7 Most Eccentric Towns in Massachusetts
Massachusetts may be known for its historic villages and postcard-perfect towns, but sprinkled across the state are seven of the most eccentric towns that proudly celebrate the wacky, the artsy, and the wonderfully weird. From tall granite monuments and hyper-realistic wax figures guaranteed to give you wild dreams to funky coastal villages filled with artists and free spirits to inland towns with quirky house museums, themed rooms, and creative oddities, these seven spots prove that the Bay State has a delightfully offbeat side just waiting to be explored.
Provincetown
With its reputation as a haven for artists, writers, and creatives of all kinds for over a century, Provincetown embraces the wacky and eccentric with open, loving arms. Known to the locals as P-town, this small coastal town of 3,600 residents at the very tip of Cape Cod has a little something for everyone, from the iconic Pilgrim Monument and Provincetown Museum (PMPM) to the 43,500 acres of sandy beaches, marshes, and ponds of the Cape Cod National Seashore. Visit the museum to learn how the first Pilgrims landed in the New World in 1620, and climb the 116 steps and 60 ramps of the tallest all-granite tower in the U.S. for stunning 360-degree views of the seashore, including a view of the capital city of Boston on a clear day. In town, enjoy drinking, eating, and shopping on one of Cape Cod’s dynamic Commercial Street. Don’t leave town with a stop at one of P-town’s most well-loved and photographed institutions, The Lobster Pot.
Salem
Synonymous with eccentric, Salem is a renowned town of about 46,000 residents that really leans into its witchy reputation year-round (especially in October). While you can’t escape the town’s storied reputation of religious extremism, persecution, and injustice, which is impossible to ignore at the dramatic Salem Witch Trials Memorial to the 20 victims of the 1692 witch trials, there’s still a lot of whimsical and wacky fun to be had in Salem. Start at Count Orlok’s Nightmare Gallery, a fantastical monster wax museum full of over 60 hyper-realistic vampires, zombies, werewolves, demons, you name it, created by Hollywood’s best special effects artists.
The Witch House (once the home of Judge Jonathan Corwin, who presided over the notorious trials) is the most famous in town, as the only building still standing with direct ties to the witch hunt. Be sure to snap a selfie in front of its dramatic all-black exterior. If pop culture is your bag, be sure to visit the bronze statue of Samantha Stephens from the wildly addictive 1960s TV show “Bewitched,” for a photo op with the good witch poised with her broom in a crescent moon. For craft beer, zany cordials, and coffee, stop by the Gulu Gule Café, named for a coffee shop in Prague where the owners met.
Northampton
A proudly offbeat, progressive college town with a vibrant arts and culture scene, Northampton is home to Smith College, a prestigious private liberal arts college, which the city of 31,800 residents owes much of its creative energy to. Smith College is one of the “Seven Sisters,” a historic group of elite women’s colleges in the northeastern U.S., as a counterpart to the Ivy League. The college campus is one of the most beautiful in New England. It centers on the Smith College Botanic Garden, spanning 127 acres and featuring the stunning greenhouse complex, the Lyman Conservatory, an arboretum, and numerous outdoor gardens. Explore the 150-year-old college with a stop at the esoteric Mortimer Rare Book Collection in the Neilson Library, which has 17th-century editions by William Shakespeare, and books and manuscripts by both Virginia Woolf and Sylvia Plath, who famously graduated summa cum laude from there in 1955.
Downtown Northampton is full of eclectic shops selling everything from vinyl records and healing crystals to collectibles and vintage clothing. The historic Thornes Marketplace has a vintage photobooth where you can get an old-timey strip of 4 black-and-white photos, and the Hometown Arcade, a retro arcade with classic pinball machines, Skeeball, air hockey, and more.
