30 Best Road Trips From Boston

Planning a road trip from Boston and don’t know where to go? Check out this post on the 30 best road trips from Boston.

As someone who doesn’t know how to drive yet, I’ve been dying to do a road trip out of Boston for quite some time now. However, until I’m able to get my license, my dream road trip out of Boston will have to wait. So, instead of pouting about as I wait for my license, I’d rather take this time to tell you some of the best road trips you can take out of Boston.

New England Bucket List Series

P.S. This is a post in my New England Bucket List Series. Here is the complete series:

Road Trips: 30 Best Road Trips From Boston

Ice Skating: The Top 7 Places for Free Ice Skating in Boston

Hiking: 20 Best Hikes for Fall Foliage in New England

Fall Foliage: 12 Best Places for Fall Foliage in Boston

Thrift Stores: The 7 Best Thrift Stores in Boston for Vintage

Salem: One Day in Salem Massachusetts: Hocus Pocus Edition

Museums: The Top 8 Free Museums in Boston for College Students

Newport, RI (best road trips from Boston)

A trip to Newport, RI is one of the best road trips you can take out of Boston! The road trip will take about 90 minutes by car and there are a lot of fun things to do!

In fact, according to Pamela, Aquidneck Island is also home to Newport! In the island, you will find a lot of breathtaking sea cliffs around the Cliff Walk. The Cliff Walk is a 3.5 mile walk around the shore that shows off the breathtaking views of the mansions and the area. The Breakers is one of the most famous mansions around the area and it has tours available all year round.

Newport is also most popular during the summer due its wide range of water-based activities. Boats line the water all around Newport, and sailing is a common pastime in the area. However, if you’re visiting during the spring or fall, the nature’s colors will also inspire you!

The Naval War College Museum is also worth checking out if you’re looking to learn more about Newport’s history. Bowen’s Wharf and its neighbor Bannister’s Wharf, are even home to a variety of locally-owned shops and restaurants!

Overall, the elegant blend of history, nature and food is what makes Newport a great road trip to take from Boston.

By: Pamela of Directionally Challenged Traveler

Portland, ME (best road trips from Boston)

A trip to Portland, ME is another great road trip you can take out of Boston! The road trip will take about an hour and 45 minutes to complete and you can do a lot of fun things while you’re there.

In fact, according to Kelly, while the fastest way to get to Portland from Boston is via I-95, this highway can often become inundated with traffic once in a while. Therefore, if you have the time, taking Route 1 along the coast is your best option. Not only will it show you some sweeping views of the Atlantic, but you can also make some stops at some iconic places along the way like Ogunquit, Old Orchard Beach, Kennebunkport, and Cape Elizabeth.

In addition, feel free to make a pit stop at the Holy Donut on your road trip if you need food. You can order a sea salt and chocolate potato doughnut once you’re there as well as some coffee.

By: Kelly of Girl with the Passport

Newburyport, MA (best road trips from Boston)

A trip to Newburyport is another great road trip you can do from Boston! The road trip will take about 45 minutes to complete and you can stop by Salem on the way there too.

In fact, according to Newburyport.com, there’s no shortage of things to do in this city. For example, the Clipper City Rail Trail is a 1.1 mile path that runs from the MBTA all the way to the Merrimack River Shoreline. You can run, walk, or bike on this path as you pass by some popular spots like the Graf Ice Skating Rink or the Cashman Park.

In addition, the Waterfront Park is another popular spot you can go to in Newburyport. It has ample green space that is used for sunbathing, relaxing, and hosting events.

Portsmouth, NH (best road trips from Boston)

Portsmouth, NH is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit the Market Square once you’re there.

In fact, according to Planet Ware, there are a lot of top-rated attractions and things to do in Portsmouth. For example, Prescott Park is a popular attraction that is located along the banks of the Piscataqua River. It has beautiful gardens of perennial flowers as well as a performance space and public docks.

In addition, the Prescott Park Arts Festival is also held at the park. This festival brings in many theater performances each summer as well as music.

Provincetown, MA (best road trips from Boston)

A trip to Provincetown is another great road trip you can take out of Boston! The road trip will take about two hours and a half to complete and you can do a lot of fun things while you’re there.

In fact, according to Vicky, you can take a sand dune tour at Provincetown’s Cape Cod National Seashore Park as well as climb to the top of the Pilgrim Monument for some amazing views.

In addition, there are many different art galleries you can visit in town. The gallery district is located in Provincetown’s East End section and it has Friday night art openings every week.

By: Vicky of Buddy The Traveling Monkey

Westerly, RI (best road trips from Boston)

A trip to Westerly, RI is another great road trip you can take out of Boston! The road trip will take about two hours to complete and you can check out Taylor Swift’s house once you’re there.

