12 Overlooked Towns In Massachusetts Worth Visiting
Most people traveling to Massachusetts are familiar with Boston, Cape Cod, and the Berkshires. While these are some of the most exquisite destinations in the state, drawing millions of visitors annually from all over the United States, there are numerous other gems worth discovering that unfairly remain under the radar. Venturing outside the major tourist hubs and onto the deserted country roads culminates in an unforgettable experience steeped in Revolutionary War-era echoes, timeless New England heritage, farm-fresh cuisine, and peaceful outdoor escapes.
From strolling along the rugged coastline of Rockport to wandering the forested trails of North Adams in the Berkshires, these hidden towns promise a soulful and surprising journey. Whether a New England native or visiting from a distant state, here are the most underrated towns in Massachusetts worth visiting.
Hingham
Hingham's proximity to Boston causes it to be overlooked by tourists visiting the Massachusetts coastal region. However, it has an interesting colonial backstory worth exploring at the Hingham Historical Society. The facility preserves the area's history through several vintage properties, historical narrations, archives, and artifacts. Outdoor enthusiasts have no shortage of options when venturing into the open spaces, but Wompatuck State Park is among the best. Spanning over 3,500 acres, this year-round recreational hub features a massive campground, endless miles of trails, and scenic driving routes.
Alternatively, you can go to Bathing Beach for more relaxed activities on a sandy swimming beach overlooking a beautiful marina. Finally, be sure to meet local bakers, farmers, crafters, and artisans at the Hingham Farmers Market for a taste of authentic New England flavors.
Orleans
This quaint community on Cape Cod charms with a mix of rich history, pristine beaches, and vibrant arts. Orleans traces its origins to the 18th century and preserves its fascinating backstory at the Orleans Historical Society. Here, guests can peruse a collection of photographs, records, archives, and other artifacts to experience the community's evolutionary journey over the years. Additionally, art plays a significant role in local culture, with a keen appreciation for both visual and performance art. Interested visitors can watch entertaining presentations at the Academy of Performing Arts, including dance shows and music demos.
Lastly, beaches are some of the major draws for vacationers in Orleans. Many of them love to converge at Skaket Beach for swimming, sunbathing, and lounging while delighting in soothing panoramas of Cape Cod.
Ipswich
Ipswich is a tranquil beachside town in Essex County, renowned for its stunning natural surroundings. It is home to beaches, forests, and farms, making it an ideal destination for outdoor enthusiasts. At Crane Beach, visitors can enjoy a spectacular stretch of sand with smooth trails and crystal-clear waters, making it an ideal spot for a refreshing dip. Meanwhile, 40 miles of trails wind through Willowdale State Forest, taking you away from the shores and into a lush wilderness area with hiking, wildlife watching, and picnicking opportunities.
The town's rich past comes alive at the Ipswich Museum, where an extensive selection of paintings, drawings, photographs, and other memorabilia documents centuries of local history. While in the town, don't miss the chance to sample finely aged wines at 1634 Meadery.
Edgartown
Edgartown is a small summer escape on Martha's Vineyard, renowned by locals for its stunning lighthouses, beautiful beaches, and undisturbed natural habitats. First-timers in the town automatically notice the imposing Edgartown Harbor Lighthouse. It is one of five lighthouses in the area, alluding to its rich nautical heritage. And while no beach is a wrong answer here, Katama Beach has a particular gravity. This adorable space is perfect for surfers, swimmers, sunbathers, and birdwatchers, boasting terrific vistas of Katama Bay.
Away from the water, those looking for a different style of meditation can find time at Mytoi Japanese Garden to calmly wander and take in the curated beauty. This 14-acre oasis boasts a thriving ecosystem, featuring relaxed trails and a pristine pond perfect for peaceful reflection. Lastly, try out the local beer scene with a pint at Bad Martha Farmers Brewery.
North Adams
North Adams transformed from an industrial mill city to a vibrant cultural hub in the Berkshires with world-class art centers. The town is famously home to the Massachusetts Museum of Contemporary Art. This restored 1800s factory campus has become one of the most vibrant venues in the state, catering to both visual and performing arts. Apart from experiencing the arts, tourists can enjoy some retail therapy at the Norad Mill Shopping Center.
Like any other destination in the Berkshires, North Adams offers plenty of outdoor opportunities. Adventure freaks can head to Natural Bridge State Park for peaceful woodland walks. The area stuns newcomers with its 60-foot gorge and man-made dam, which provide great photo ops.
Wellfleet
Wellfleet is a charming town on the Massachusetts coast, situated between the "tip" and "elbow" of Cape Cod and known for its relaxing vibe and excellent oysters. Unrestricted access to the beach makes it a great weekend escape, with the opportunity to hike dunes, swim, surf, and sunbathe on the sandy shoreline of White Crest Beach. The Great Island Trail offers easygoing hiking excursions along a 5-mile loop that passes through swamp, beach, and forest habitats. The peaceful and isolated atmosphere is ideal for meditating, spoiling guests with breathtaking views of the Cape Cod National Seashore.
