10 Most Overlooked Massachusetts Towns For 2025

You might have strolled down the cobblestone streets in Boston, vacationed on the sandy shores of Cape Cod, and even witnessed the kaleidoscopic fall foliage in the Berkshires. But if you think you’ve seen all Massachusetts has to offer, you'll be surprised by just how many more gems are waiting to be discovered. Beyond the well-trodden destinations and outside the major highways, the Bay State harbors a selection of under-the-radar towns oozing history, charm, and character.

These overlooked gems deserve a spot on your upcoming itinerary, whether you're chasing small-town charm, hidden local flavors, or unexpected natural splendor. From the beachside beauty of Yarmouth to the riverside allure of Amesbury, here are overlooked Massachusetts towns for 2025.

Yarmouth

This hidden gem on Cape Cod enchants travelers with its pristine coastal scenery, historic sites, and popular festivals. Yarmouth is a go-to summer destination, thanks to its abundance of sand-swept beaches. The popular Seagull Beach offers an extensive stretch of sand for sunbathers, picnickers, and beachcombers, with sweeping views of the Nantucket Sound stretching into the horizon. You can take a trip down memory lane at Captain Bangs Hallet House for a glimpse of Victorian life inside a well-furnished sea captain's home.

Alternatively, opt for an immersive cultural experience at the Cultural Center of Cape Cod, where galleries, music, performances, and culinary experiences showcase different facets of Yarmouth's heritage. Finally, don't miss out on the annual Yarmouth Seaside Festival, which brings together crafters, foodies, musicians, and everybody else for a fun time on the sand.

Amesbury

Amesbury is a quintessential New England borough on the banks of the Merrimack River with a lovely combination of fascinating history and adorable natural scenery. With a history dating back over 350 years, the town tells a fascinating story through its different historical markers. This includes the Macy-Colby House, which was built in the mid-1600s and serves as a rare example of saltbox architecture. Also, the Industrial History Center pays tribute to the community's enduring industrial heritage to educate the public through tours, programs, and exhibitions.

Outdoor lovers can take it easy on the grassy lawns of Batchelder Park and revel in the relaxed atmosphere. The park is perched at the top of Po Hill, which places guests at a pedestal to enjoy scenic views east of the town, and even the Atlantic Ocean on a clear day.

Williamstown

This quaint college town lies in the Massachusetts Berkshires and impressively blends nature, community, and culture to grant visitors an unforgettable stay. Home to Williams College, art and culture are at the heart of the community, with fans coming from across the region to watch an entertaining lineup of live performances at the Williamstown Theatre Festival. This is backed by world-class exhibitions at the Williams College Museum of Art, which displays sophisticated pieces of American modernist art.

The wonderful outdoors beckon at Mountain Meadow Preserve, where residents have access to 180 acres of forest, open fields, and wildlife meadow against the scenic backdrop of the Green and the Berkshire Mountains. Finally, tourists are welcome to mingle and learn from the friendly residents during the Williamstown Farmers Market as they sample their different farm produce.

Swampscott

Despite the overbearing shadow of nearby Boston, Swampscott still manages to impress first-timers with its scenic beaches, historical gems, and retail therapy opportunities. People love to gather at Beach Bluff Park and enjoy the glistening ocean waters and the setting sun. The park hosts a miniature Stonehenge that adds to its allure among vacationers. A series of retail stores and dining venues at Vinnin Square Plaza caters to the needs and desires of casual shoppers and culinary enthusiasts.

Meanwhile, those who appreciate nostalgic encounters can visit the Mary Baker Eddy Historic Site. Constructed in the 1800s, the historic dwelling housed Mary Baker Eddy, an author and religious leader of Christian Science.

Ipswich

35 minutes from Salem, Ipswich is an underrated gem in Essex County and is regarded by many as one of the best-preserved Puritan towns in America. According to the Ipswich Museum, the community's rich heritage stretches almost four centuries, and this is presented through more than 200,000 interactive exhibits. The Castle Hill on the Crane Estate is a sight to behold with its combination of physical grandiosity and architectural splendor. Set on a 2,100-acre property, the English-style mansion boasts 59 rooms and a luxuriously landscaped yard with dazzling greenery.

Outdoorsy guests are spoiled for choice, given the 40 miles of horseback riding and hiking trails awaiting exploration at Willowdale State Forest. Furthermore, you can head to the shores and leisurely comb the smooth sands at Sandy Point State Reservation, while taking in the ocean views.

