15 Best Small Towns to Visit in Massachusetts

One of the original 13 colonies, Massachusetts is now also the most populous state in New England. The Pilgrims actually established the first colony there at Plymouth, and a neighboring town, Salem, held the infamous witch trials.

Rich in history as well as beautiful countryside and beach towns, Massachusetts is an appealing vacation destination for anyone. Leave the sprawling metropolis and relax for a few days.

Check out our list of the best small towns to visit in Massachusetts:

1. Stockbridge, Massachusetts

Stockbridge is a town located in Berkshire County. A resort area perfect for any season, this artsy, picturesque town was first settled by missionaries in 1734. They established a mission for Native Americans who had earned this township as a reward for their support of the British during the French and Indian Wars. The town has long since changed into a resort destination perfect for your next mental break.

A big part of the appeal at Stockbridge is the art colony that traditionally formed a part of the town. Norman Rockwell painted a lot of his artwork here and the town is now home to the Norman Rockwell Museum. Stroll through scenic downtown or spend a few hours at the Berkshire Botanical Gardens before browsing the local art galleries or taking a yoga class at Kripalu Center for Yoga and Health. You’ll probably be able to recognize some of the lovely scenes from Rockwell paintings!

2. Hadley, Massachusetts

Located in Hampshire County, Hadley is small but popular with visitors because of its ideal location along Route 9. A town with a long US history, it was first settled in 1659 by Puritans. Hadley is even connected to some of the witch hunts during those years: Mary Webster, wife to the son of one of Hadley’s founders, was tried and acquitted of witchcraft here in town!

Don’t worry, the town hasn’t had trials for centuries, but stop by to check out the cute downtown area or the shopping at Hampshire Mall. The famous University of Amherst is not far away, either. Stay for a few days at Hadley Meadow Bed and Breakfast, a place perfect to rest your feet after a day of hiking at Silvio O Conte National Fish and Wildlife Refuge. Step back in time at the Porter Phelps Huntington House Museum and disconnect from modern life while in Hadley.

3. Provincetown, Massachusetts

A quaint New England town at the tip of Cape Cod, Provincetown is a coastal resort destination known for its beaches, harbor and artists, all of which draw in the tourism. The Cape Cod area was first discovered by European explorers in 1602, and named thus after they caught a lot of codfish. The Pilgrims first anchored here in the harbor in 1620, where they then wrote and signed the Mayflower Compact. Even though the Pilgrims later settled across the bay, Provincetown continues to draw people here to this day with its historical importance and appealing beaches.

Come to Provincetown and see the Pilgrim Monument, designed by Willard Sears after the Torre del Mangia in Siena. The town itself boasts 8 buildings and two historic attractions on the National Register of Historic Places – make sure to explore Provincetown Historic District and Dune Shacks of Peaked Hill Bars Historic District! An artist’s colony and subsequent vacation destination for alternative lifestyle tourists, Provincetown has long promoted gay tourism. Attend one of the town’s many festivals and enjoy yourself at any of them, like the Portuguese Festival, Bear Week, or PBG’s Carnival Festival. Don’t forget the sunblock before you hit the beach!

4. Rockport, Massachusetts

Rockport is located in Essex County, about 40 miles from Boston. Previously an uninhabited area of Cape Ann, Rockport gradually began forming in the 1800s due to the exportation of granite and the establishment of stone quarries. Even after this demand subsided, an artist’s colony continued to thrive to morph Rockport into a vacation destination.

Tourists still come out to Rockport for its well-known rocky beaches. Walk down to the harbor to see the a red fishing shack, Motif Number 1, that has been the subject of hundreds of paintings and photographs and is still visited by aspiring painters. Be sure to try the lobster when you are here – lobster fishing is a local part of the economy. Visit Halibut Point State Park to see an old granite quartz, Babson Farm, before heading to Bearskin Neck, converted fisherman shacks that are now popular restaurants and galleries. Snap some photos or maybe pick up those paintbrushes again and memorialize your trip!

