Hanging greenery on the Buckland Side of the Bridge of Flowers in Shelburne Falls, Massachusetts.

7 Weird Little Towns In Massachusetts

Massachusetts is easy to picture, from its welcoming New England charm and extensive Revolutionary War heritage to its sumptuous seafood cuisine. But behind this seemingly perfect facade lies a collection of communities that proudly embrace their quirks and oddities with no apologies. These reveal a hidden side of the state, full of whimsically oversized roadside installations, unusual traditions, haunted attractions, and further peculiarities.

Unlike your everyday tourist destinations, these offbeat locations demonstrate to visitors the unexpected joys of strangeness while triggering your wildest imagination. From reliving a dark past of unchecked persecutions in Salem to following in the fossilized footprints of a dinosaur in Holyoke, here are weird little towns in Massachusetts you need to visit.

Salem

Scary Halloween house decorations in Salem, Massachusetts. Halloween is year-round in Salem, Massachusetts. Editorial credit: Terry Kelly / Shutterstock.com.

Salem is the poster child for eccentricity among the small towns in Massachusetts, synonymous with the historically infamous Salem Witch Trials. The town compels tourists to relive its days of religious extremism with a fair share of related monuments and historical markers, such as the Witch House. This 17th-century home has a direct connection to the persecutions in Salem, having served as the residence of Judge Jonathan Corwin, who presided over the trials. Today, it is a museum and a critical portal to the past, portraying life in the community during the 17th century.

The Witch House, Salem, Massachusetts.
The Witch House, Salem, Massachusetts.

Furthermore, the Burying Point preserves the graves of trial victims and Revolutionary War casualties, renowned for being a notable haunting site. But Salem has no shortage of oddities beyond the witch trials. Count Orlok's Nightmare Gallery intrigues visitors with its dozens of hyper-realistic wax sculptures of demons, zombies, vampires, and werewolves, created using Hollywood-level special effects.

Medfield

 Lee chapel and research building in Abandoned Medfield State Hospital, a former insane asylum. Lee Chapel and Research Building, part of the abandoned Medfield State Hospital. Image by Yingna Cai via Shutterstock.

Medfield is a small borough in Norfolk County with a rich historical heritage and a dark reputation, often associated with the operation of the Medfield State Hospital. Established in 1892, this former asylum gained infamy for its brutal treatment methods, which led to the deaths of numerous patients. Today, these disturbed spirits are said to roam the hallways, making the building one of the most haunted places in New England. The location has also been featured in Hollywood movies, including Shutter Island and Knives Out.

The Main Street in Medfield, Massachusetts. The Main Street in Medfield, Massachusetts. Editorial credit: Wangkun Jia / Shutterstock.com.

Medfield has a vibrant arts community, with plenty of hubs to inspire budding artists and performers, including the Bellforge Arts Center. Meanwhile, it is surrounded by lush natural spaces that invite outdoor exploration. Ardent hikers are free to explore the 4.5-mile trail system crisscrossing the Noon Hill Reservation for their recreation.

Sturbridge

Two costumed historians work alongside each other inside the tin shop at Old Sturbridge Village, Sturbridge, Massachusetts.Two costumed historians work alongside each other inside the tin shop at Old Sturbridge Village, Sturbridge, Massachusetts. Image by iamroachphoto via Shutterstock.

Sturbridge is a gem in Worcester County that takes travelers on a once-in-a-lifetime journey through time, offering a unique glimpse of life in old New England. The town is famous for hosting the Old Sturbridge Village. This living history museum spans 200 acres and features a collection of antique buildings, artifacts, and a working farm that portrays rural life in New England during the early 19th century. It even features costumed performers and reenactors to enhance the authenticity of the experience for visitors.

Haystacks at Old Sturbridge Village in Sturbridge, Massachusetts.
Haystacks at Old Sturbridge Village in Sturbridge, Massachusetts. Image by Arthur E Gurmankin via Shutterstock.

Meanwhile, outdoor enthusiasts are spoiled for choice when considering a place for their recreation, thanks to the numerous park areas in Sturbridge. Wells State Park offers a 1,400-acre waterfront playground featuring over 10 miles of scenic trails, numerous campsites, and designated fishing zones. Lastly, the friendly townsfolk invite newcomers to join them for a pint of locally crafted beer in the cool atmosphere of Altruist Brewing Company.

Holyoke

Dinosaur footprints in Holyoke, Massachusetts.
Dinosaur footprints in Holyoke, Massachusetts.