In fact, according to Business Insider, Taylor Swift bought the Rhode Island mansion for 17.75 million in 2013. She even paid for the entire mansion in CASH! Imagine that. Taylor Swift is not only wealthy but she’s also not afraid to make a grand gesture.

Since then, the musician is continuing to put her home to good use by hosting A-list parties and events.

Lake Champlain, VT (best road trips from Boston)

A trip to Lake Champlain is another great road trip you can take out of Boston. The road trip will take about five hours to complete and you can visit the Waterfront Park once you’re there.

In fact, according to Inspirock, Lake Champlain also offers a range of different activities for outdoorsy fans as well as an exciting food scene. For example, the Burlington Bike Path is a great path near Lake Champlain where people can ride their bikes along the lake.

Lake Champlain also has a shop called Lake Champlain Chocolates where people can buy chocolate bars, truffles and caramels.

Plymouth, MA (best road trips from Boston)

A trip to Plymouth, MA is another great road trip you can take from Boston! The road trip will take about 40 minutes to complete and you can visit Plymouth Rock once you’re there.

In fact, according to Planet Ware, there are a lot of top-rated attractions and things to do in Plymouth. For example, the National Monument to the Forefathers is a popular tourist attraction that is located along Allerton St in Plymouth. The monument commemorates the founders of the Plymouth colony and it was dedicated in 1889.

In addition, try to see if you can do a Native Plymouth Tour once you’re there. This tour will help you see all that Plymouth has to offer with a Native American perspective.

Rockport, MA (best road trips from Boston)

Rockport, MA is another great road trip you can take from Boston! The road trip will take about an hour to complete and you can snap pictures at Motif #1 once you’re there.

In fact, according to Addison Choate, Rockport has plenty of things to do that are under the radar. For example, just off the coast of Rockport you can visit Thatcher Island, an island known for its shipwrecks and for serving as a home for the mafia hitman turned informant, Joe Barboza.

He was a hitman for the Patriarca crime family during the 1960s and was a resident of the island back in 1967.

York, ME (best road trips from Boston)

A trip to York, ME is another great road trip you can take out of Boston! The road trip will take about an hour to complete and you can visit some other beautiful towns in Maine once you’re there.

In fact, according to Amanda, York has that classic coastal New England charm with its clapboard houses and stark white lighthouse. That stark white lighthouse in particular is called the Nubble Lighthouse.

Built in 1879, it is known to be haunted in York, ME by the ghost ship Isadore that wrecked nearby. If you’re interested in entering the lighthouse on your trip, go at your own risk. The lighthouse is not currently open to the public so it will be difficult.

By Amanda of Hey! East Coast USA

Block Island, RI (best road trips from Boston)

A trip to Block Island is another great road trip you can take out of Boston. The road trip will take about three hours to complete and you can go bike riding, kayaking and parasailing once you’re there.

In fact, according to New England With Love, there are a lot of other things you can do on the island as well. For example, you can check out the views at the Mohegan Bluffs.

The Mohegan Bluffs are large clay cliffs that are located on the south shore of the island. They have views that are undoubtedly the best on the island, as you take in the scenery from the water and the beach.

Acadia National Park, ME (best road trips from Boston)

A trip to Acadia National Park is another great road trip you can take out of Boston! The road trip will take about five hours to complete and you can visit the Park Loop Road once you’re there.

In fact, according to James Ian, when you get to Bar Harbor, the gateway town to Acadia National Park, you can easily spend another few days there or even a week.

The area is known for its prime lobster fishing hub in Maine where you can order fresh seafood right from the water’s edge.

In addition, Acadia National Park is a hiker’s paradise. It has dozens of trails available through the woods that offer incredible views of the surrounding oceans and islands. These trails include but are not limited to the Beehive and the Precipice.

By: James Ian of Parks Collecting 

Charleston, RI (best road trips from Boston)

Charleston, RI is another great road trip you can take out of Boston. The road trip will take about two hours to complete and you can visit the East Beach while you’re there.

In fact, according to Vacation Idea, there are a lot of other things you can do in Charleston as well. For example, Charleston has a top rated tourist attraction called the Fantastic Umbrella Factory.

It is known as a 19th century farmyard shoppers paradise in Charleston where visitors can shop at stores and admire local artwork. These stores include but are not limited to the General Store and the Frills. Local artwork can also be admired in the factory at the Henna Body Art.

Gilford, NH (best road trips from Boston)

Gilford, NH is another great road trip you can take from Boston! The road trip will take about an hour and a half to complete and you can visit the Gunstock Mountain Resort once you’re there.

