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Massachusetts attracts attention for its colonial history, prestigious universities like Harvard, and the bustling city of Boston. But some towns break the mold and take unexpected forms. These unconventional towns promise something different, from quirky annual celebrations to landmarks you won鈥檛 find anywhere else.

Over in Gloucester, the St. Peter's Fiesta draws daring participants to the legendary greasy pole contest. Meanwhile, Newburyport revives classic traditions with the Yankee Homecoming Festival. If you are looking for an adventure beyond the ordinary, these ten towns in Massachusetts should be on your list.

Salem

Salem is unlike any other town in Massachusetts, and its identity was built on the infamous Salem Witch Trials of 1692. The Salem Witch Museum brings the trials to life through exhibits inspired by the real incidents, while the Witch House is the only remaining structure directly tied to the trials. Furthermore, the Witch Trials Memorial serves as a solemn reminder of the hysteria that once gripped the town.

Additionally, every October, Salem becomes the Halloween capital of the country. Haunted Happenings, a month-long festival, fills the streets with parades, ghost tours, psychic readings, and elaborate costumes. Visitors can experience the eerie atmosphere year-round at the Salem Wax Museum or by taking a candlelit ghost tour through the town's historic alleys.

Shelburne Falls

Shelburne Falls feels like a hidden masterpiece in the Berkshire foothills. Its most eye-catching landmark is the Bridge of Flowers, a former trolley bridge turned into a lush floral walkway that blooms with color from spring to fall. The bridge is operational seasonally between April and October, but it underwent restorations in 2024 (it is expected to reopen in 2025).

About 500 meters away are the Glacial Potholes. These are a series of swirling rock formations carved more than 14,000 years ago by ancient waters, creating an other麻豆AVly landscape unlike anywhere else in Massachusetts. Although swimming is no longer allowed in the area, visitors can take pictures or admire the nearly 50 potholes in the Deerfield River.

Provincetown

Provincetown is the crown of the tip of Cape Cod, where the Atlantic meets a town drawing in artists, writers, and free spirits for over a century. The town's biggest celebration, the Provincetown Carnival, fills the streets into a spectacle of elaborate costumes, dazzling parades, and uninhibited joy. Held every August, this LGBTQ+ festival draws attention to Commercial Street with the parade. Then, there are costume contests, pool gatherings, and even drag events.

Beyond the festivities, the town's dunes hide a piece of living history. The Dune Shacks of Peaked Hill Bars, scattered along the 1,900-acre windswept landscape, once housed writers and painters seeking solitude and inspiration. Some of these historic shacks remain as artist residencies, carrying on the tradition of creative retreats. A guided tour offers a rare chance to step inside these remote hideaways and see the same untouched scenery that influenced greats like Eugene O鈥橬eill and Jackson Pollock.

Rockport

Rockport, a small fishing village on the North Shore 40 miles from Boston, is famed for its deep ties to the arts and the sea. Motif No. 1, a simple red fishing shack inspiring generations of painters and photographers, is the most recognized part of town. It has been called the most-painted building in America. Every May, Rockport upholds this artistic landmark with Motif No. 1 Day, a festival featuring live music, art shows, food trucks, and a lively parade.

While the festival honors tradition, Rockport also surprises visitors with something entirely unexpected: the Paper House. This 1922 structure by mechanical engineer Elis Stenman is a cottage made almost entirely of newspaper, from its walls to its furniture. The pages, glued and varnished to hold their shape, still reveal glimpses of century-old headlines and ads. It is a one-of-a-kind stop that turns a simple material into a work of creativity.

Gardner

For over a century, Gardner, or the "Chair City," was a hub for handcrafted wooden chairs, earning a reputation for fine craftsmanship. That legacy stands tall鈥攍iterally鈥攚ith the "Bicentennial Big Chair," an enormous 20-foot wooden chair that serves as a quirky landmark and a tribute to Gardner's manufacturing past. Originally built in 1905 and later reconstructed, this oversized piece of furniture stands as a reminder of the town's former title as the "Furniture Capital of New England."

Beyond the giant chair, the Gardner Museum brings this history to life. Housed in a former 1800s library, the museum showcases vintage furniture, local artifacts, and rotating exhibits on the town's industrial roots. Visitors can see examples of handcrafted chairs from the town's peak production years and learn about the businesses that shaped Gardner's identity.

