10 Of The Most Eccentric Towns In Massachusetts

Massachusetts is known as the Bay State, with dozens of inviting coastal towns and popular upscale destinations, including Martha’s Vineyard, Nantucket, and The Berkshires. Its inland parks encompass the scenic mountains of the Appalachian Trail from Mount Everett in the south to Mount Greylock in the north. Massachusetts offers diverse travel experiences for road trips, weekend getaways, or even weeks of intriguing travel.

However, Massachusetts also offers less conventional destinations for those drawn to the unusual and intriguing. Discover 10 of the most eccentric towns in Massachusetts.

Gloucester

Gloucester is located on lovely Cape Ann. Its picturesque setting is an unlikely place for quirkiness, yet it certainly fits the bill. Gloucester is the oldest seaport in America, offering an unsettled and storied history.

Gloucester's Italian-American community continues to practice a time-honored tradition at the St. Peter Fiesta. Known as the Greasy Pole, sailors of all ages test their luck navigating a greasy 40-foot pole extending 25 feet above the ocean. Their goal? Capture the flag. The pole is greased with various slippery substances, increasing the odds of plummeting into the brine.

The Commons Settlement once offered a haven for early settlers escaping pirates and Native Americans in the 1600s. Once the families returned to the shores of Gloucester, the abandoned homes became a refuge for suspected witches and questionable characters into the mid-1800s. Dogs also sought refuge among the outcasts, earning the name Dogtown. Today, the ghost town’s cellar holes are all that remain of the original homes.

Eccentric millionaire Roger Babson catalogued the cellar holes in Dogtown and paid masons to carve the cellar numbers into nearby stones. He also commissioned boulder carvings of old adages along the trails of Dogtown. Known as the Babson Word Rocks, hikers enjoy spotting the quotes along the way.

And speaking of eccentrics, Hammond Castle Museum is a castle built by Thomas Edison protégé John Hays Hammond Jr. Although the castle features a full-on medieval drawbridge, secret passageways, and a lovely garden room in the courtyard, nothing compares to the medieval castle’s eight-story-high pipe organ and massive stained-glass windows in the Great Room.

Lincoln

While most people have heard of Stonehenge, very few have heard of Ponyhenge. Located in Lincoln, just outside of Boston, the playful collection of painted metal and plastic ponies on Old Sudbury Road is rumored to have started with a single hobbyhorse, triggering a growing herd of ponies. The landowners have no quarrel with the whimsical sight, and they welcome new additions whenever they mysteriously appear.

Walter Gropius, founder of the famed German design school Bauhaus, built his extraordinary family home in Lincoln in 1937. The revolutionary design is striking against the New England landscape, inviting visitors to tour Gropius House in all its modernist splendor.

deCordova Sculpture Park and Museum is a large-scale open-air museum featuring a collection of contemporary sculptures and installations. As the largest park of its kind in New England, the diverse collection of over 60 works is constantly evolving. Although the inside galleries are under renovation, the outdoor exhibits span over 30 acres of beautifully landscaped grounds along the shores of Flint’s Pond year-round.

You can also visit the site marking the end of Paul Revere’s heroic midnight run, where he was captured by British soldiers. Although it is nothing more than a monument, it marks a momentous event in American history.

Holyoke

Holyoke’s peaceful setting tucked between the Connecticut River and the Mount Tom Range is classic Massachusetts. However, it has some offbeat attractions that make it a bit enigmatic.

The Frog Circus at Wistariahurst is the work of Naturalist Burlingham Schurr. The whimsical display of frogs is over 90 years old and first appeared at the Holyoke Museum in 1927. Schurr’s goal was to educate youth on the wonders of nature and wildlife, and today the exhibit is a popular curiosity at the 19th-century mansion and gardens at Wistariahurst.

The annual “Great Holyoke Brick Race” races bricks on wheels down an inclined track. Although the fastest machine is a winner, the brick racecars are also judged on “creativity and the sculptural quality” of the car’s design.

At the top of Mount Nonotuck, in the picturesque Mount Tom State Reservation, sits the burned-out remains of the Eyrie House Hotel. In 1901, an accidental fire sparked by a horse cremation set the entire forest and hotel ablaze. The hotel ruins and the foundation of a new hotel, never completed, create a haunting picture in the silent forest.

Just a few miles away are the first fossil dinosaur footprints ever scientifically described. Discovered in 1802, the Dinosaur Footprints in Holyoke are marked in sandstone in the very place these prehistoric animals roamed millions of years ago.

Shelburne Falls

Shelburne Falls is a charming historic village along the banks of the Deerfield River. Known as Massachusetts’ cultural district, the village’s quirky attractions are conveniently located in the heart of downtown.

