Market all day and landing where my taste bud take me. With a good dose of historical sights mixed in, of course. 

Then, it’s just 2.5 hours to Ocean City. Summer is the best time to visit Ocean City because as the name implies, this is a resort town that comes alive from Memorial Day through Labor Day. With a seven mile boardwalk, a warm Atlantic Ocean, and lots of water activities, the beach is where you’ll want to be. It’s also where you’ll find the best crab restaurants in Ocean City—the real reason to visit in summer—crab season!

7. Boston to Acadia National Park, ME

Recommended by Melody Fanslau from The Winding Road Tripper blog

A road trip to Acadia National Park is full of quaint towns and beaches, so it will be jam-packed with options for you to create your own trip depending on the amount of time you have.

One of the best parts about this road trip is it takes you along quiet highways along the coast (Highway 1 and 1A) and avoids Interstate 95.  

The best stops along this route include Salem, MA, Portsmouth, NH, Portland, ME, Camden, ME, and Bar Harbor/Acadia National Park, ME.

Salem hooked me with its eerie past and quirky museums. It was like walking through history with a spooky twist. Then, Portsmouth was a breath of fresh air—historic yet lively. Cafes, shops, and that old-world charm made it the perfect pit stop.

Maine was a showstopper with its scenic beaches and quaint towns. Portland was a blend of city cool and seaside charm. I had some of my favorite cocktails at Blyth & Burrows. The Portland Head Light was postcard-perfect, and wandering the Old Port was a day well spent.

Maine has many great coastal towns, but Camden was one of my favorites. You can spend time hiking in Camden Hills State Park or take a sunset sail. 

As for Acadia National Park, it was the grand finale. From the stunning views on Cadillac Mountain to the serene beauty of Jordan Pond, it was nature at its best.

This road trip was more than just a drive; it was a collection of awesome stops, breathtaking views, and delicious eats. Each stop had its unique flair, making the journey unforgettable.

8. Boston to Portsmouth, NH

Recommended by Stacy from Explore Baja California

Portsmouth is a historic city in that boasts a well-preserved downtown area with cobblestone streets, brick sidewalks, and elegant colonial architecture that is perfect for a weekend getaway from Boston.

If you don’t have a car, there are also bus services available between Boston and Portsmouth. Companies like Greyhound, C&J Bus Lines, and Concord Coach Lines operate several buses per day between these two cities. 

June to August is the peak season in Portsmouth. The weather is warm, and there are numerous outdoor activities and you can enjoy outdoor festivals, concerts, and dining. The downside is that it can get crowded, and accommodation prices may be higher during this time. 

September to November is fall foliage season in New England, including Portsmouth, which is renowned for its stunning colors. I visited Portsmouth in September and had a great time, as it was still sunny and pleasant to be around.  

The weather is generally pleasant throughout September and the first half of October, and there are still plenty of outdoor activities to enjoy, such as hiking and leaf-peeping. And, it is the visit fall-themed events and enjoy seasonal treats like apple cider and pumpkin-flavored treats at local farms and stores!

9. Boston to White Mountains, NH

Recommended by Sophie from Delightful Travel Notes blog

A road trip from Boston to the White Mountains promises a mix of natural beauty, adventure, relaxation, and family fun. As you approach the White Mountains, the view transforms into a breathtaking vista with rugged mountain peaks, dense forests, and crystal-clear streams.

The best time to take this road trip is in the fall. Fall is a highly popular time to visit due to the spectacular fall foliage. The weather is also pleasant for hiking and outdoor activities.

Summer months are also perfect for those interested in hiking, camping, and other outdoor activities. The weather is warm, and all attractions and trails are open, including mountain coasters and water parks.

The area has a wide range of activities year-round but it is extremely beautiful in the fall. The forests become a vivid palette of reds, oranges, yellows, and golds. When visiting this region, we like to stay in North Conway, which is very convenient to access attractions and scenic drives, especially the famous Kancamagus Highway.

Due to its popularity, it is important to plan ahead if you want to see fall colors in the White Mountains. Accommodations can fill up quickly, and some areas may experience heavy traffic, especially on weekends.

10. Boston to Montauk, NY

Recommended by Samantha Oppenheimer of Find Love and Travel

I couldn’t recommend a better road trip from Boston than a trip to Montauk. You will find this wonderful beach town located at the end of the peninsula of Long Island, New York. Montauk is the perfect location for a spring or summer getaway! 

This is unlike any other locations that you’re probably familiar with in New York as it has a much more serene atmosphere, instead of the bustling streets and city lights. Plus, during your drive from Boston, you’ll get to experience some pretty incredible scenery, too.

The road trip is worth taking because there are so many great attractions to visit while there. Hiking and biking are both some of the best things to do in Long Island, and are very popular since there are six state parks to choose from. The Montauk Lighthouse is a great family-friendly activity. Then, after a day of driving and exploring, you can settle down on one of the beaches to enjoy an incredible sunset. Gin Beach is my favorite! 

11. Boston to New York City, NY

Recommended by Rebecca from Veggies Abroad

A road trip from Boston to NYC offers a scenic journey through picturesque small towns, ending with the Big Apple! If this is your first East Coast road trip adventure, I suggest taking the route via I-95 so you can enjoy a mix of scenery.

This route is especially great in the summer as you will have beautiful weather and longer days, but it’s also beautiful in the fall with the colorful foliage. I would avoid it in the winter, as the East Coast can be pummeled with snow and brutal winter weather. 

As you head to NYC via I-95, consider making two stops, first in Providence, Rhode Island, and second in the quaint town of Mystic, Connecticut.

