7 Quirkiest Massachusetts Towns You Didn't Know Existed
Massachusetts is renowned for its rich history, charming coastal villages, and vibrant cities. But beyond the well-walked tourist hotspots of Cape Cod, Salem, and Martha’s Vineyard, is a treasure trove of small, quirky towns bursting with character, creativity, and local charm. From towns with vibrant art scenes, like Williamstown, to distinctive landmarks like Berkley, and those with deep musical roots, like Lenox, these hidden gems offer visitors a chance to experience authentic New England culture with a unique twist. Whether you’re exploring a floral-covered bridge, hiking through the forest, or wandering historic streets lined with indie bookshops and used record stores, here are seven of the quirkiest Massachusetts towns you didn’t know existed.
Shelburne Falls
The pretty village of Shelburne Falls sits along the Deerfield River in the scenic Pioneer Valley in the foothills of the Berkshires. First settled in 1756, the town’s economy relied on the water-powered mill that manufactured cutlery and knives. Lamson and Goodnow were the oldest cutlery manufacturers in the U.S. when they were established in 1837. Today, the Lamson Factory Outlet is located next to the mill, which is home to over a dozen artisan shops and makers.
That spirit of transformation flows through the quirky village, which features one of its most-visited landmarks, the Bridge of Flowers—a former 1928 trolley bridge that has been reimagined as a gorgeous seasonal garden path over the river. The original 1896 Trolley Car No. 10 has been restored and is an integral part of any visit to the Shelburne Falls Trolley Museum, where young visitors can play with wooden and electric trains while they wait for the trolley ride. Finally, head to the observation deck in town to view the otherworldly Glacial Potholes, over fifty stunning potholes (or kettles) that range in size from 6 inches to 39 feet, which started forming after the last Ice Age.
Berkley
Berkley is a charming small town, located 35 miles south of the state capital, Boston, making it the perfect day trip to commune with nature. Settled in 1638 and incorporated in 1735, the Massachusetts town and Berkeley, California, were named after an 18th-century Irish bishop and philosopher, George Berkeley. Renowned as the home of a mysterious petroglyph-covered boulder, the 85-acre Dighton Rock State Park invites outdoor enthusiasts to delve into the mystery during a visit to the pavilion museum. The park is also the ideal spot to paddle, fish, or picnic next to the Taunton River.
Listed on the National Register of Historic Places, the Berkley Common Historic District is at the center of town and serves as the community hub for its summer concert series and other events, and features the Old Town Hall, dating back to 1849, a library, and the landmark Berkley Congregational Church established in 1737. On the way back to Boston, stop at the Star Drive-In for a Star Burger, a side of fried Oreos, and tons of 1964-era nostalgia.
Ashfield
Ashfield is a hilly town in the Berkshires surrounded by rolling farmland, woodlands, and several small lakes, perfect for outdoor pursuits like kayaking, swimming, and diving from the dock at Ashfield Lake and nearby Belding Park. Revealing its 18th-century roots, the Ashfield Plain Historic District features well-preserved classic Federal, Greek Revival, and Victorian architecture, as seen in businesses like the recently opened Wicked Good Café, formerly Elmer’s Store, a beloved general store dating back to the 1830s, and Ashfield Hardware & Supply.
The small town, with fewer than 2,000 residents, boasts a vibrant arts and culture scene, anchored by the innovative Double Edge Theatre, an art, community, and cultural collective situated on a 105-acre former dairy farm where artists live, train, perform, and farm. The collective’s annual summer spectacle is held outdoors, a journey across fields, ponds, and barns that invites audiences into the performances.
Erving
Erving is a small river town nestled along the 63-mile-long Mohawk Trail, New England’s first designated scenic road. With the Millers River winding through its town center, Erving offers picturesque views and outdoor adventures like fishing, kayaking, and whitewater rafting. The nearby 2,422-acre Erving State Forest also features lots of opportunities for physical activity, including camping, swimming in Laurel Lake, and eight miles of forest hiking trails, including the one-mile Laurel Loop Trail, which provides a spectacular view of 3,165-foot Mount Monadnock.