5. Westford, Massachusetts

Another historic Massachusetts town, Westford is in Middlesex County and has notable ties to the Revolutionary War: Paul Revere’s son attended school here and both a bell and a weather vane cast by him reside in the town. Now a bustling suburban sprawl town, quality of life is high and the population is happy, something you’ll immediately notice during your visit.

Visit Westford for any of their charming annual events: they have a snow sculpture contest in winter, an Apple Blossom Parade and Carnival in May, and a Strawberry Festival in June to name a few. Bring your skis and hit the slopes at Nashoba Valley ski area or have some ice cream at Kimball Farm. You won’t be disappointed here; there is something to please everyone!

6. Newburyport, Massachusetts

A perfect destination for the avid sailor, Newburyport, located in Essex County, is a historic seaport about 35 miles outside of Boston. Set along the Merrimack river, the town was once a shipping, fishing and shipbuilding hub for trade importers. Nowadays, sailing and boats still bring in a lot of income for the city, but more from the boats docked there recreationally.

Visit this historic town to see the first station built for the Coast Guard, the Cushing House Museum and Garden, and the Newburyport Superior courthouse, the oldest continuously active courthouse in Massachusetts. Take a spin at the year-round ice skating rink, and down along the waterfront and boardwalk. Don’t forget the quaint downtown shopping district home to many boutiques. Newburyport is guaranteed to have something appealing for any visitor, even those prone to seasickness.

7. Rowe, Massachusetts

Rowe is a small town (less than 400 people!) in Franklin County, Massachusetts. An area where Native Americans fished and foraged prior to the arrival of the Europeans, it was then used as a fort to guard settlers against raids. Nowadays, Rowe is still surrounded by beautiful nature and is also home to the first nuclear power plant in New England.

Stop in at Rowe and walk to the Village Green and Mill Pond, you’ll see Adams Mountain painting a lovely backdrop to the tranquil scene. If you want to venture outside of town, head to the railroad bridge that crosses the Deerfield River and enjoy the peace that nature offers. Hike around the Upper Bear Swamp Reservoir or Pelham Lake, or visit Monroe State Forest. Rowe is off the beaten path, literally: there are no state highways running through it. It’s the perfect opportunity to leave your worries at home and come out here to take some time away.

8. Oak Bluffs, Massachusetts

Located on Martha’s Vineyard, Oak Bluff awaits your visit. Plan your island getaway here to the town of cute gingerbread cottages and 19th century buildings. Named for the oak groves overlooking Nantucket sound, Oak Bluffs seems planned precisely for your visit!

Take in the views at Ocean Park Gazebo and soak in that ocean breeze. Book yourself a few nights in the historic Oak Bluffs Inn and enjoy a view and delicious food at Nancy’s Restaurant. Have a nap on Inkwell Beach or take a paddle board out onto the waves. Remember that fun is the only priority and Oak Bluffs will make achieving this easy for you.

9. Lenox, Massachusetts

Lenox is a small town in Berkshire County, and is a popular summer destination. Previously an industrial town, it thrived as an art colony in the 1800s – Catharine Sedgwick lived here as well as Nathaniel Hawthorne. Once the railroad found the town in the 1800s, tourists were soon to follow.

Nowadays people come to Lenox for the scenic streets and to visit Tanglewood, summer home to the Boston Symphony Orchestra. Besides being a popular summer destination for the outdoorsmen, Lenox also lovely in the autumn to hike or take your bike out on the paths around Pleasant Valley Sanctuary to see the vibrant colors of the foliage. Don’t forget Lenox in winter, either, because there are many ski resorts in the area. No matter what the season, you can always book yourself some treatments at the Cranwell Spa for some instant relaxation.

10. Concord, Massachusetts

Located in Middlesex County, Concord is part of the Greater Boston area. The town center is right where the confluence of the Sudbury and Assabet rivers forms the Concord River, and is one of the scenes of the Battle of Lexington and Concord, the first conflict of the American Revolutionary War! This historic town also has as prominent literary history, with Ralph Waldo Emerson, Nathaniel Hawthorne and Louisa May Alcott all having been residents here at some point.

