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Home Road Trip The best summer road trips in Massachusetts, according to readers

The best summer road trips in Massachusetts, according to readers

by Staff


Readers Say

Readers recommended 23 destinations to visit across the state.

Aerial of Chatham Harbor, the town, and South Beach off of Monomoy Island. Wendy Maeda/Globe Staff

Trying to plan your summer vacation but can’t decide where to go? Massachusetts has some summer vacation spots that are not only beautiful but make for a worthwhile road trip.

We asked readers for their ideal summer road trip destinations in Massachusetts, and you delivered. We received recommendations to 23 of your favorite spots across the state, and the routes to get there. 

We tried our best to bucket the destinations into four regions: west of Boston, north of Boston, south of Boston, and the city of Boston. Of the recommended road trip locations, 67 readers chose Cape Cod towns, 19 readers chose Martha’s Vineyard, and 15 chose Boston. Readers loved these places because of their history, beaches, restaurants, and beauty.

Below you’ll find a guide to the 23 Massachusetts summer road trip destinations, and why readers selected them. We’ve also included a map featuring all the destinations and the most popular route, according to readers. Check out our guide and map out your summer plans. 

Boston 📍

People gather at cafe tables placed in the closed parking lane on Hanover Street in the North End neighborhood of Boston. – AP Photo/Michael Dwyer

Boston is, of course, a must-visit on any summer road trip in Massachusetts. Whether you are living in or near Boston and going to some of your favorite places or visiting for the first time, the city has endless options no matter your age or interest. Boston has history, literature, art, food, and more. We have the Boston Tea Party Ships and Museum to take you back to the Revolutionary War. Or venture on the iconic Freedom Trail, which ranks as a top 10 free attraction in the U.S., according to USA Today readers. The newest attraction to check out will be View Boston, where visitors will have unparalleled views of the city from atop the Prudential Center. Boston also offers a diverse food culture across its many neighborhoods – you’ll find the best pizza in the North End, Irish pubs downtown, and dumplings in Chinatown and beyond.

Boston has more than just restaurants, though. Sports fans are in luck as Fenway Park and TD Garden are great places to see the Red Sox, Bruins, and Celtics. (We are the best sports fans, after all.) If you want to explore Boston’s cultural side, pay a visit to the Institute of Contemporary Art, Isabella Stewart Gardner Museum, or the Museum of Fine Arts where you can see works from Asia, Europe, America, and many more.

North 📍

A visitor walks along Bradley Wharf in Rockport. – Lane Turner/Globe Staff

Beverly

A coastal town with beaches, shopping, and restaurants, any visitor should have no problem filling their day with activities in Beverly. Longing for a relaxing day at the beach? There are plenty of options. Beverly’s Dane Street Beach is large and has play structures for kids, while Pleasantview Park lies adjacent to a small beach. Beverly also has plenty of parks and open spaces to see including Lynch Park which has benches, a performance shell, splash pad, and a rose garden. Aside from its natural seaside beauty, peek into the town’s history at Beverly’s Hospital Point Light Station, or the John Balch House which gives visitors a view into early colonial life. Looking for live entertainment? Dive into a show at The Cabot, where you can see movies or live acts like Elvis Costello who swung by this spring, or head to the North Shore Music Theatre. If you go from July 11 through July 23 you may be able to catch “The Sound of Music.”

Cambridge

Boston may get a lot of attention from visitors, but just across the Charles River, Cambridge is worth the stop according to several readers. Cambridge’s Harvard Square offers enough to fill your whole day. There are plenty of places to eat and drink in Harvard Square, shop at one of their numerous bookstores, or explore the Yard and its iconic John Harvard Statue.

The beautiful architecture on the Harvard grounds isn’t the only highlight that the school has to offer. The Harvard Natural History Museum is a combination of three research museums including the Harvard University Herbaria, the Mineralogical & Geological Museum, and the Museum of Comparative Zoology.

If you’re close to the Boston-Cambridge border, check out the Museum of Science, a perfect place for adults and children that offers exhibits from outer space to dinosaurs.

Gloucester

The city of Gloucester is located on Cape Ann and has the charm of a quaint coastal town but the business of urban life. Residing on the coast, Gloucester has many beaches and parks but also has restaurants, harbor views, and ocean activities. Gloucester has ample beaches to offer for your day in the sun. Go for a lobster roll at Mile Marker One, then head to Good Harbor Beach or Long Beach, both offering white sands and an ocean breeze.