Holyoke is a picturesque borough in Hampden County, framed by the glistening waters of the Connecticut River and the undulating landscapes of the Mount Tom Range. It is an excellent escape for outdoor enthusiasts, offering them a rare chance to witness prehistoric fossil treasures at Dinosaur Footprints. The site covers around 8 acres and features dozens of footprints by smaller and larger dinosaurs, believed to date back millions of years.

Holyoke Heritage State Park in Holyoke, Massachusetts.Holyoke Heritage State Park in Holyoke, Massachusetts.

Besides the footprints, guests can have a blast immersing themselves in outdoor adventure. Thanks to Mount Tom State Reservation, visitors have easy access to a four-season recreational playground that supports numerous activities, including hiking, cross-country skiing, biking, and nature photography. Additionally, visiting families can look forward to delightful memories at the Children's Museum of Holyoke.

Shelburne Falls

Glacial potholes in Shelburne Falls, Massachusetts.
Glacial potholes in Shelburne Falls, Massachusetts. By Lisa T Snow / Shutterstock.com

This easygoing community of Franklin County is known for its rich history and stunning outdoor scenery. However, it is also home to a geological treasure that attracts curiosity from within and outside the state. The Shelburne Falls Potholes are a fascinating collection of glacial potholes, ranging in diameter, believed to have formed over 10,000 years ago. It is the largest cluster of natural potholes in the region and resembles something out of a science fiction movie.

Overlooking Shelburne Falls, Massachusetts, with the Bridge of Flowers in the foreground.Overlooking Shelburne Falls, Massachusetts, with the Bridge of Flowers in the foreground.

Shelburne Falls is also home to the Bridge of Flowers, which impresses guests with its display of colorful flowers and views of the Deerfield River, perfect for a lazy stroll. Meanwhile, outdoorsy guests can find numerous opportunities at High Ledges Wildlife Sanctuary. Spanning over 500 acres, it features moderate hiking trails set in a peaceful environment.

Yarmouth

Real gold coins in a treasure chest from the Whydah Galley.
Real gold coins in a treasure chest from the Whydah Galley.

Yarmouth is a stunning coastal community on Cape Cod, just over an hour from Boston, renowned for its sand-swept beaches and beautiful ocean views. However, it also boasts a rich maritime heritage, evidenced by the Whydah Pirates Museum. Claiming to be home to the world's only certified pirate treasure, the museum offers a rare glimpse into the world of piracy in the 18th century. Guests can explore a peculiar collection of artifacts and relics recovered from a vessel used for the slave trade and later for piracy.

Seagull Beach in Yarmouth, Massachusetts.Seagull Beach in Yarmouth, Massachusetts.

Yarmouth also invites vacationers for a taste of beachside art at the Cultural Center of Cape Cod. This family-friendly hub mixes musical, artistic, and culinary experiences to excite guests. Finally, don't miss out on the sandy beaches in town. You can enjoy a leisurely walk on Seagull Beach and revel in the magical scene.

Sheffield

The Historic Upper Sheffield Covered Bridge by Thom Reed UFO Monument Park.The Historic Upper Sheffield Covered Bridge by Thom Reed UFO Monument Park.

Sheffield is a laid-back rural borough in the Berkshires, surrounded by agricultural lands, mountain vistas, and a wide river valley. The town offers lovely outdoor experiences, but the rarest of them all awaits at Thom Reed UFO Park. This private monument commemorates a historically significant UFO sighting and abduction event, the veracity and weight of which has been the subject of town debate for decades. The incident occurred on Labor Day in 1969, with more than 250 people reporting a UFO sighting in the area, making it a significant attraction for alien enthusiasts and conspiracy theorists.

Sheffield, Massachusetts. Sheffield, Massachusetts. Editorial credit: Richard Cavalleri / Shutterstock.com

Sheffield's wide-open spaces support a range of fun adventures, including hiking, camping, picnicking, and wildlife watching across the 329 acres of Bartholomew's Cobble Reservation. Historians can also take a step back in time by visiting the Ashley House. Constructed in 1736, it is among the oldest structures in Berkshire County and has links to slavery in the region.

From the ghostly activities in Medfield to the real pirate treasures in Yarmouth, these peculiar towns in Massachusetts invite you to trade their postcard-perfect reputation for something far stranger and more thrilling. Here you'll discover haunted streets, curious museums, and coastal hideaways where history and eccentricity collide. For those willing to wander off the beaten path, these seven towns offer something far richer than the standard vacation experience, exposing the wonderfully weird underbelly of Massachusetts.

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