Visitors to Erving won’t want to miss the iconic French King Bridge, a graceful steel arch once dubbed the “Most Beautiful Steel Bridge.” The bridge spans the Connecticut River not far from Erving, offering breathtaking views of the surrounding landscape. The bridge takes its name from the nearby French King Rock, which rises prominently in the middle of the river, adding to the mystery of this picturesque site, rumored to be haunted by ghosts. After a day of adventure, stop by the Freight House Antiques & Café, a former functioning freight built in the mid-19th century by the Boston & Maine Railroad, for a bit of antiquing and one of their famous mixed berry scones.
Montague
Another quirky river town in the Pioneer Valley beside the Connecticut and Millers Rivers, Montague is an undiscovered destination for outdoor explorers, art enthusiasts, and especially book lovers. Home of the Montague Bookmill, a used bookstore housed in an 1842 gristmill on the Sawmill River, the beloved store’s slogan is “Books you don’t need in a place you can’t find.” Next door to the book shop, discover the Sawmill River Arts Gallery. This friendly, artist-run gallery showcases a diverse range of work from over 30 local artists and makers, including jewelry, paintings, pottery, and more. Music aficionados will love the local used record shop, Turn It Up!
Montague has over 20 miles of trails to explore on bike, including the paved 3.7-mile Canalside Rail Trail, a former rail trail that skirts along a section of the Connecticut River. Along the trail, riders will discover the nearby Great Falls Discovery Center, an ideal pitstop for exploring the natural, cultural, and industrial history of the Connecticut River watershed. Inside the refurbished old mill, visitors will discover exhibits and diagrams depicting the plants, animals, and landscapes along the 410-mile-long Connecticut River, which originates in Fourth Connecticut Lake in New Hampshire and empties into the Long Island Sound at Old Saybrook, Connecticut.
Williamstown
Williamstown is a charming college town, full of small-town charm and a vibrant cultural scene. Home to Williams College, a private liberal arts college founded in 1793, the campus includes over 100 buildings spread over 450 acres, including the Williams College Museum of Art (MCMA) and its 15,000 works of art, and the iconic Hopkins Observatory. The observatory was built between 1836 and 1838, making it the oldest extant astronomical observatory in the United States, where visitors can stargaze through historic telescopes.
Another worthwhile campus to visit in Williamstown is the Clark Art Institute, or simply The Clark, situated on 140 acres of beautifully landscaped lawns, meadows, and trails. The museum is renowned for its collection of French Impressionist paintings, including works by Claude Monet, Edgar Degas, and more than thirty paintings by Pierre-Auguste Renoir. Wander along the tree-lined streets downtown and stop in at local shops like Tunnel City Coffee, the nickname of the historic Hoosac Tunnel in neighboring North Adams.
Lenox
Lenox is the quintessential Berkshire town, with deep cultural roots, including being the home of the renowned theater company, Shakespeare & Company, and landmarks such as The Mount, author Edith Wharton’s iconic estate; Ventfort Hall, a Gilded Age mansion and museum; and Tanglewood. A National Historic Landmark, The Mount is a turn-of-the-century home, now a house museum, cultural center, and public park, designed and built in 1902 by the Pulitzer-Prize-winning author of “The Age of Innocence.” Ventfort Hall is a 28,000 square foot “cottage” on the National Register of Historic Places. Initially built for the sister of J.P. Morgan, the stunning mansion and gardens are open for self-guided tours.
Finally, Lenox is home to the Tanglewood Learning Institute all year round. Still, it is most famous as the summer home of the Boston Symphony Orchestra, which welcomes 350,000 visitors annually for recitals, seminars, and theater performances. In addition to the concerts by the BSO held in the Koussevitzky Music Shed on campus, the 2025 Summer Tanglewood Popular Artists Series features shows by James Taylor, Emmylou Harris, and John Legend.
These seven quirky Massachusetts towns you didn’t know existed offer a delightful escape into the charm and creativity of small-town New England life. Stroll along riverside paths, browse unique bookstores, fish in a river, or enjoy a re-imagined garden and a quirky landmark or two. These towns invite you to slow down and enjoy towns where funky coffee shops and local markets have replaced old-timey general stores as gathering spots, and cultural gems like theaters and art galleries help keep traditions alive.