Rockport
Rockport, Massachusetts, better known as the hometown of Motif No. 1, the little red shack that somehow became a national celebrity, is a small artsy town of 3,600 residents on the rocky shores of Cape Ann overlooking the Atlantic Ocean. Once a thriving art colony, one of the oldest in the U.S., Rockport is still renowned for its concentration of over 30 art galleries and the Rockport Art Association and Museum (RAA&M). For over 150 years, the one-time fishing village’s spectacular setting has attracted some of the most acclaimed artists from the 19th century to the present, and each year the RAA&M celebrates that legacy with more than 40 exhibitions.
Explore Bearskin Neck, Rockport’s main drag, which starts in the center of town, Dock Square, and stretches across town to the harbor and Motif No. 1, where you’ll discover no shortage of one-of-a-kind shops like Carol Lee’s Cottage for curated coastal gifts and the old-timey Bearskin Neck Country Store for penny candies, funky souvenirs, and retro toys.
Shelburne Falls
Nothing captures quirky charm and eccentricity better than a bridge overflowing with thousands of blossoms, which is precisely what you’ll discover in the small village of Shelburne Falls, population 1,700, home of the famous Bridge of Flowers. Open year-round, the hanging garden is a repurposed former trolley bridge that spans the Deerfield River, one of the most beautiful rivers in New England, connecting the towns of Shelburne and Buckland. After exploring the bridge, go full circle with a visit to the Shelburne Falls Trolley Museum and ride the original Shelburne Falls & Colrain Street Railway trolley car No. 10. that once rolled across the bridge.
For old-fashioned throwback fun, try your hand at candlepin bowling at the second-oldest bowling alley in the United States, the 1906 Shelburne Falls Bowling Alley, where you can also enjoy a cocktail or mocktail and listen to live music in the onsite lounge. For book lovers, the town also counts three bookstores among its retail hotspots, including Boswell’s Books and Raven Used Books.
North Adams
The small town of North Adams, population 12,400, is a former mill town turned arts destination, thanks to a giant converted factory turned art space, MASS MoCA (Museum of Contemporary Art). The former Sprague Electric Company operated there from the early 20th century until the 1980s, until it was repurposed in the 1990s into a hub for visual arts, performance, and exhibits. While North Adams claims to be the smallest city in Massachusetts, it is the northern terminus of the Massachusetts section of the Appalachian Trail, the longest continuous hiking-only trail in the U.S.
North Adams is near the summit of Mount Greylock, the highest peak in Massachusetts at 3,491 feet above sea level, where on a clear day, you can look across 90 miles and three states, including Vermont, New York, and Connecticut. At the summit, there’s a striking 1932-built War Memorial Tower that looks like a coastal lighthouse when illuminated at night.
Gloucester
The giant “Man at the Wheel” statue, honoring Gloucester's history as a gritty fishing port, is the town’s most photographed landmark. It’s either that, or Hammond Castle Museum, a medieval-style castle built by inventor John Hays Hammond Jr. in the 1920s. Renowned as an “inventor’s inventor,” Hammond was a brilliant scientist, collector, and all-around eccentric who stuffed his castle full of medieval statues, stained glass windows from European churches, old wooden doors, and much more.
For more unusual architecture, visit the Beauport, the Sleeper-McCann House, the summer home of one of the first professional interior decorators in the U.S., Henry Davis Sleeper. Perched on a rocky ledge overlooking Gloucester Harbor, the house is a collection of glass, china, and folk art distributed across 40 historical or literary-themed rooms, described as a “kaleidoscope of color and curiosities” in this town of almost 31,000 residents. Finish up the day at the harbor at the Seaport Grille, a cozy pub+restaurant serving fresh oysters, lobster rolls, and market clams.
Massachusetts may be synonymous with colonial history, cobblestone streets, and New England charm, but just beneath the surface, you’ll find an eccentric streak running through the state. Beyond the Revolutionary landmarks, lighthouses, and lobster traps are places that revel in the quirky, the artistic, and the delightfully odd. From P-town to Gloucester, these seven eccentric destinations prove that Massachusetts’s weird side is every bit as compelling as its history.