At the base of Deerfield River’s Salmon Falls is the geological wonder known as Glacial Potholes. Over 50 of these natural sculptural rocks began forming over 14,000 years ago and include the world’s largest known pothole, spanning 39-feet. Also known as kettles, the holes are the result of grinding caused by eddying waters and round boulders. The holes continue to form today.

Shelburne Falls is also home to the only flower bridge in the world. When the charming arched trolley bridge was abandoned in 1928, the weedy overgrowth was a troubling sight for homeowners overlooking the bridge. Antoinette Burnham decided that if weeds could grow there, so could flowers, and the Bridge of Flowers was born. Today, the bridge is abloom with over 500 species from April through October.

You can also ride on Shelburne Falls & Colrain Street Railway trolley car No. 10, the very trolley that rode across the Deerfield River on what is now the Bridge of Flowers. Lastly, Conway Street’s RiverWalk Mosaic Project displays intricate mosaic artworks telling stories inspired by local wildlife, history, and artistry.

Danvers

Although Salem gets all the attention when it comes to Massachusetts’ witch trial infamy, it all started in Danvers. Originally known as Salem Village, Danvers has none of the fanfare you find in Salem, but a few significant historic sites give the town some eccentric street cred.

Salem Village Parsonage is where it all began. The remains of the home of Samuel Parris are nothing more than a collection of stones. However, it sends shivers down one’s spine knowing that the unexplained behavior of Parris’ daughter, Betty, and niece, Abigail Williams, triggered the fear and tensions that led to the mass hysteria of the witch hunts.

The Rebecca Nurse Homestead is the only tourable home once owned by a victim of the Salem Village Witchcraft Hysteria of 1692. It was occupied by the Nurse family from 1678 until 1798 and sits on 25 of the 300 acres the Nurses once owned.

Just down the street stands the Endicott Pear Tree, planted sometime between 1630 and 1649. The tree is believed to be the oldest living cultivated fruit tree in North America and now has the status of a national landmark.

The Salem Village Witchcraft Victims Memorial is an imposing monument across from the town meeting house where the witch examinations first occurred. Although the building is privately owned, the large monument is open to the public. The granite Bible box and book surrounded by shackles is aptly designed to honor the 25 innocents who died at the hands of mass hysteria. The quotes of the accused sit on large granite slabs as a chilling testament to their innocence.

Concord

Concord’s history is tied to America’s transcendentalist movement that shunned societal norms in favor of individualism. That puts it high on the list of eclectic villages. Writer Ralph Waldo Emerson was key to the movement and contributed to many of Concord’s historic sites, including Sleepy Hollow Cemetery.

Sleepy Hollow Cemetery’s Author’s Ridge is a peaceful plot of graves of some of America’s most renowned writing talents, including Mr. Emerson, Henry David Thoreau, Nathaniel Hawthorne, Louisa May Alcott, and William Ellery Channing. Strolling the cemetery and reading the notes left by admirers is a soulful experience.

The Concord Museum is built on a plot of land on the Emerson apple orchard and features Emerson and Thoreau relics, including Thoreau’s desk. The Old Manse is the former home constructed for patriot minister William Emerson, overlooking the North Bridge. Both Ralph Waldo Emerson and Nathaniel Hawthorne called the Manse home, and Henry David Thoreau planted a vegetable garden to mark Hawthorne’s wedding.

Orchard House is the home of "Little Women" author Louisa May Alcott. Considered the “daughter of the Transcendentalists,” she lived in the home with her family. Her drawings remain on the walls, where her parents encouraged her to express her talent when they were too poor to afford art supplies.

Ipswich

Located where the Ipswich River feeds into Ipswich Bay, this coastal town is known for its ocean views more than its eccentricity. However, as home to the backdrop for two cult favorite movies, the kitschy Witches of Eastwick and creepy Flowers in the Attic, the town does have its offbeat side.

Crane Mansion on Castle Hill is a 1928 Stuart-style seaside estate with expansive, landscaped gardens and 59 rooms. Avid 1980s movie fans will recognize the impressive historic landmark and get a kick out of the tour. The back patio’s black griffin sculptures by Paul Manship overlook the ridiculously long lawn, carrying your eye to the ocean beyond. For those unfamiliar with the sculptor, his work includes the golden Prometheus statue at Rockefeller Center.

Many of Ipswich's charming bridges are tied to infamy. The Choate Bridge stands as the oldest documented two-span masonry arch bridge in America. The town contested payment for Warner’s Bridge in 1832, ending in a Supreme Court loss. However, despite the controversy, the bridge designs are lovely historic landmarks worth exploring.

