Evening landscape and rustic buildings in the town of Stowe, Vermont.

7 Most Unconventional Towns In Vermont

At just 9,616 square miles, Vermont is one of the smallest U.S. states. Compared with nearby New York state, over five Vermonts could fit into New York. Yet, Vermont packs a lot of towns inside its borders. These towns provide some excellent opportunities for winter sports, from downhill and cross-country skiing to snowboarding, ice skating, and sledding. Vermont is a four-season state, with spring, summer, and fall, providing excellent trails to be hiked or biked, lakes to paddle, and some of the best foliage colors in the United States. Lesser known are the towns that have hidden surprises to share with visitors in the know. Towns like Shelburne, for example, whose museum has more individual structures than all of the Smithsonian. Or Ripton, where visitors can revel in Robert Frost's poetry outdoors in the environment he loved. These towns give you the chance to see Vermont from all-new perspectives.

Brattleboro

Rustic buildings in Brattleboro, Vermont.
Rustic buildings in the town of Brattleboro, Vermont. Editorial credit: jenlo8 / Shutterstock.com

This southern Vermont town might be the only place in the world where you can experience fine art, a literary festival, and a cow parade in its award-winning downtown. From May through December, Gallery Walk takes place every first Friday of the month from 5 pm to 9 pm to view the work of local artists while enjoying music, food trucks, and more. During the first weekend in June, Strolling of the Heifers features local cows wearing floral garlands led by future farmers. In fact, Brattleboro's Holstein Association registers every black-and-white Holstein-Friesian cow in the country. Then, in the fall, the Literary Festival features two to four days of famous, local, and up-and-coming authors participating in readings, presentations, poetry slams, Literary Death Match, and other novel events.

If you miss out on the events, there is still lots to do in this unique destination. Downtown shops like Beadniks and Hippie Twigs pay homage to the town's hippie vibe of the '60s and '70s. Brattleboro and surrounding regions have always attracted writers, including Pearl Buck, Rudyard Kipling, and Sinclair Lewis. Today, visitors can pick up a map of the self-guided Brattleboro Words Trail that narrates stories as they walk by.

Shelburne

Shelburne, Vermont.
Historic Ticonderoga Steamboat off of Shelburne Road in Shelburne, Vermont. Editorial credit: John Arehart / Shutterstock.com.

A town on the edge of Lake Champlain, Shelburne has many beautiful places to enjoy, from beaches to mountains. What makes the town so unusual, however, is its museum. The Shelburne Museum has 39 buildings on 45 acres. The buildings are also unusual, not the typical four-walls-and-a-roof square structures visitors are accustomed to envision. Ranging from a one-room schoolhouse and a lighthouse to a covered bridge and a steamboat, each was selected by the museum's founder, Electra Havemeyer Webb, and moved to the museum's land. She began the museum thinking she would showcase her parents' collection of carriages, and it does. The museum also holds one of the most diverse collections ever displayed, from fine and folk art to toys, duck decoys, and circus memorabilia. On the other hand, outdoor activities abound at the Lake Champlain Yacht Club and Shelburne Bay Park. Visitors can hike, boat, and swim in these lush areas for some fun under the dun. Afterward, stay at the quaint Heart of the Village Inn bed and breakfast and experience local hospitality.

Stowe

Ski lodge in Stowe, Vermont.
Ski lodge in Stowe, Vermont.

Most people know of Stowe for its snow and the ski resorts that thrive because of it. While it is certainly worth venturing there for this reason, Stowe has another lesser-known attraction: the Trapp Family Lodge. Situated in Vermont's Green Mountains, it almost feels like The Sound of Music movie's setting in the Austrian Alps. The lodge itself has 90+ rooms, plus chalets and villas on the 2,600-acre property. Rooms in the lodge feature one king or two queen beds, and some have sleeper sofas. Many have balconies or patios with mountain or orchard views. Moreover, the lodge features four restaurants, various venues, and events such as the Poker Ski Event in January.

Outside, Stowe's hills are alive with four seasons of activities. In winter, the Trapp Family Lodge and Stowe Mountain Resort offer skiing, snowboarding, dog sledding, dog carting, snowmobiling, and snowshoeing. The other seasons offer hiking, biking, climbing, tennis, golf, and more, opening up opportunities to explore landmarks such as Sterling Gorge Falls.

Ripton

Robert Frost Cabin in Ripton, Vermont.
People visiting the Robert Frost Cabin in Ripton, Vermont. By Aiken1986 - Own work, CC BY 3.0, Wikimedia Commons.