In fact, according to Vacation Idea, there are a lot of other things you can do in Gilford as well. For example, Gilford has a top rated tourist attraction called the Pepi Herrmann Crystal Gallery and Museum that features a wide range of crystal objects’d art like jewelry, Christmas ornaments, barware, home decor pieces, and stemware.

So, if this is of interest to you, feel free to stop by this attraction on your trip. Once you’re there you can also purchase and take home a small, inexpensive gift.

The Berkshires, MA *in general* (best road trips from Boston)

In the winter, a trip to the Berkshires is another great road trip you can take out of Boston! The trip should take about two hours to complete and you can go cross country skiing and snowshoeing once you’re there.

In fact, according to Karen, numerous hikes are also available through the Berkshire Hills. These hikes include but are not limited to Race Brook Falls, October Mountain Loop and the Bash Bish Falls.

The Bash Bish Falls in particular is where you can go to admire the highest waterfall in the state.

By: Karen of Outdoor Adventure Sampler

Gloucester, MA (best road trips from Boston)

A trip to Gloucester, MA is another great road trip you can take out of Boston. The road trip will take about 50 minutes to complete and you can visit the Good Harbor Beach once you’re there.

In fact, according to Addison Choate, Gloucester has plenty of things to do that are completely under the radar. For example, in Gloucester, you can visit the Hammond Castle Museum that’s located in the Magnolia area on the Atlantic coast.

The castle, which was constructed between 1926 and 1929, was also the home and laboratory of John Hays Hammond, Jr., who was an inventor and pioneer in the study of remote control.

Lexington, MA (best road trips from Boston)

A trip to Lexington, MA is another great road trip you can take out of Boston. The road trip will take about 30 mins to complete and you can visit the Wilson Farm once you’re there.

In fact, according to Trip Savvy, there are a lot of other things you can do in Lexington as well. For example, in Lexington, you can visit the Lexington Battle Green where the American Revolution began. This spot also showcases the Revolutionary Monument which dates all the way back to 1799.

In addition, the Lexington Venue is also a great place to catch a movie. It’s a small town movie theater with two screens that shows a variety of feature and independent films.

Plum Island, MA (best road trips from Boston)

A trip to Plum Island is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit Bob Lobster once you’re there.

In fact, according to New England, there are a lot of other things you can do in Plum Island as well. For example, on the island, you can visit Plum Island Beach which is 42 miles away from Downtown Boston.

Therefore, if you’re planning on checking out this spot for the first time, I highly recommend going before sunset. This will give you the chance to see the beach as the sun sets so that you can take great pictures.

Kennebunkport, ME (best road trips from Boston)

A trip to Kennebunkport, Maine is another great road trip you can take out of Boston. The road trip will take about two hours to complete and you can visit the Seashore Trolley Museum once you’re there.

In fact, according to Vacation Idea, there are a lot of other things you can do in Kennebunkport as well. For example, Kennebunkport has a top rated tourist attraction called the First Families Kennebunkport Museum.

It is operated by The Kennebunkport Historical Society and you can find it in an 1853 Greek Revival home on Main Street in a village.

Lenox, MA (best road trips from Boston)

A trip to Lenox, MA is another great road trip you can take out of Boston! The road trip will take about three hours to complete and you can visit The Mount, Edith Wharton’s Home once you’re there.

In fact, according to New England With Love, there are a lot of other things you can do in Lenox as well. For example, Lenox has a top rated tourist attraction called the Berkshire Scenic Railway Museum.

It is an all-volunteer, non-profit organization dedicated to preserving the history of railroading and trolley lines in the Berkshire Hills of Western Massachusetts.

Ipswich, MA (best road trips from Boston)

A trip to Ipswich, MA, is another great road trip you can take out of Boston. The road trip will take about 40 minutes to complete and you can visit the Castle Hill on the Crane Estate once you’re there.

In fact, according to Travel Lens, there are a lot of other things you can do in Ipswich as well. For example, in Ipswich, you can meet some wolves at a top rated tourist attraction called the Wolf Hollow.

It is a non-profit wolf sanctuary and educational hub that’s dedicated to preserving the wolves in the wild with education and exposure.

Ogunquit, ME (best road trips from Boston)

A trip to Ogunquit, ME is another great road trip you can take out of Boston! The road trip will take about an hour and 20 minutes to complete and you can visit Ogunquit Beach once you’re there.

In fact, according to Visit Maine, there are a lot of other things you can do in Ogunquit as well. For example, in Ogunquit, you can visit a top rated tourist attraction called Perkins Cove.

It is a small turn of the century fishing village that draws in great crowds every summer due to the boutique shops and fresh seafood.

