8 of the Quirkiest Towns in Massachusetts

Within the United States' 50 members, Massachusetts holds a unique position as one of the oldest. During the beginning of European settlement in North America, the state was colonized by Pilgrims at Plymouth. The state was vital during the American Revolution, and was among the inaugural thirteen states that made up the original colonies.

As settlers poured into the United States, interesting and novel places started to pop up over the state. From giant chair statues to gingerbread-style homes, there are a lot of towns in Massachusetts that are odd or distinctive, and certainly one-of-a-kind. Read on and find out 8 of the quirkiest towns in Massachusetts to visit.

Stockbridge

There is a chance you have seen Stockbridge a few times and have never known it. Confused? The town is linked to the iconic American illustrator Norman Rockwell. He immortalized the town in his paintings, using art to depict the heart of simple American life.

Do you know where to find the biggest collection of original artwork by Norman Rockwell these days? Well, no surprise but it is in Stockbridge, at the Norman Rockwell Museum.

"Stockbridge Main Street at Christmas," an acclaimed piece by Rockwell, showcases the main street of the town. Every holiday season, locals bring the painting to life by duplicating what is happening inside the painting, with antique cars and decorations reminiscent of the 50s and 60s era.

Tracing back to its roots to the eighteenth century, The Red Lion Inn has been a key factor in defining Stockbridge. It wears its old-world charm proudly with antique furniture and a house cat wandering about.

For one last local treat, check out the lavish Berkshire Cottages. The structures represent the grand residences constructed by affluent families during America's Gilded Age. These estates reflect America's aristocratic past and are gems amidst the Berkshire landscape.

Newburyport

In the downtown core of Newburyport, on a warm summer's day, the sun lightens the red brick buildings and warms the cobblestone roads.

On the cusp of the Atlantic, a brief 45-minute trip north from Boston, lies a charming town right in the heart of American history. Once a vibrant center renowned for boat-building and global trade, particularly in the 18th and 19th centuries, this town's nautical past is visible at its Customs House Maritime Museum. The museum brilliantly captures the local seafaring stories of merchants, boat makers, and buccaneers.

The town is also chockfull of curiosities to see.

One of them is the Pink House, a petite home with a radiant coating of pink. Its history is linked with stories about a 1920s divorce settlement where supposedly, to vex his former wife, a man constructed this house embodying everything she desired but set inconveniently in a marsh.

Each year Newburyport welcomes the Yankee Homecoming Festival, an event that ranks among America's longest-running homecoming celebrations. The charm comes from its blend of activities such as bed races, parades, and a collection of concerts and events suitable for families.

Salem

Salem gained notoriety from the witch trials of 1692, a time when townspeople went through unfounded allegations and executions on suspicion of being witches. Even though this gloomy occurrence has carved itself into Salem's character, the community accepts its murky past.

When October arrives it ushers in “Haunted Happenings” - a month filled with spine-tingling activities that transform the town into a Halloween haven. From creepy ghost tours and psychic consultations to festive parties, these events mark autumn’s arrival.

A more somber reminder of the town’s past is the Witch Trials Memorial. It is a powerful tribute to the victims of the 1692 trials, with 20 benches coming out from a low stone wall, each with the name of an accused person, the means of execution, and the date of their death.

Salem houses the continually operating Peabody Essex Museum, one of America's earliest museums. They have a unique exhibit there, a 200-year-old Chinese house, which they brought over from China and rebuilt it right inside the museum.

Gardner

Feel like having a seat? Come visit "Chair City." Gardner famously got its quirky name because of its history in furniture production, especially chairs.

This town once had several different chair factories, and its pivotal role in furniture creation during the 19th and early parts of 20th century is part of its essence.

Based on that, it only makes sense that of all places, Gardner is home to the Big Chair, a giant seat that is one of their most famous landmarks. This oversized novelty was built to commemorate their significant role in furniture making.

The chair-based connection gets even more involved. In Gardner, there is a chair in the Levi Heywood Memorial Library said to be haunted. Local legends suggest the chair moves on its own and those who sit in it experience a sense of unease or discomfort.

If you need a break from all these chair-themed attractions, check out Dunn State Park, which has gorgeous ponds and trails to see. Don't worry, it also has some good places to sit, and they are probably not haunted.