Groton

Groton's location in the Greater Boston metropolitan area keeps it from receiving as many tourists as it deserves. This charming village has a little bit of everything, whether you are a fan of nature, history, or music. The Rocky Hill Wildlife Sanctuary perfectly exemplifies the town's outdoor appeal. Spread over 420 acres, this diverse ecosystem supports an array of plant and animal life, and you can spot beavers, porcupines, moose, and herons in their natural habitat.

The remains of Bancroft's Castle offer a feel of Groton's yesteryears. Built at the start of the 20th century, the building burned down in 1932 after a fireworks accident, leaving only the outer walls intact. Groton also treats theater lovers to electrifying musical performances at the Groton Hill Music Center, home to two stages where recitals, lectures, concerts, and lessons are held.

Sandwich

Hidden history collides with undiscovered coastal beauty to make Sandwich one of the most overlooked Massachusetts towns for 2025. Sandwich's rich heritage is intertwined with the glass-making industry, a history well-preserved at the Sandwich Glass Museum. A collection of vintage glassware produced by the Boston & Sandwich Glass Factory offers a glimpse into its Victorian heyday. Meanwhile, the Hoxie House transports guests further back into the 17th century inside one of the oldest houses in New England.

A leisurely stroll along the Sandwich Boardwalk places you on the perfect platform to admire the town's undisturbed beauty, as you transition from a marsh area to a spectacular beach along a 1,300-foot promenade. Lastly, don't leave without sampling the town's fantastic flavors at Fishermen's View Seafood Market and Restaurant.

Edgartown

This remote island getaway on Martha's Vineyard impresses visitors with its sandy beaches, picturesque lighthouses, and undisturbed nature. Edgartown is a beach lover's paradise and rewards vacationers with an array of options, including Katama Beach. It is popular among swimmers, surfers, and birdwatchers. The imposing Edgartown Harbor Lighthouse dominates the island's skyline and reminds first-timers of the town's rich maritime heritage. It was completed in 1828 and remains a recognizable symbol of the community.

Further inland, nature enthusiasts can find the perfect escape at the Mytoi Japanese Garden. This small oasis straddles about 14 acres yet boasts a rich ecosystem of exotic plants, seasonal flowers, a pond, and serene walking trails, ideal for meditation. Before leaving, consider downing a pint or two of local brews at Bad Martha Farmers Brewery.

Stockbridge

This picturesque New England village lies in the foothills of the Berkshire Mountains in western Massachusetts, surrounded by raw natural beauty and home to magnificent Victorian mansions. Stockbridge's serene outdoor scenery is at its best at the Berkshire Botanical Garden. Covering about 24 acres, this dazzling oasis displays a colorful collection of 3,000 native plant species. Calm walkways crisscross the space, allowing nature lovers to stroll through and revel in the tranquil air.

The town's rich history shows in the rustic building style of the Naumkeag museum. Constructed in the 1800s, this Gilded Age mansion boasts about 40 rooms with period furnishings and antiques that tell a fascinating story about the past. For art lovers, a trip to the Norman Rockwell Museum introduces them to his most significant art collection, comprising a mix of paintings, drawings, and other memorabilia.

New Marlborough

New Marlborough is another quintessential gem in Berkshire County, where nature and history collide to offer vacationers a fantastic escape. It has boundless options for the outdoors inclined, starting with a short and comfortable hike to Umpachene Falls. This gorgeous cascade plunges 40 feet into the Konkapot River, creating a storybook scene that calls for a photo session. Meanwhile, over 400 acres of open fields, forests, meadows, and hayfields at Questing invite guests to hike and picnic around this colonial site.

New Marlborough also welcomes wine aficionados for a wine tasting experience at Les Trois Emme Winery. The dog-friendly establishment offers relaxed picnic grounds where you can bring a glass and enjoy fine wines while reveling in small-town charm.

Hidden Gems in Massachusetts Beckon

While Boston has long grabbed headlines revolving around tourism in Massachusetts, this is an excellent time to seek a novel experience outside the vibrant hub and explore off-the-beaten-path. Luckily, these overlooked Massachusetts towns for 2025 don't disappoint with their diverse cultures, fascinating histories, and unique outdoor adventures in the United States. Whether you want to savor island vibes in Edgartown or bask in the tranquil mountainside atmosphere of Stockbridge, these enticing Bay State destinations deliver a gratifying getaway from the city.