6 Playfully Peculiar Towns In Vermont

Did you know that Vermont has towns that are a little off? With its quiet back roads and small, collective communities, Vermont is hidden in the valleys between the Green Mountains and deep woods. Vermont was a republic before becoming part of the United States in 1791. You won’t find orchestrated photo ops or theme parks here. You will discover strange roadside stops, weird attractions, and places that weren’t designed with outsiders in mind. These towns have character but also markets, concerts, trails, and unexplainable carvings. You probably weren’t meant to find them, but you did. Pack a lunch, head to the back roads, and try the stranger side of Vermont.

Waterbury

Ice cream born in Waterbury dies in Waterbury. Start by visiting the Ben & Jerry’s Flavor Graveyard, which features whimsical epitaphs for discontinued flavors like ‘Economic Crunch’ and ‘Wavy Gravy’. It’s a short walk behind the factory and an odd but authentic tribute to ice cream’s past.

After a good laugh, take the Ben & Jerry’s Factory Tour, which walks you through the production line and ends with a scoop of ice cream. Then head five miles west to Little River State Park, where quiet lakeside trails and shaded picnic areas reveal remnants of a 19th-century village. For dinner, enjoy pulled pork and craft beer at Prohibition Pig. If you’re in town in early September, don’t miss the Waterbury Arts Fest, an arts, music, and food street fair.

St. Johnsbury

Faith, fur, and whiskey set this town apart. Start at Dog Chapel, built by artist Stephen Huneck after a near-death experience. He wanted to honor the bond between humans and dogs. The chapel welcomes all faiths and lets dogs roam freely. Visitors cover the walls and ceiling with photographs, notes, and collars to remember their pets. It’s quiet, odd, and unforgettable.

Then, bike or walk the Lamoille Valley Rail Trail, which winds through farmland and forest just north of town. Afterward, head to the St. Johnsbury Distillery Tasting Room & Speakeasy for small-batch spirits and experimental cocktails. In summer, catch a live show at the Levitt AMP St. Johnsbury Music Series, held downtown on Sunday nights.

Dorset

This town’s story is carved straight into the marble. Start at the Freedlyville Quarry, a marble tunnel from the 1800s now loved by ice skaters when the inside freezes in winter. The cold lingers, making it a surreal stop any time of year.

Take a short drive to the Dorset Marble Quarry, the oldest in the U.S., now a favorite spot for swimming and cliff jumping. Visit H.N. Williams General Store, a family-run shop since 1840, where you can find tools, snacks, and local goods. If you’re visiting in August, catch SATELLITES: A New Interstellar Love Story during the Dorset Theatre Festival, from August 6 to 16.

Burlington

The tallest filing cabinet on Earth lives here. In 2002, artist Bren Alvarez created File Under So. Co., Waiting for…, a 38-drawer monument to a highway project that never happened. Locals have turned it into a public diary, covering it with stickers and scribbles.

Ride at the Burlington Bike Park, an urban dirt track with jumps and pump sections for all skill levels. Cool off at Foam Brewers, a waterfront hangout with hazy IPAs and small bites. End your day with a sunset cruise on the Spirit of Ethan Allen, a narrated tour circling Lake Champlain.

Bellows Falls

This town begins with a mystery no one has solved. The Bellows Falls Indian Petroglyphs are carved into the west side of the Connecticut River. These abstract faces have puzzled locals and historians for years. No one knows who made them or why, but they remain chiseled, weathered, and strange.

After the river, visit Morning Star Perennials & Nursery, a small but vibrant garden shop. Browse Windham Antique Center next, with vintage books, records, and furniture in a classic brick space. Finish your trip at Stage 33 Live, a cozy music venue with a full schedule running through October.

Hancock

The geological star here is Texas Falls, found inside the Texas Falls Recreation Area. These stepped waterfalls and glacial potholes formed over thousands of years, where swirling water sculpted deep, smooth holes in the bedrock. You can view them from the footbridge or hike the short interpretive trail to see more.

Afterward, go into town for lunch. Hubbard’s Country Store serves sandwiches and drinks, or relax with a meal at Hancock Village Café, known for its small-town feel. Stick around for the Hancock Green Summer Concerts, held on the village green through summer and popular with locals.

Each of these six towns offers something strange and worth seeing. Maybe it’s a marble pit turned swimming hole, a chapel for dogs, or ancient petroglyphs carved in stone. These towns aren’t frozen in time, but haven’t changed much. They host music, show art, and carve trails without fanfare. Forget franchises and tourist centers. Think speakeasies in barns, live music in garages, and waterfalls carved by glacial melt. You’ll find people doing things their way, like they always have. Open your itinerary and take the slow road into Vermont’s offbeat corners if you want something real.