Rockport

True to its name, Rockport sits on the rugged and rocky shores of Massachusetts. The nearby coast is lined with granite boulders and cliffs, but also beautiful beaches.

In town, you can stumble across a peculiarly-named land strip named Bearskin Neck. This thin stretch sticks out into the sea from Rockport. Here on this stony outcrop, there are numerous stores, art displays, and seafood shops.

Right on Bearskin Neck lies Motif Number 1, a classic red fishing shack that is one of America’s most painted and photographed structures. This icon perfectly reflects New England maritime culture and has long served as an artistic inspiration for countless creatives.

Also there exists a peculiar attraction named the Paper House, an unconventional structure entirely made from newspapers. Erected back in 1922, not only is the house made of newspapers but even its furnishings are derived from the same material.

Another interesting tidbit about Rockport; it was dry for the majority of its existence. It became a alcohol-free in 1856 and only lifted the ban in 2005, almost 150 years altogether.

Provincetown

Known locally as "P-Town" this town is found up on the tip of Cape Cod, with narrow winding streets not far from beaches and rolling dunes.

The architectural design of the town combines elements from 19th-century New England and Portuguese aesthetics, mirroring its roots as a fishermen's settlement and the impact made by Portuguese immigrants.

Also among the shifting sands of Cape Cod National Seashore, you can find "dune shacks" to stay in. For a long time, artists and writers have come to use the shacks in an effort to get inspiration.

For generations, Provincetown has been a beacon for writers, artists and actors. Its offbeat bohemian energy fuels its vibrancy.

Its artistic legacy is mirrored by the host of galleries along with institutions like the Provincetown Art Association and Museum. Huge personalities including Norman Mailer and Tennessee Williams found solace here either residing or seeking peace and quiet.

Within the town limits, guests can see the towering Pilgrim Monument, America's highest all-granite structure. This monument serves as a reminder of the Mayflower Pilgrims' initial touchdown in Provincetown back in 1620, prior to their relocation to Plymouth.

Shelburne Falls

As you stroll about Shelburne Falls, your eyes will be drawn to a bridge that looks like nature took over.

Once a passage for trams, the Bridge of Flowers underwent a metamorphosis in the 1920s. It came out as a flourishing covered expanse, with flowers and lush plants. It is one of only a few bridges of its kind in the world.

That is not the only curioius connections to bridges around town. Every year, the town holds a dinner on the Iron Bridge, which spans the Deerfield River. At the annual Iron Bridge Dinner, you can find great local food and communal dining, all with the background of the peaceful river nearby.

The town has some very interesting geological history right in its borders, and is home to a collection of glacial potholes. Approximately 14,000 years ago, on the tail end of the last Ice Age, these imprints began to form in Shelburne Falls.

Currently, the town has approximately 50 potholes, the biggest of which is named the "Salmon Hole." This mammoth pothole is amongst the largest on the planet, boasting a diameter of about 39 feet.

Oak Bluffs

Oak Bluffs, found on Martha's Vineyard in Massachusetts, is famously recognized for its rare Victorian "gingerbread" style buildings.

The town is home to the oldest continuously operating platform carousel in the United States. Established in 1876, the Flying Horses Carousel stands as more than just a cherished local landmark, it is also an identified National Historic Landmark.

With its vintage horse figures and brass ring game, this carousel offers visitors a one-of-a-kind trip down memory lane.

One of Oak Bluff's landmarks made a cameo in a Steven Spielberg movie. The American Legion Memorial Bridge became well-known from a scene in the movie "Jaws." Nowadays, courageous tourists sometimes leap off into the water beneath, a quirky custom spurred by tradition due to the film's influence.

Right in town, Ocean Park features broad green stretches and a vintage bandstand and is a pleasing spot overlooking the sea. Normally the spot is used for local concerts and social gatherings, a great spot for the community to come together.

In Conclusion

In Massachusetts, each town, from Rockport's iconic red fishing shack to Gardner's giant chair, offers visitors an exceptional slice of Americana.

These places, full of history and brimming with quirky charm, invite visitors to explore their spirit and character.

You can find it at the artistic haven of Provincetown or in the witchcraft lore of Salem; these towns are just sitting there for explorers who want something a little bit less than ordinary.