Want an experience a little more adventurous than a trip to the beach? Join Schooner Adventure for sailing trips in the waters off Cape Ann. Schooner Adventure invites you to sail with them all while participating in the fun. However, if you are looking for great views on land, try the Eastern Point Lighthouse, Anniquam Harbor Light Station, or the Ten Pound Island Light. These lighthouses set against the backdrop of the ocean are sure to give you a great picture of your time in Gloucester.

Newburyport

If you need a coastal town with history and charm, stop by scenic Newburyport. The city lies on the shores of the Merrimack River and the Atlantic Ocean and is beloved for its old-timey feel. The cobblestone streets and sidewalk-hugging shops offer guests the chance to meander and explore free of stress. And while the town may have been established in 1635, the shops and restaurants there are anything but old. 

Popular shops in Newburyport include Bobbles & Lace, Soak & Shoreline, and Life is Good. If you are looking for a larger event to do in Newburyport this summer swing by for their Yankee Homecoming celebration, set to take place from July 29 to August 6. The 74th annual celebration will include events like a high school battle of the bands, a Brewfest fundraiser, waterfront concerts, a market, a parade, and fireworks. 

Rockport

Rockport is about an hour north of Boston and worth the visit for the iconic red fishing shack, which is the most painted building in the world, according to Yankee magazine. It is tranquil and breathtaking with its shoreside town and rocky glades, which may be why the town boasts a thriving artist community. Who wouldn’t be inspired in such a place?

The fishing shack, covered in a coat of red paint and wearing a wall full of buoys is known as Motif No. 1. The building alone is a great reason to visit Rockport, especially for any enthusiast of art or history, but you’ll also want to shop along the stretch of Bearskin Neck. If you still long for the beach, Rockport has those too. And be sure to take in the area’s natural beauty at the Halibut Point Reservation

Salem

You may know this town for its Halloween festivities and spooky sites, but Salem has just as much to do in the summer as it does in the fall. Though, you can probably still pack your witch hat — the Salem Witch Museum is still open over the summer if you are interested in learning more about the history of the city and the witch trials.

If you are more interested in the shoreline, pay a visit to Bakers Island Light. The 10-acre light station is located on Bakers Island and has been in operation since 1798. On the island, you can book tours, camp overnight, and explore. Not your cup of tea? Go to Salem Maritime, one of Salem’s national historic sites. There you can visit sites like the Derby House, St. Joseph Hall, and the Colonial Revival Garden. But before you go, stop by E.W. Hobbs for their popcorn, suggested by one Boston.com reader.

Salisbury

Salisbury is a small beach town about 45 miles from Boston. The town has farms, beaches, marshlands, and has approximately 9,200 acres of various types of open space.

With so much land dedicated to open space, you must take in Salisbury’s natural attractions. Salisbury Beach is the perfect combination of both, and a favorite beach among readers. This reservation offers visitors swimming, boating, fishing, play spaces, and scenic areas.

South 📍

People fill the sidewalk on Main Street in Chatham.  – John Tlumacki/Globe Staff Photo

Chatham

If you are going to Cape Cod, several readers recommend visiting Chatham. Making up the elbow of the Cape Cod arm, Chatham is surrounded by water on three sides. It has 66 miles of coastline and over 1,000 acres of conservation land. Chatham is picturesque with its miles of coastline and breathtaking beaches.

For those who are hoping to make this a stop on their Massachusetts road trip, there are a few places you should definitely check out. For the beachgoers, Harding’s Beach and Chatham Lighthouse Beach which features the Chatham Lighthouse are a must. If your family is more interested in learning about the town or experiencing its history then perhaps the Chatham Fish Pier or Godfrey Windmill which was built in 1797. No matter what your family chooses to visit on your road trip Chatham has a lot of great options.

Dennis

Another Cape Cod town, Dennis is located along Nantucket Sound and Cape Cod Bay. Of course, the town is known for its beautiful beaches, and it sure has a few. Dennis can claim 20 beaches located along Cape Cod Bay and Nantucket Sound. Dennis is made up of five villages including Dennis, Dennis Port, East Dennis, South Dennis, and West Dennis. Each of the five villages makes up the quaint town that has made our road trip list.

