10 Quirkiest Massachusetts Towns To Visit In 2025

Massachusetts has its share of stately commons and postcard-perfect towns, but skip Boston and some of the biggest tourist traps in America, and you'll find that this state starts to get quirky. We're talking museums inside old churches, fairy houses in the woods, trails lined with dinosaur footprints, and historic inns with ghost problems. These places are where local lore takes the wheel and the oddities are part of the charm. Whether you're into haunted mansions, antique toy empires, or bridges that bloom, there's no shortage of unique Massachusetts towns you can visit in 2025.

Salem

Salem may be on the larger side as far as Massachusetts towns go, but it's almost definitely one of the most unique. The city of just under 50,000 is famous for its 1692 witch trials, a history that still shapes its character today. Visitors can explore the Salem Witch Museum, which offers detailed exhibits about the trials and their impact. For a different kind of curiosity, the Peabody Essex Museum features an eclectic collection of art and maritime artifacts, reflecting Salem's rich trading history. Outdoor lovers can stroll along the Salem Maritime National Historic Site, where preserved buildings and waterfront views give a glimpse into early American life. Then there's the Salem Willows Park, a classic seaside experience with arcade games, picnic spots, and ocean views, blending old-school fun with the town's eerie vibe.

Winchendon

Winchendon doesn't just have a small-town vibe; it has a giant rocking horse. Clyde, the 12-foot-tall wooden horse standing near the Winchendon History and Cultural Center, is a nod to the town's 19th-century nickname: "Toy Town." That same center also features rotating exhibits on local industry and life, including a collection of handcrafted toys from the area's manufacturing heyday. For those who like their antiques with a side of different, Toy Town Stained Glass and Antiques offers everything from secondhand tools to custom-made windows. This Massachusetts town has something for outdoor lovers, though it's not nearly as quirky. Lake Dennison Recreation Area, just west of town, has hiking trails, swimming spots, and campsites across over 121 acres of land.

Groton

Oddities are tucked between colonial stone walls and rolling conservation land in the town of Groton. At the Groton Inn, one of the oldest operating inns in the United States (rebuilt after a 2011 fire), Revolutionary War ghosts reportedly come with your room key. At least, that's what local legends say. A few streets over, the Lost Lake area has piney trails and an interestingly shaped shoreline, perfect for canoeing or fishing. Cap it off with a visit to Gibbet Hill Grill, where you can hike to castle ruins before your steak arrives.

Shelburne Falls

Shelburne Falls is where a bridge blooms literally every spring. The town's most famous landmark, the Bridge of Flowers, used to carry trolleys across the Deerfield River. Now it's packed with tulips, dahlias, and strangers squeezing past each other for the perfect photo. Just down the hill, you'll find the glacial potholes: huge, swirling rock formations carved by ancient whirlpools. Locals swear they look like lunar craters. For something indoors, the Shelburne Falls Trolley Museum lets you ride a fully restored 1896 trolley car. And if you time it right, Pothole Pictures turns the old Memorial Hall into a part-time theater with indie flicks and live performances.

Holyoke

Volleyball and dinosaurs; the sport and species are separated by more than 65 million years, but both find a home in Holyoke, Massachusetts. The town is the birthplace of volleyball and home to the International Volleyball Hall of Fame, where you can find everything from Olympic jerseys to vintage leather balls that look more like medicine balls. It's also home to the Dinosaur Footprints Reservation, an eight-acre property where visitors can view hundreds of prehistoric tracks preserved in sandstone slabs. Some of these prints are over 200 million years old. More fossilized footprints can be found at the Wistariahurst Museum, although the space also offers tours of a Victorian-era mansion once owned by a silk baron. Even the town's old canal system, originally built to power paper mills, now serves as a scenic backdrop for downtown walks, photo ops, or paddleboarding.