In Providence, try to plan your trip around one of their unique WaterFire events! Generally, from late spring through fall, the city lights bonfires along the river, and there are activities and live music.

Mystic, Connecticut, is a charming small town known for its maritime museums, but it’s also the setting for one of Julia Roberts’s early movies, Mystic Pizza! The pizzeria that inspired the movie is still in town and serving up slices!

Once you get to NYC, you’re going to want to ditch the car — heads up, parking fees are astronomical! Just about every hotel offers parking, but be sure to check the prices before you book. NYC is one of the best cities in the US to explore. It’s home to endless entertainment, activities, and just about every type of food you can imagine, from greasy pizza to fancy plant-based eateries.

12. Boston to Newport, RI

Recommended by Jenifer of The Evolista

One of the best road trips from Boston is to the mansions of Newport, Rhode Island. The journey is only a few hours, and a step back in time to the Gilded Age. 

The Breakers, built as the summer residence for Cornelius Vanderbilt II, is the most notable of the Newport mansions. Step into 19th-century opulence and see the architectural grandeur of the Breakers. Then take the Cliff Walk, a scenic path with views of the Atlantic Ocean, to see Rosecliff, where many TV shows and movies have been filmed, and the Chinese Tea House at Marble House.

Fort Adams State Park is the largest fortification on the East Coast with cool tunnels and panoramic vistas of Newport Harbor. If you’re lucky, you may be able to see a concert or sailing race while there. 

Check out the shops on historic Thames Street and walk to Bannister’s Wharf for a meal at Clarke Cooke House Restaurant. On one of your days, take a sailing cruise or a ferry for a day trip to Block Island. Once you arrive, rent a bike to tour Block Island’s beaches, lighthouses, and the Great Salt Pond. Have lunch at the Oar and order a mudslide before heading back to Newport. 

On the return trip to Boston, stop in Providence to visit the RISD Design Museum, Roger Williams Park and College Hill. This road trip is best done in 3-4 days and lets you experience a variety of New England bucket list activities.

13. Boston to Providence, RI

Recommended by Tanya Taylor, Travels & Treasures

Whenever I take a trip out of town I try to make the most of it and visit another city that is nearby.  So when I booked a girl’s trip to Boston, Massachusetts I thought it would be great to see Providence, Rhode Island. 

I booked a stay for two nights.  On the way, we enjoyed seeing the change of the colorful leaves during the Fall season.

The town was easy to get to and we only had to be on the road for 1 hour.  We settled into our hotel for the evening and awoke refreshed and ready to explore.

First, we went to Brown University and walked around the campus.  It was particularly interesting to learn that it was one of nine colonial colleges founded before the American Revolution. The downtown area was rather small but quaint.  The area is artsy with lots of boutique stores and unique finds.

My favorite experience was exploring Waterplace Park and Federal Hill.  
Waterplace Park is situated along the Woonasquatucket River with pedestrian paths along the riverwalk.  It’s a great spot for a morning stroll or to grab bites and shop when the outdoor market is open.

Federal Hill is a happening neighborhood where locals hang out as a community.  We stopped at Costantino’s Venda Bar & Ristorante, an old Italian restaurant, and sat outdoors near a fountain while listening to live entertainment.  We were also fortunate to catch the start of the Rhode Island Seafood Festival in India Point Park.

The stay was short, but the road trip inspired me to have more adventures.

14. Boston to Burlington, VT

Recommended by Amy Hartle of New England With Love

Vermont is a destination that calls to so many. Green as can be in the summer and vibrant with foliage in the fall, it’s my personal favorite state in New England. If you’re visiting Boston, it’s not a hop skip and a jump up to Vermont, but heading up and taking a road trip through Vermont is 100% worth it.

This trip can be done in one day if you’re feeling up to it, but I recommend a slower pace. If you take Route 2 straight out of Boston, you’ll pass Lexington and Concord: a must stop for history and literary buffs. Once you’re in Vermont, consider stopping overnight in Brattleboro, a fun hip town that’s a bit off the radar. 

After departing Brattleboro, you’ll cross over the mountains along Route 9, a winding road that is especially beautiful in the autumn. Don’t miss the scenic overlook in Marlboro at Hogback Mountain, which offers a “100-mile view.” Gorgeous. 

If Brattleboro doesn’t appeal, Bennington also has a lot of cool things to do, from art to coffee culture to its iconic Bennington Battle Monument. Leaving Bennington, you’ll drive up Route 7. You’ll follow this all the way to Burlington, with numerous possible sites to check out along the way. 

A couple of my favorites:

• Northshire Bookstore in Manchester: one of New England’s top independent bookstores
• Vermont Cookie Love in Ferrisburgh: incredible cookies, right along your route
• Vermont Cookie Love in Ferrisburgh: incredible cookies, right along your route

Finally, you’ll be in Burlington. This is Vermont’s largest city and there is so much to do, including checking out the dozens of local breweries. Don’t miss views over stunning Lake Champlain either, especially at sunset. 

Conclusion

So now you know what the best road trips from Boston are! These road trips not only have an incredible destination to explore, but also include a beautiful drive (if taken during the right season!)

And, if you are looking for more Northeast cities to explore even after reading this, I’ve got you covered! Philadelphia is one of the best cities in the Northeast, with so many free things to do making it an affordable trip!

While I always recommend exploring a city enough to get a feel for it, Philadelphia is compact enough that you can easily craft a 1 day itinerary to explore much of what the city has to offer!

in it for later