9 Offbeat Towns to Visit in Vermont

To some, Vermont is one big town. In truth, it is one medium-sized city, several small cities, and around 250 towns, all of which can be considered offbeat. These are the best of the off the beaten path, which boast things like Vermontasaurus, the Bread and Puppet Theater, an ice cream graveyard, the Bennington Triangle, and the ruins of a secret, supergun-creating government laboratory. Learn about these extremely offbeat Green Mountain State attractions and the communities where they can be found.

Northfield

Northfield is a town of 4,000 in verdant Central Vermont. It is known throughout the state for its covered bridges, of which there are five, and its military college, Norwich University. But it is known locally for Pigman. Legend has it that a half-man, half-pig roams the woods around town, particularly near Devil’s Washbowl. A trip to Northfield can take you through the beautiful bridges while you search for Pigman. That search will probably be in vain, though, so you can instead pig out at eateries like Good Measure Pub and The Common Cafe, which serves great pancakes.

Bennington

If you thought the only paranormal triangle is in Bermuda, take a trip to Bennington in Southern Vermont. This 15,000-person town belongs to an area where five people vanished from 1945 to 1950. The "Bennington Triangle," as coined by folklorist Joseph Citro, also comprises the communities of Woodford, Shaftsbury, and Glastenbury. Appropriately, Glastenbury is mostly a ghost town, having deteriorated after a 19th-century timber boom.

Brave tourists can explore the ruins of Glastenbury in the Green Mountains, whose wilderness is to blame for at least some of the disappearances. Return to Bennington for haunts like the Bennington Battle Monument, which commemorates a bloody skirmish from the Revolutionary War, or travel to North Bennington to see the spiritual setting for Shirley Jackson's horror story The Lottery.

Waterbury

You might scream in Waterbury, but not for the reasons you might scream in Northfield and Bennington. You might scream for ice cream, since Waterbury is the home of Ben & Jerry's. Their factory, located in the Waterbury Village Historic District, is open for tours inside and out. Ben & Jerry's operates a Flavor Graveyard with headstones for discontinued pints such as Vermonty Python and This is Nuts. If, by small chance, ice cream is not your favorite, Waterbury has breweries for cider and India pale ale. It also brews beautiful scenery, like what you can see atop Camel's Hump mountain.

Glover

If you love bread, puppets, and everyday life, you should love Glover. This Northern Vermont town of just over 1,000 residents abuts the Bread and Puppet Theater and the Museum of Everyday Life. The former is a performance museum that puts on puppet shows with radical political messages made palatable by complimentary bread and aioli. The latter is a self-guided menagerie of the mundane, where everything from safety pins to toothbrushes to gas cans are displayed with pride. To further celebrate everyday life (including bread), hit up Glover's Busy Bee Diner, one of the cutest and smallest eateries in America.

Proctor

There is one genuine castle in Vermont and it is near the tiny town of Proctor. Wilson Castle, built in the late 1800s for American-English aristocrats, sits on West Proctor Road and hosts tours, parties, weddings, and ghost hunts. Containing European and Asian antiques, Wilson Castle also serves as a museum, as does the Vermont Marble Museum in Proctor proper, which honors the town's marble-harvesting past. Proctor's famous marble was used to construct the Marble Bridge, a National Historic Place over scenic Otter Creek providing the town's east entrance.

Thetford

Ever heard of Vermontasaurus? Head to Thetford to find out more. Sadly, it is not a real dinosaur. It is a 122-foot-long, 25-foot-tall sculpture at Post Mills Airport in Thetford, Vermont. It was built out of scrap lumber by a team led by Brian Boland, a hot air balloon operator who died in his 11,000th airborne hour in 2021. He left his mark not just with Vermontasaurus but with its baby and other smaller installations on the grounds of the airport, which was his personal balloon launch. Beyond Boland's monuments, Thetford boasts Post Mills Church, a historic site aged 206 years, and Thetford Hill State Park, which is lush enough to hide - or build - Vermontasaurus's mate.

Brattleboro

Brattleboro was named for William Brattle, a major-general during the American Revolution. Suffice it to say, the town's history runs deep, and the water is not exactly clean. Beyond colonial warfare, Brattleboro began the Vermont Asylum for the Insane in 1834. The asylum was quite progressive for the time, as it treated its patients as humans rather than animals or demons. Yet it experimented with electroshock therapy.

Now a National Historic Place, the asylum is still in operation but called Brattleboro Retreat and bereft of shocking treatments. A tower and graveyard from its original iteration can be accessed via the parking lot of the Harris Hill Ski Jump. Twelve minutes east of town, in the middle of the New Hampshire woods, is another cryptic ruin: the crumbled castle of Madame Sherri, a Manhattan costume designer who threw lavish parties for her elite friends. A stone staircase is the most striking remnant of this mini Bohemian Grove.

Jay

Jay is a Vermont town so far north it straddles the Canadian border. Naturally, there is a lot of open space up yonder, which is why it became the testing ground of super-secret and super-controversial Space Research Corporation. A 172-foot supergun was just one of the high-altitude weapons found on the grounds, which began as a joint American-Canadian government operation and then went private, running from the 1960s to 1980s and resulting in the imprisonment and assassination of its arms-smuggling operator. The grounds are a treasure trove for thrill seekers. Jay's open space also lends itself to non-controversial recreation. A mountain called Jay Peak hosts Jay Peak Resort for skiiers, while its Jay Peak Trail Running Festival caters to runners on Labor Day Weekend.

Shelburne

Shelburne is seven miles from "big" Burlington but might as well be a world away. Case in point: Shelburne Farms, a 1,400-acre farm on Lake Champlain with everything from cows to sheep to an inn dating back to the 19th century. Just a couple miles south of the farm is Shelburne Museum, which spans 45 acres, comprises 39 buildings, and houses 100,000 pieces of folk art. Take another trip south, this time to the tiny community of New Haven, and search Evergreen Cemetery for the grave of Timothy Clark Smith, who was buried in 1893. There will be no mistaking it, because it has a window because he feared being buried alive.

Already offbeat as a whole, Vermont's small towns are extra offbeat. These communities like Northfield, Bennington, Waterbury, Glover, Proctor, Thetford, Brattleboro, Jay, and Shelburne, have almost as many quirky, creepy, and mind-blowing attractions as they do people. This only scratched the surface of rural Vermont's curiosities. Go and discover more.