The town offers visitors a taste of its arts and culture scene at the Wellfleet Harbor Actors Theater, which captivates with film screenings, contemporary plays, and kids' shows, as well as other stage presentations in front of an enthusiastic audience.
Great Barrington
This enchanting borough in the Berkshires delights newcomers with its walkable downtown and vibrant Main Street, set against the lush mountains of southwestern Massachusetts. Tourists in Great Barrington enjoy a delightful balance between indoor and outdoor attractions, with access to rugged climbing trails at Monument Mountain Reservation that allow you to experience the region's stunning countryside scenery. In winter, roads lead to Ski Butternut, a resort at the top of the eponymous mountain, for snowboarding and skiing fun on a 10-acre playground.
Meanwhile, downtown Great Barrington connects visitors with the arts at the Mahiawe Performing Arts Center, which showcases all forms of theatrical presentations in a gorgeous 1905 grand theater. Additionally, there's time to indulge in the sumptuous local dishes and drinks at Barrington Brewery & Restaurant, which features a menu that incorporates American pub grub and handcrafted beers.
Northampton
This lovely town in Hampshire County stands out for its quirky, bohemian vibe, providing a conducive environment for artists, musicians, writers, and academics to thrive. Vacationers enjoy an immersive cultural experience in Northampton, with the opportunity to browse a world-class collection of vintage and contemporary pieces across four floors of galleries at the Smith College Museum of Art. Besides the visual arts, the Academy of Music presents unmissable performance art shows in an intimate theater setting, where enthusiasts come to watch dance, plays, musicals, and more.
Northampton hosts the state-famous Botanic Garden of Smith College, home to, among other wonders, the largest ginkgo tree in the state, whose leaf-dropping in late fall is a must-see event. The garden also features an amazing display of tropical and subtropical plants with quiet walking paths winding through them.
Rockport
This harbor village in Essex County is one of the most underrated towns in Massachusetts worth visiting, boasting a winning combination of rugged shoreline, stunning ocean views, and whimsical historical markers. A trip to Bearskin Neck allows newcomers to appreciate Rockport's pristine harbor scene, featuring terrific panoramas of the Atlantic Ocean on a vibrant corridor. Meanwhile, those who relax by the water can head to Front Beach, a sandy stretch near the town center where people go to sunbathe, stroll, and swim.
The Rockport Arts Association & Museum supports the local arts community by exhibiting a curated collection of pieces by local artists, which you can browse and purchase. Lastly, don't miss the opportunity to savor scrumptious seafood cuisine at Brackett's Oceanview Restaurant.
Sandwich
Sandwich is the ultimate beachside getaway on Cape Cod, rooted in history and boasting a proud legacy as the oldest town in the region. You can learn about its captivating history at the Sandwich Glass Museum, which displays a wonderful collection of Victorian-era glass to interpret Sandwich's rich glassmaking heritage and preserve memories of the once thriving Boston and Sandwich Glass Factory. Additionally, the Hoxie House is a rare portal to history, still standing despite being built in the 17th century, one of the oldest structures in New England. Tours guide visitors through its simple, enlightening interiors.
Sandwich welcomes sightseers to soak in its pristine natural beauty during a laid-back stroll on the Sandwich Boardwalk, which spans over a deserted beach and marsh, offering wide-open views of the water as far as the eye can see.
Concord
Rich American Revolutionary War history comes alive in this old borough northwest of Boston, home to numerous landmarks and monuments that share the story of iconic battles. Concord is home to the famous North Bridge, believed to be the site where the first shots that triggered the Revolutionary War were fired in 1775. A short walk from the bridge, you will come across the Old Manse, which dates back to 1770 and preserves various period heirlooms of the Emerson family, painting a portrait of life in the pre-Revolutionary War era.
Apart from the enthralling history lesson, Concord offers an escape for ardent outdoorsmen at Great Meadows National Wildlife Refuge, where recreational opportunities such as birdwatching, hiking, and camping await across diverse habitats. Those looking for a more sedentary day outdoors can always head to beautiful Walden Beach, a perennial favorite among locals and visitors alike.
Williamstown
Undisturbed nature, vibrant arts, and a sense of community in this beautiful college town in Berkshire County. Williamstown is an excellent destination for culture vultures, housing world-class art centers like the Williams College Museum of Art. This showcases an impressive library of sophisticated art by talented American creators. Furthermore, it stages a lineup of compelling live productions at the Williamstown Theatre Festival, featuring classic and modern plays in a premier venue.
Williamstown's general sense of warmth can be felt at the Williamstown Farmers' Market, where local vendors graciously welcome tourists to sample fresh, locally grown produce. Meanwhile, those who've caught the adventure bug can head outdoors and explore a 180-acre preserve with boundless recreational opportunities at Mountain Meadow Preserve.
Whether you plan to experience the rich art scene in North Adams or explore Revolutionary War lore in Concord, these overlooked towns in Massachusetts offer their own special spin on the unique New England charm. They are a reflection of the character and resilience that define the region, where industrial pasts are reborn through creativity, and historic moments still echo in quiet streets and verdant landscapes. Visiting them feels like stepping into a different time dimension that is tranquil, authentic, and deeply meaningful.