Now, you could go to the beach again, but if you hit any of our previous road trip stops you may be all beached out. Instead, try the Cape Playhouse which is said to have the longest-running professional summer theater in America. Before the show, stop by The Lighthouse Inn for a beachfront meal. 

Eastham

Eastham is located on Cape Cod, with much of it falling within the National Seashore which is made up of almost 40 miles of beaches, ponds, marshes, and historic sites. Eastham is also home to the Nauset Light which is an iconic landmark known for lighting the way for ships since the 19th century. 

So of course, Nauset Light is the first suggestion we have on our list. After you visit the light take a stroll down Nauset Beach and wait for the sunset, it’s said to have beautiful views. The town has many hiking trails that should be on your list when you visit, too. Check out the Red Maple Swamp Trail and the Fort Hill Trail.

Falmouth

Falmouth is on the southwestern coast of Cape Cod, and the shoreside town is the perfect attraction any day this summer be it beaches or biking. A Boston.com reader suggested Old Silver Beach which is perfect for beachcombing or other seaside activities. Another great seaside activity is venturing out along the Shining Sea Bikeway, which is a 10.7-mile bike path through Falmouth’s woodlands, marshes, and coast.

If you happen to make your trip there in August, you may get to experience the Falmouth Road Race which is held annually. Looking to liven up your road trip experience with a bit of music? Check out Falmouth Jazz which has hosted live jazz for over 50 years.

Harwich

Harwich is located on the southeastern coast of Cape Cod and is made up of seven villages including East Harwich, Harwich Center, Harwich Port, North Harwich, Pleasant Lake, South Harwich, and West Harwich. Beach Village has something special for guests to explore.  Harwich Port, which was specifically suggested by a Boston.com reader, has a busy Main Street area filled with art galleries, restaurants, and small shops. Harwich Port is also home to Allen Harbor and Saquatucket Harbor which have beautiful waterfront views and boating activities. 

If you’re headed to Harwich, your first stop should be the Cape Cod Lavender Farm which is surrounded by over 75 acres of conservation land and has over 7,000 plants. If you’re looking for a new summer read, visit  Below the Brine Bookshop which describes itself as “a tiny, vibrant, independent bookstore.”

Hyannis

Hyannis is located on the southern coast of Cape Cod and has a busy downtown area full of shops, restaurants, activities, and entertainment. Hyannis also has a unique ferry service that allows visitors to spend part of their day on the islands of Martha’s Vineyard and Nantucket. 

Martha’s Vineyard (Edgartown)

Martha’s Vineyard is an island south of Cape Cod known for its small towns, beaches, and natural beauty. Six towns make up the Vineyard, which are Aquinnah, Chilmark, Edgartown, Oak Bluffs, Tisbury, and West Tisbury. Edgartown was noted as a must-see by Boston.com reader, Brett.

If you travel to Edgartown first on your Martha’s Vineyard day trip, go see the Old Whaling Church. The church is a historic landmark in Edgartown and also hosts concerts. Next, explore the Aquinnah Cliffs, which overlooks the ocean and is home to the historic Aquinnah Lighthouse. Then check out the “Gingerbread Cottages.” While they are not the ones you can eat, these 318 brightly colored houses are still a sight to see.

Nantucket

About 14 miles of charming towns, beaches, conservation land, and maritime history, Nantucket is another island off of Massachusetts worth visiting, according to readers It is about 30 miles of Cape Cod and dates back to 1659 when it was settled and became one of the major whaling ports in America.

Because Nantucket’s history is founded on the whaling industry you might want to check out  the island’s Whaling Museum. With approximately 80 miles of coastline to explore, visiting a beach is a must, as is experiencing the island’s hiking trails. About 46% of Nantucket is protected land, giving visitors a unique and “visually dramatic” look at Nantucket’s flora and fauna. Some hiking spots to check out on your trip are Stanford Farm, Squam Farm, and the Middle Moors

Plymouth

Known as “America’s hometown,” Plymouth is rich with history and a scenic harborside. Many may know this town by its Plymouth Rock. You can visit the rock that signifies the site where pilgrims first arrived, and you can also see the Mayflower II museum to learn more about the town’s history.

The downtown area offers plenty of options ranging from American food, seafood, Italian, Greek, and more. Readers have previously recommended stopping at places like the Cabby Shack Restaurant & Pub and Ziggy’s Ice Cream. Don’t miss the Plymouth Center for the Arts to see the art galleries or even take a class.

