6 Quirkiest Vermont Towns To Visit In 2025

Vermont is a classic New England state full of incredible natural scenery, including some of the tallest mountains on the East Coast. What it lacks is big cities and large metro areas, with Burlington being its biggest by far, with nearly 45,000 residents. However, this only adds to the charm of Vermont, as many come here to escape into the wild.

While roughing it out in the woods can be fun, it can only last so long for most people. Eventually, you will likely have to resupply, gas up, and grab a comfy bed for the night. With that in mind, why not make it enjoyable? Here are the six quirkiest communities in the Green Mountain State that you should consider visiting for your next outing.

Glover

Tucked into a region called Northeast Kingdom, which comprises the far northeastern corner of Vermont, Glover is a remote community that has carved out a name for itself with offbeat art installations, a unique history, and rural charm.

This town is perhaps best known as the home of the Bread and Puppet Theater, a performing puppet troupe founded in the 1960s. It is headquartered in a space filled with a huge collection of masks and puppets, ranging from politically themed to comical or downright eerie. A few minutes south of town, the Museum of Everyday Life offers a rotating showcase of, well, everyday, ordinary objects. Here, you'll see many fascinating items, like nail clippers, dust, and toothbrushes, each treated with archival reverence and philosophical commentary. Both museums operate on donation-based entry and are housed in repurposed barns.

While the town lacks a formal downtown, a cozy spot like the Red Sky Trading is an all-purpose roadside stand that sells anything from antiques to homemade pickles. A small collection of grocery markets and eateries can also be found nearby, making it a decent place to stop on a road trip.

Waterbury

Two major attractions anchor Waterbury: the Ben & Jerry’s Factory and Vermont Artisan Coffee & Tea Co. The Ben & Jerry’s facility offers tours of its production line, a scoop shop, and the well-known Flavor Graveyard, where discontinued ice cream flavors are commemorated dearly. A 10-minute drive from there will take you to the other local culinary hotspot, Vermont Artisan, which operates a roasting and tasting facility open to the public, with on-site sales of small-batch coffee and equipment.

In town, historic brick buildings house more restaurants, bookstores, and the Prohibition Pig, a smokehouse and brewery. Enjoy the outdoors around Waterbury, too, at the Waterbury Reservoir, part of the nearby state park. This locale allows for boating, swimming, and hiking along the shoreline, with boat rentals available during the warmer months. Furthermore, the Green Mountain Club maintains a visitor center just outside town with maps and trail access for the Long Trail and Mount Hunger.

Waterbury also serves as a staging point for trips to Worcester Range. The Amtrak station and proximity to I-89 make it one of the more accessible small towns in this mountainous part of the state. It doesn't hurt that it's also about a 15-minute journey by car from Vermont's capital, Montpelier (the nation's least populated capital city).

Greensboro

Greensboro is home to Hill Farmstead Brewery, a true destination for beer enthusiasts regularly ranked among the best in the world. The brewery operates a tasting room and retail shop on a rural road just outside town, a perfect place to stop after a visit to another local draw, Caspian Lake. This pristine body of water is open to the public and is a hotspot for swimming, boating, and fishing, with a designated beach not far from the town center. The shores of Caspian Lake also feature the Bayley-Hazen Monument, a historic landmark dedicated to two of the area's pioneers killed in 1781 while guarding the adjacent road.

For more outdoor fun, a quick drive north leads to Barr Hill Natural Area, a conserved hilltop with hiking trails and open views of the Northeast Kingdom. Nearby, the Hazendale Farm Stand sells organic produce, meat, and prepared foods grown and made on-site.

Another business worth checking out is the Willey’s Store. This unassuming shop functions as a general store, hardware supplier, and clothing outlet, and has notably been operating since 1900 by only one family.

This community is also a bit of a creative hub, as the robust Highland Center for the Arts runs a year-round schedule of performances, gallery shows, and film screenings in a contemporary venue nestled in the surrounding farmland.

Rochester

Rochester sits along Route 100 and is known for various fun, community-oriented attractions such as pop-up markets, art fests, and outdoor concerts. It is also surrounded by beautiful natural surroundings, resting at the foot of the eastern slopes of the Green Mountains.

However, in terms of its more unique draws, BigTown Gallery displays contemporary visual art and regularly hosts literary events featuring nationally recognized writers. Nearby roadside stops include Maple Soul, a restaurant that blends typical Vermont farm fare with a rotating seasonal menu in a beautiful old house downtown.

Meanwhile, outdoor enthusiasts can access mountain biking trails in the Green Mountain National Forest directly from town, and in winter, snowshoeing trails are maintained right near the village center. Mt Cushman State Park can also be accessed just east of town for a quieter outing into the nearby woodlands.

Tunbridge

Tunbridge is a local favorite in New England. It is renowned for hosting the Tunbridge World’s Fair, a century-old agricultural fair held every September. The event includes livestock showcases, antique machinery, pulling contests, and a midway, drawing thousands over its usual four-day run.

Outside of fair season, the fairgrounds are quiet but still accessible and worth checking out. Several historic barns and even one of Vermont's famous covered bridges are adjacent to the site. The Mill Covered Bridge and Cilley Covered Bridge are located on small local roads and are still in use.

Have a sweet tooth? Howell’s Maple Farm offers tours of its various maple production sites and sells products in season (late winter to spring). Furthermore, scenic drives along Route 110 pass old farms, more sugarhouses, and stone walls typical of the White River Valley.

Chester

Chester’s most recognizable feature is the Stone Village, a stretch of 19th-century houses built from locally sourced granite. The structures are practically all private homes, but are viewable from the sidewalk. A short walk connects this area to the Chester Depot district, which contains other delights like antique shops, some restaurants, accommodations, and other amenities.

Multiple inns and small markets are located within town limits, but commercial development remains limited to independent businesses. Parking is available along Main Street and at the depot. Be sure to check out local DaVallia Art and Interiors, which showcases regional artists and has most works available to purchase.

Regarding historic landmarks, the Whiting Library and Yosemite Engine House are part of a cluster of historic civic buildings near the town green. Moreover, the Green Mountain Railroad occasionally operates foliage and themed train rides from the depot, especially in fall.

If you get the chance, you should experience the natural environment here even closer by walking down the Pinnacle Trail just outside town. This charming route provides a brief, marked path to a ridgeline with partial views over Windsor County.

Enjoy all of Vermont's Quirky Charms

Whether in search of a new, quiet park to explore, a historic downtown core you've never heard of before, or an obscure museum, these spots are sure to deliver a taste of Vermont's sometimes offbeat vibes. So, the next time you travel through this wonderful landlocked state, see a side that not everyone can experience.