Aquinnah

Aquinnah, a quiet community on Martha's Vineyard, strikes out for its breathtaking Gay Head Cliffs. These multicolored clay cliffs rise above the Atlantic, shifting in hues of red, orange, and purple depending on the light. Beyond their natural beauty, the cliffs hold profound cultural significance for the Wampanoag Tribe, who have lived in this area for centuries. Visitors can take in the view from the overlook or walk down to Moshup Beach, where the clay-streaked shoreline meets crashing waves.

Perched above the cliffs is the Gay Head Lighthouse, one of the oldest lighthouses in the country. Originally built in 1799, it has guided sailors for over two centuries. The lighthouse was moved inland in 2015 to prevent it from falling into the sea due to erosion. Visitors can climb to the top for sweeping views of the Elizabeth Islands and Vineyard Sound.

Newburyport

Every summer, Newburyport stands for the Yankee Homecoming Festival, a week-long extravaganza upholding the New England people. The festival dates back to 1958 and includes events like the "Olde Fashioned Sunday," where visitors can appreciate vintage games, classic cars, and local music. The week ends with a grand parade and fireworks over the Merrimack River, making it one of the most anticipated events in the region.

In contrast, Plum Island presents a more subdued side of Newburyport. This barrier island is home to sandy beaches, salt marshes, and the Parker River National Wildlife Refuge, where birdwatchers can spot migrating shorebirds.

Gloucester

Gloucester is among the oldest fishing ports in the United States, and its connection to the sea is at the heart of its culture. The best way to experience Gloucester is St. Peter's Fiesta, a five-day festival to mark the 'patron saint of fishermen.' The event, which started in 1927, brings together locals and visitors for parades, boat races, and band performances. Perhaps the most fascinating affair is the greasy pole contest, where competitors attempt to run across a greased wooden pole suspended over the harbor. It is a test of balance, determination, and sheer will, making it one of the most unusual competitions in New England.

Gloucester鈥檚 identity is tied to its fishermen in more ways. The Man at the Wheel statue, otherwise the Fisherman's Memorial, stands along Stacy Boulevard, facing the harbor. It honors those lost at sea and serves as a powerful reminder of the town鈥檚 history. Nearby, the Fishermen鈥檚 Wives Memorial recognizes the families who waited for loved ones to return.

Oak Bluffs

Oak Bluffs is a beautiful 麻豆AV apart, with its vibrant Victorian cottages and a summer tradition unlike anything else in Massachusetts. Grand Illumination Night, held in the first week of August, converts the town's Gingerbread Cottages into a glowing spectacle. Thousands of colorful lanterns hang from the porches of these tiny, ornate homes, casting a warm light over the Martha's Vineyard Camp Meeting Association. The event first took place in the 1800s to welcome the state's governor to the area, and it has remained a cherished tradition, featuring a community sing-along and a ceremonial first lantern lighting.

Just a short walk from the cottages is another piece of history: the Flying Horses Carousel. It has been the oldest operating platform carousel in the US since the 1870s. The hand-carved wooden horses still have their original glass eyes and real horsehair tails. Riders can try their luck grabbing the brass ring, a tradition that adds to the carousel鈥檚 old-fashioned charm beginning its season in April.

West Springfield

West Springfield may seem like an ordinary town, but once a year, it is the center of New England鈥檚 biggest celebration. The Eastern States Exposition, known as "The Big E," is no typical fair. It is a massive, multi-state event that showcases the culture, food, and traditions of all six New England states in one place. Each state has its own replica building along the Avenue of States, giving visitors a chance to sample Vermont maple syrup, Maine lobster rolls, or Rhode Island clam cakes鈥攁ll without leaving Massachusetts.

The Big E is also packed with attractions. The Giant Slide has been a favorite for generations, while the parades bring in marching bands, floats, and performers. The fair鈥檚 Midway promises classic carnival rides, games, and food, including the famous Big E Cream Puff. Livestock competitions, craft exhibits, and live music performances make it more than just a fair鈥攊t is a cultural experience.

Massachusetts is full of surprises, and these ten unconventional towns prove that some of the most memorable experiences come from the unexpected. Tradition plays a major role in shaping these towns, like witnessing the Grand Illumination Night in Oak Bluffs, where lantern-lit cottages glow under the summer sky. Even the landmarks here feel one-of-a-kind. From quirky traditions to unexpected history, these towns in Massachusetts invite visitors to see through a different lens鈥攐ne filled with wonder, character, and unforgettable moments.