Provincetown

At the tip of Cape Cod lies Provincetown, where you can meet just about all of your road trip needs. Provincetown has pristine beaches, art, shops, entertainment, water activities, and is known for its LGBTQ+ community.

The options are endless, but if you have to pick maybe take a walk down Commercial Street. There’s so much to see from shops to restaurants to colorful homes, you won’t leave disappointed. When your day is winding down, take a walk down MacMillan Pier to catch the last rays of sun by the water.

“Provincetown is the only place I truly feel I can be myself without judgement,” Boston.com reader AJ wrote. 

Truro

Truro is located closer to the end of the Cape Cod curve but is only about two hours outside of Boston. Truro has two villages which are Truro and South Truro, making it one of the more calm and quiet locations in the Cape. 

In Truro, you can relax on the beaches, explore the area on the Pilgrim Spring Trail, or visit the Truro Vineyards of Cape Cod. After those activities, you may want to make your way over to the  Highland Light, which is the oldest lighthouse on Cape Cod. Between vineyards, beaches, and the Highland Light, Truro has plenty to offer you on your summer road trip.

“Truro offers the best cape cod beaches, national preserve, bike trails, camping, rentals, [and] cabins,” Kathleen M. in Quincy said. “It’s a true Cape seashore vacation.” 

Yarmouth 

Yarmouth is about 75 miles from Boston on the southern coast of Cape Cod. It’s made up of three villages which are South Yarmouth, West Yarmouth, and Yarmouth Port. South Yarmouth was recommended by multiple Boston.com readers, including another vote from Kathleen M. who recommended the town it for its beaches and relaxing environment. 

Make sure to add the Sand Sculpture Trail to your list. The trail will feature 32 unique sand sculptures and is a perfect photo opportunity. You can also check out the Tugboats for dinner which will treat you to excellent food and a view of the Hyannis Harbor.

West 📍

Tanglewood. – Photo © Stu Rosner 2011

Concord

Just northwest of Boston, Concord is full of historic beauty. From the pond where Henry David Thoreau lived nearby to Orchard House where Louisa May Alcott wrote “Little Women” to Ralph Waldo Emerson’s “Self-Reliance” origins, Concord is the perfect road trip stop for those who love history and literature. Concord is also where the infamous Battle of Lexington and Concord occurred and the American War of Independence started. Concord also has a beautiful landscape with many green spaces to explore including the Wright Woods and the Minute Man National Historic Park where visitors get the chance to explore the battlefields of the Revolution. Be sure to stop in downtown Concord where you can do some shopping at places like Nesting, a reader favorite

Lenox

You may know Lenox by its music venue Tanglewood, which frequently hosts the Boston Symphony Orchestra among other performers. Lenox lies in the western region of Massachusetts, a perfect place to get away from bustling city life and enjoy nature. Tony G, in the South Shore, recommended Lenox and the Berkshires “for quiet, relaxing non-beach activities.” To get away from the noise, check out places like Kennedy Park and Lenox Mountain. Lenox has the Mass Audubon Pleasant Valley Wildlife Sanctuary for visitors that are enthusiastic about the outdoors. The Sanctuary has trails throughout its 1,000 acres of forest, wetlands, and meadows lining the Lenox Mountain. Aside from Tanglewood, Lenox also has plenty of performing arts groups putting on shows in the summer like Shakespeare & Company which holds shows from reviving the classics to hosting the LuluFest Lenox Jazz Festival.

Done with a long day exploring? Visit ​​On a Roll Cafe and Catering Co. where you can take your luncheon to the “heart of the Berkshires.”

Walpole

Looking for something niche to do on your road trip? Walpole may be the perfect place to find what you’re looking for. The town is about 27 miles south west of Boston and offers a quiet refuge from the city. Walpole has restaurants to enjoy if you are just passing through like Farmer in the Dell and Clyde’s Road House. For some of our readers, they’d even recommend stopping by Papa Gino’s, a favorite spot for pizza. Boston.com reader, Devin, said that their go-to recommendation would be Francis William Bird Park. What could be considered the town’s hidden gem, the park boasts 89 acres of fields, tree groves, ponds, and brooks. The park was built to offer visitors a mix of relaxation and recreation and may be the perfect spot to picnic and play outdoors with the family on your summer road trip.

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