A canoe ride along the river is one of the best ways to discover the town’s history as you slip under the rock bridges, skim the same waters where the Lathrop Brothers Coal and Ice Company harvested ice from the frozen river, and disembark at Ipswich River Wildlife Sanctuary to explore the scenic trails.

North Adams

North Adams sits at the northern edge of the Berkshire Hills with the rolling Green Mountains of Vermont to the north. When it comes to picturesque, some might say this lovely town is unmatched. However, despite its breathtaking natural surroundings, North Adams also has an offbeat side.

The Gunnar Schonbeck Exhibit at the Massachusetts Museum of Contemporary Art (MASS MoCA) is a collection of over 200 handmade instruments designed for anyone to experience the joys of music-making. This interactive experience is a marvel, indulging Schonbeck’s vision that anyone can be a musician and anything can become an instrument. His eclectic mix of instruments made with unconventional materials and designs proves his philosophy. The sounds of his vision come to life with experimental music.

Schonbeck is not the only North Adams resident inspired by sound and music. Artists Bruce Odland and Sam Auinger created the Harmonic Bridge near MASS MoCA. The art installation creates a humming sound from Route 2 overpass traffic. Two 16-foot-long resonating tubes create the sound, delivering an undulating hum in the key of C, creating an unexpectedly soothing resonance that mesmerizes passersby.

With such beautiful surroundings, one cannot visit North Adams without experiencing its natural splendor. Natural Bridge State Park’s white marble arch is the only one of its kind in North America. The 13,000-year-old bedrock marble spans Hudson Brook and the 60-foot gorge carved by glacial erosion. You can also visit an abandoned marble quarry and a man-made white marble dam at the park.

Oak Bluffs

Seaside town Oak Bluffs sits on the northeastern shore of Martha's Vineyard. Although Martha’s Vineyard is known as a bougie sort of place, Oak Bluffs has a far more whimsical side thanks to the colorful gingerbread houses at what was once a Methodist campground.

The Gingerbread Houses of Oak Bluffs are the former cottages of an 1800s Methodist gathering place once known as Wesleyan Grove or Cottage City. This little section of the island owned by the Martha's Vineyard Camp Meeting Association bears witness to over 160 years of history. The lovingly preserved Victorian cottages reflect the commitment of generations of cottage owners.

At the heart of the community is the magnificent Iron Tabernacle, built in 1879. The unique cast iron structure is the work of cottage owner J. W. Hoyt and is an example of inventive 19th-century architecture. The rare wrought iron structure is one of the few remaining buildings of its kind.

The Flying Horses Carousel is a 1884 treasure and the oldest platform carousel in America. The delightful work of Charles Dare of New York Carousel Manufacturing is a rare example of a period carousel. The exceptional craftsmanship is noted in every detail, from the colorful hand-carved wooden horses to the horsehair manes and tails, the glass eyes, and the intricate tufted “chariots.”

Great Barrington

Great Barrington’s scenic Monument Mountain, Mount Everett, and Housatonic River attract nature lovers and outdoor adventurers eager to explore thousands of acres of majestic state forest. However, the quaint historic downtown has a little attraction not often mentioned as a destination for visitors, The Newsboy Statue.

The plucky lad stands eternally in mid-motion, announcing the latest news of the day. As a present to the town in 1895, the boy stands, paper in hand, despite over a century of abuse and natural perils. Set upon an impressive column and kept company by a lion’s head spouting water, the statue is the gift of summer resident Col. William L. Brown, a former teacher and part-owner of the first New York Daily News. The quirky monument also features water fountains to cool down local cats, dogs, horses, and humans.

American historian and the most important early Black protest leader in America, W.E.B. Du Bois, was born in Great Barrington. Discovering his amazing efforts, contributions, and commitment to enriching the lives of Black Americans is an essential part of the town’s history. The W.E.B. Du Bois Center for Freedom and Democracy shares the story of his life and the legacy of his impact on civil rights. The Great Barrington Walking Tour takes you to sites significant to his life, with signage telling his story along the way.

Mr. Du Bois was also an activist for preserving the beauty of the area, and the W.E.B. Du Bois River Park includes a garden and trail steps from his birthplace. A walk along the Housatonic River connects you with his urgings to preserve the river in 1930, “restore its ancient beauty, making it the center of a town…”

The perfect mix of natural and manmade attractions infuses these towns with a good balance of offbeat rituals, a soupçon of infamy, and just enough natural anomalies to pique the interests of the curious traveler.

Whether you love the intrigue of the darker side of history, delight in the whimsical and kitschy, or are inspired by the wonders of nature, these 10 eccentric Massachusetts towns appeal to the edgy traveler looking for unexpected twists.