Medfield

Medfield looks like a typical small town in Massachusetts until you realize it has an abandoned psychiatric hospital where Leonardo DiCaprio once filmed "Shutter Island"; the Medfield State Hospital is one of the central attractions in this offbeat town. The complex itself is open for self-guided tours and features 58 separate buildings across a sprawling property. Another major attraction in Medfield is the Vine Lake Cemetery, which can be traced back to 1651. But if macabre is not quite your thing, you can enjoy a gentle hike up to Noon Hill, a 370-foot hill in the middle of a 200-acre reservation. Then there's the downtown area, which is preserved as a historic district and features an assortment of local institutions such as Zullo Gallery and the First Baptist Church.

Sturbridge

Old Sturbridge Village is the centerpiece of Sturbridge, Massachusetts. It's a living history museum where visitors return to the 1830s through restored buildings and hands-on demonstrations of early American life. History continues to echo at the Publick House Historic Inn, a colonial-era tavern welcoming guests since 1771. Nature lovers can explore Wells State Park, which includes over 1,400 acres of absolutely beautiful hiking trails. You can also horseback ride and cross-country ski, depending on the season. When hunger strikes, B.T.'s Smokehouse is a local favorite for slow-smoked brisket cooked with apple and hickory wood, a unique taste in the area.

Ware

An industrial past is worn like a badge in the town of Ware. Once a booming mill town, it's now a time capsule of red-brick factories, vintage storefronts, and a Romanesque town hall that looks like it belongs in a Wes Anderson film. A stone's throw away is the Ware-Hardwick Covered Bridge, an old wooden structure that's a local landmark and dates back to 1886. Then there's the serene and beloved Quabbin Reservoir, a popular place for fishing, hiking, and enjoying breathtaking views. Downtown Ware feels alive in Workshop13 and the ArtWorks Gallery, where local painters, potters, sculptors, and mixed-media artisans display their work. The town thrives on contrasts, proudly embracing its rougher roots while ushering in a newer age of art and elegance.

Concord

Concord is almost definitely known for the Minutemen and transcendentalists, but it's also home to a few corners that history class likely didn't cover. Near Walden Pond, there's the Brister Freeman Homesite, named for a formerly enslaved man who once lived off the land here and counted Henry David Thoreau as a neighbor. The Wayside, a well-worn colonial home once shared by Nathaniel Hawthorne and Louisa May Alcott, still leans ever so slightly on its frame. And if you're craving context, the Concord Museum pulls it all together, from muskets and manuscript pages to Paul Revere's lantern. But if history isn't your thing, Concord has some magic, too. Tucked into the Hapgood Wright Town Forest is a trail fitted with handmade fairy houses, tiny doors, mossy rooftops, and little twig fences.

North Adams

North Adams is a town that thrives on reinvention. It was once an industrial hub and has since transformed into a haven for history, art, and the unexpected. At the heart of its transformation is the Massachusetts Museum of Contemporary Art, which is housed in a labyrinthine complex of repurposed 19th-century buildings. The museum showcases large-scale installations and exhibits. But not everything here is highbrow. Like other Massachusetts towns, North Adams also has a touch of the supernatural. Specifically, the Houghton Mansion. This late 19th-century residence is rumored to be haunted, with tales of ghostly apparitions and mysterious occurrences adding an eerie touch to this town's historic narrative. Once you're done with the indoors, venture outside to explore some of North Adams' most naturally beautiful spots, such as the Cascade Waterfall and Natural Bridge State Park, which is home to North America's only natural white marble arch.

Massachusetts may be known for its Revolutionary roots and Ivy League polish, but it's also packed with towns that proudly wear their eccentricities. In Salem, history gets spooky; in Shelburne Falls, a trolley bridge blooms with flowers, and Winchendon literally rocks its weirdness with a 12-foot wooden horse. These aren't just places on a map; they're living proof that small towns can be as offbeat as they are unforgettable. More than anything, they are certainly worth a visit in 2025.