Kittery, ME (best road trips from Boston)

A trip to Kittery, ME is another great road trip you can take out of Boston. The road trip will take about an hour to complete and you can visit the Kittery Historical and Naval Museum once you’re there.

In fact, according to The Crazy Tourist, there are a lot of other things you can do in Kittery as well. For example, in Kittery, you can visit a top rated tourist attraction called Badger’s Island.

Badger’s Island is an island that sits right in the middle of the Piscataqua River where several important boats were built many years ago. These boats include but are not limited to the Ranger, America, and Raleigh.

Westford, MA (best road trips from Boston)

A trip to Westford, MA is another great road trip you can take out of Boston. The road trip will take about 45 minutes to complete and you can visit The Butterfly Place once you’re there.

In fact, according to Boston Central, there are a lot of other things you can do in Westford as well. For example, in Westford, you can visit a top rated tourist attraction called Kimball Farm Mini Golf.

This attraction has two 18 hole adventure style miniature golf courses as well as a 6000 square foot bumper boat pond.

Fall River, MA (best road trips from Boston)

Fall River, MA is another great road trip you can do out of Boston! The road trip will take about an hour to complete and you can visit Battleship Cove once you’re there.

In fact, according to Kathyrn, this small city has many unique stops to offer to your average road tripper. For example, just down Water Street, you’ll find the City Gates Plaza, which is a tribute to the city’s sister city of Ponta Delgata.

In addition, this city also has the home of the famous axe murderer, Lizzie Borden. However, since the home is vacant, it is now being used as a Bed & Breakfast for tourists. So, if you like dark tourism and psychopathy, this spot is for you!

By: Kathryn of Staying Afloat Blog

Middlefield, MA (best road trips from Boston)

A trip to Middlefield, MA, is another great road trip you can take out of Boston! The road trip will take about three hours to complete and you can visit the Glendale Falls once you’re there.

In fact, according to Tripadvisor, there are a lot of other things you can do in Middlefield as well. For example, in Middlefield, you can check out Andrew’s gallery, DeVries Fine Art International Inc., at the River Studio in the city.

The studio also has different series of Andrew’s sculptures that include but are not limited to dance, figurative, and abstract.

Sutton, MA (best road trips from Boston)

A trip to Sutton, MA is another great road trip you can do from Boston! The road trip will take about an hour to complete and you can hike the Purgatory Chasm once you’re there.

In fact, according to Sutton Mass, there are a lot of other things you can do in Sutton as well. For example, in Sutton, you can visit a top rated tourist attraction called Waters Farm.

In Waters Farm, you can enjoy horse drawn carriages in the summer, sleigh rides in the winter, and a wealth of other fun activities in between.

In fact, in my opinion, summer is the best time to visit since you’ll have the opportunity to participate in one of their festivals.

New Bedford, MA (best road trips from Boston)

A trip to New Bedford is another great road trip you can take from Boston! The road trip will take about an hour to complete and you can follow the Self-Guided New Bedford Art Walk once you’re there.

In fact, according to Kathyrn, this small city has many unique stops to offer to your average road tripper. For example, in New Bedford, you can explore a beautiful collection of murals scattered across the city.

In addition, you can also immerse yourself in New Bedford’s beautiful architecture by walking along the city’s cobblestone streets.

By: Kathryn of Staying Afloat Blog

Cape Cod, MA *in general* (best road trips from Boston)

A trip to Cape Cod is another great road trip you can take out of Boston! The road trip will take about an hour to complete and you can stop by the Cape Cod National Seashore once you’re there.

In fact, according to the U.S. News and World Report, there are a lot of other things you can do in Cape Cod as well. For example, in Cape Cod, you can visit a top rated tourist attraction called Cape Cod Rail Trail.

Previously known as the Old Colony Railroad corridor, the Cape Cod Rail Trail is considered to be one of the best biking trails in New England.

Agawam, MA (best road trips from Boston)

A trip to Agawam, MA is another great road trip you can take out of Boston! The road trip will take about two hours to complete and you can visit Six Flags New England once you’re there.

In fact, according to Theme Parks and Entertainment, Six Flags New England is known for having some of the best roller coasters in the world. These roller coasters include but are not limited to The Great Chase, Catwoman’s Whip, and Goliath.

Superman The Ride is also the best ranked roller coaster in the park while The Great Chase is the worst.

Overall, I really hope you enjoyed this post on the 30 best road trips you can take from Boston! Please let me know in the comments down below which road trip destination you would like to visit the most! I would love to hear from you. 🙂

P.S. If you’re looking for some things to do in NYC, check out this post on the 101 things you can do alone while you’re there.

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