Visit Concord to see the battleground location or tour the preserved homes of these famous literary figures, or even if you’re a grape enthusiast – did you know that the Concord grape was developed here? Concord was even the first community to ban the use of single serving plastic bottles. There is so much to appreciate about this bold town which you’ll notice as soon as you walk down Main Street. Visit the Minute Man National Historical Park, the Walden Pond State Reservation, and don’t miss the Sleepy Hollow Cemetery! You can relax at the Concord River and refuel over a meal at 80 Thoreau before continuing your exploration of this Massachusetts gem.

11. Norfolk, Massachusetts

Norfolk, a suburban, rural community in Norfolk County, is nestled in a valley along the Charles River. First established in a push to populate the colonial frontier, the settlement was considered too remote despite offering good agricultural lands and abundant fishing. It was abandoned and then resettled with the establishment of cotton and paper mills.

Stop in for an out of the way, quiet destination. See if you recognize any of the locations from Ted 2 – it was filmed here! Bring your hiking shoes and spend some time at the Stony Brook Wildlife Sanctuary, a beautiful way to enjoy Mother Nature. Enjoy a meal at the Horse N Carriage or relax over a drink at the Eagle Brook Saloon.

12. Maynard, Massachusetts

Maynard, located on the Assabet River in Middlesex County, is named after Amoy Maynard, a businessman who purchased water rights to the Assabet River in the mid-1800s. The mill he constructed made the highest percentage of wool for US military uniforms during the Civil War. While this mill ultimately went bankrupt, it has been preserved by the town and is now a commercial center. There is a clock tower that is home to the oldest, still working, hand-wound clock tower in the US – it takes 1-2 hours to hand-wind it!

Visit Maynard and prepare to be charmed with their shops – they even have a store called “Charmed”. Attend a show at the Fine Arts Theatre Place, and relax. If you’re interested in getting out on the river for fishing, stock up on supplies at Maynard Outdoor Store.

13. Manchester-by-the-Sea, Massachusetts

An enchanting town on Cape Ann, Manchester-by-the-Sea lives up to its name with its scenic beaches and viewpoints. Founded in 1939 by Europeans, it was primarily a fishing community for 200 years. It became a summer holiday destination once a famous poet, Richard Dana, moved there in the mid-1800s. The ritzy Boston crowd then flocked out here to relax in the cool ocean breeze.

Visit Manchester-by-the Sea and spend the day at Singing Beach – the sand “sings” as you walk across it! Climb or admire the famous Eagle Head rock, perfect for rock climbing or pictures. Don’t forget to check out the downtown area, especially the Town Hall. Enjoy a little slice of heaven along the coast next summer.

14. Groton, Massachusetts

Groton is located in Middlesex County. Originally a trading post, Groton is the scene of a battlefield in King Phillip’s War, one of several conflicts between the Native Americans and European settlers. During the war, almost all buildings here were burned by the Native Americans.

The town has rebuilt nicely since those early days, and now you can find plenty of ways to entertain yourself. Have a lovely meal at the Herb Lyceum at Gilson’s, or a cup of coffee at Blackbird Cafe. Take a walk along the Gibbet Hill Barn and Trails or canoe doesn’t the river at Nashoba Paddler. If you make it to Groton in the autumn, check out the hidden gem Autumn Hills Orchard.

15. Deerfield, Massachusetts

Located in Franklin County, Deerfield was the farthest northwestern outpost for the New England settlements until the mid-18th century. Located in the Connecticut River Valley, it witnessed several skirmishes between Native Americans and European settlers in the early colonization of the US.

Nowadays, Deerfield has preserved its past in Historic Deerfield. Wander through and stop in at Old Deerfield Country Store, or the Memorial Hall Museum. Walk out to Pocomtuck Ridge and hike up to appreciate the views. You can always burn calories to save room for Richardson’s Candy Kitchen once you return to town!