One thing about Vermont's small towns is that they are close together, so activities in one often spill into another. While the Robert Frost Interpretive Trail is often mentioned as being "near Middlebury," its trailhead is actually in Ripton on Rt. 125. Parking is on one side of the road, and the trailhead is accessed across the road. Also called the Robert Frost Wayside Trail, it is an easily hiked 1.3-mile loop. The first .5 mile is wheelchair accessible by a walkway that juts out into the Middlebury River. Several of Frost's poems are printed on markers along the trail for hikers to stop, read the poem, and reflect on it while surrounded by nature.

Look to Middlebury when hunger calls, like fine dining at Jessica's at Swift House Inn or more casual yet raved-about pizza at Two Brothers Tavern. Those here for a few days can stay in Ripton at the Stable Inn or Robert Frost Mountain Cabins.

Westmore

Lake Willoughby in Westmore, Vermont.
View of Lake Willoughby along the town of Westmore in Vermont. By Mwparenteau - With my camera at a weddingPreviously published: Simultaneously published on Flickr and Facebook, CC BY-SA 3.0, Wikimedia Commons.

In Westmore, scenery abounds, with a unique environment rarely seen elsewhere. Mount Pisgah and Mount Hor form the backdrop for Lake Willoughby, which was carved by glaciers over many thousands of years. The five-mile-long, finger-shaped lake gives it the appearance of a Norwegian fjord rather than the typical roundish lakes in the U.S. Sandy beaches are perfect for enjoying the view, whether from a kayak, paddleboard, or lounge chair. The lake is 300 ft. at its deepest point, making it an ideal spot for diving as well.

Ardent hikers will want to hit the trail leading to the summit of Mt. Pisgah, a challenging hike that takes an average of three hours. Actual hikers describe the trail as steep, rocky, and muddy in parts but well marked and well maintained. Dogs are welcome and can be off-leash in some places. This is a popular trail, so expect to see other hikers and bird watchers. After the hike, book a room at the WilloughVale Inn & Cottages for a comfortable stay along the water.

Manchester

Exterior architecture and beautifully landscaped gardens of Hildene, The Lincoln Family Home in Manchester, Vermont
The gardens of Hildene, The Lincoln Family Home in Manchester, Vermont. Editorial credit: Theresa Lauria / Shutterstock.com

Fly-fishing enthusiasts or rookies can learn the basics or perfect their craft at the Orvis Manchester Fly-Fishing School in the town where Charles Orvis started it all with a modest tackle shop in 1856. The Orvis family owned the company and grew it to prominence over the next 100+ years. The Perkins family bought Orvis in 1965; today, Simon Perkins is Orvis' President. Although free lessons are offered at Orvis stores, the school offers one-day and two-day classes.

Manchester was a popular summer resort town in the 1850s, and many presidents visited it, including Abraham Lincoln and his wife, Mary Todd Lincoln. Their son Robert Lincoln bought property in the town and built a summer home, Hildene. Public tours of the mansion and opulent gardens are offered, including a goat dairy. While these sites make Manchester an unconventional getaway, it still has the charms of a tourist hub, including great shopping. Manchester Designer Outlets is an ideal place to start, with stores like Brooks Brothers, Polo Ralph Lauren, and Talbots at outlet pricing.

Waterbury

Ben & Jerry's Ice Cream Factory in Waterbury.
Ben & Jerry's ice cream factory in Waterbury, Vermont. Image credit Wangkun Jia via Shutterstock.

If you thought Waterbury was in Connecticut, you are correct. Many early settlers of Waterbury, Vermont, hailed from its namesake, and the two towns have a history of mutual support during tough times. Today, Waterbury, Vermont, offers attractions for all seasons, but its most famous draw is the Ben & Jerry's Factory Tour. Opened in 1978 in a repurposed gas station, the iconic ice cream company now invites visitors to learn about its production process, taste-test unique flavors, and discover its sustainable practices, including the Caring Dairy program. Tours last 30 minutes and are a hit with families, but tickets sell out quickly, so booking in advance is essential.

Beyond Ben & Jerry's, Waterbury boasts a vibrant downtown filled with charming shops, cafes, and breweries. Visit Prohibition Pig for delicious barbecue and craft beer, or explore the Waterbury Reservoir for hiking, kayaking, and picnicking amidst stunning natural beauty. The town is also home to Cold Hollow Cider Mill, where you can savor fresh cider, apple donuts, and Vermont-made products.

Hidden in Plain Sight

Who knew Vermont had so many surprises to uncover? A town that celebrates cows, one that put fly-fishing on the map, and another with a penchant for ice cream and a better world. When planning your next getaway, you have an added advantage. There are more places to explore, learn, hone your skills, and enjoy the outdoors and the great indoors. So go to Vermont and play in the snow. Then come back and bask in the rest of the seasons, stories, and showcases that are all in Vermont.

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