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Vermont is a stunning state full of charming culture, lush green hills, and impressive mountain vistas. This lush state is known for having some of the best skiing opportunities around, as well as impressive resorts and boundless opportunities for outdoor adventure. Whether prospective visitors are looking to escape into the wilderness, soak up some history, or take in a unique experience such as hot air balloon riding, Vermont is full of underrated towns to explore. Stay for a weekend, or make a longer vacation of it, to take in everything from maple syrup to quaint historical towns, covered bridges, or stately winter resorts!

Warren Falls

The town of Warren sits in the Mad River Valley, in Washington County, and has a population of just under 2,000. It is wedged between the two ranges of the Green Mountains, which offer not only amazing views but wonderful places to explore and adventure like the infamous Green Mountain National Forest. There are plenty of things to do in this small town, including skiing at the Sugarbush Ski Resort in winter, or kayaking, paddle boarding, and hiking in spring, summer, and fall. The Warren Falls are a beautiful place to explore, as are Warren Riverside Park and Blueberry Lake. On hot summer days, cool down in the many swimming holes such as Lareau Swimming Hole, Great Eddy, or Ward’s Swimming Hole. Hiking enthusiasts ought to visit the Mad River Path, the Warren Path, the Millbrook Trail, and the Long Trail Loop. For tourists looking for something a little more adventurous, try horse riding at the Vermont Icelandic Horse Farm! After a day of exploring make sure to relax and grab a drink at one of Warren's many popular bars and breweries such as Prohibition Pig. 

Weston

Weston is also located near the Green Mountains and is located in the Green Mountain National Forest. It is a picture-perfect small town, full of charm and history. Less than 600 people call this town home giving it that quintessential strong community feel and welcoming environment. The stunning views are one of the most impressive things about the region and draw visitors to Weston year-round. The town is the perfect place to stay for those looking to explore the vast National Forests whether by hiking, mountain biking, fishing, or camping. In town, there is a sense of old-º£½ÇÉçÇø charm. The Weston Playhouse and Village Green are great places for entertainment or live concerts, while the Weston Priory is home to Benedictine monks, making it a unique place to enjoy a calm tranquil escape.

Waitsfield

Like Weston, Waitsfield also has a population under 1,000 however it is estimated that less than 250 people call this town home year-round. This makes it an excellent option for those looking to get off the beaten path and explore a less-crowded town in scenic Vermont. Weston is a four-season destination and its lush Mad River Valley location offers gorgeous natural landscapes in all seasons. Visitors can enjoy hiking, fishing, hunting, and boating in the warmer seasons, as well as catch the Vermont Festival of the Arts in August. This festival is a great way to experience the local arts scene and shop for memorable gifts or souvenirs. Fall in Waitsfield is full of stunning colored foliage, one of the biggest draws for those visiting Vermont. As the leaves change with the seasons, already beautiful scenes are painted with fire reds, deep rusts, bright oranges, and sun-bright yellows making for a masterpiece of natural beauty. Waitsfield in the winter comes with excellent skiing conditions. Mad River Glen Ski Area and Sugarbush Ski Resort are particularly popular for skiers, snowboarders, and anyone looking to enjoy some great runs and fresh powder. Whichever season visitors make their way here, they will be sure to find something special in Waitsfield.

Stowe

Stowe is located not far from Waitsfield and is another tiny town with a lot of heart. It has a population of around 600 and is also a popular year-round destination for travelers. Stowe is generally considered a mountain resort town as it sits at the base of Vermont’s highest peak. Its outdoor recreation options are plentiful, from skiing and snowboarding at the much-loved Stowe Mountain Resort to exploring cross-country ski trails at Stowe Nordic. In the fall, the autumn leaves are beautiful, and hikes around Sunrise Mountains and the Green Mountain range offer impressive views of the yearly change. Hiking, mountain biking, horse riding, and other recreational activities are common in fall, spring, and summer, but Stowe also has a variety of more unusual attractions. Enjoy hot air balloon rides at Stoweflake Mountain Resort, for a once-in-a-lifetime experience. Floating effortlessly above Stowe will not only give you an amazing bird's eye view, but a tranquil escape into the clouds. ArborTrek Canopy Adventures is another excellent option for those looking for a more fast-paced experience. Enjoy ziplining through the canopies or gliding through the forests. Dog sledding at Eden Ethical Dog Sledding is another great option for those visiting in winter. This ethical dog sled experience allows visitors to adventure through the winter wonderland pulled by a team of hard-working pups. For arts and culture, check out the Bryan Fine Art Gallery, outdoor performing arts center, and Stowe Historical Society Museum to learn more about the history of this amazing town. 

Brandon

The town of Brandon is an underrated town that sits between Middlebury and Rutland. Brandon is another excellent place to stay for those visiting the Green Mountain National Forest. In particular, the Moosalamoo National Recreation Area is right on Brandon’s doorstep. It is an excellent option for those looking for outdoor adventure - no matter the season. Enjoy mountain biking, hiking, bird watching, climbing, and so much more in this wilderness paradise. Those looking to enjoy the small-town charms of Brandon can experience over 246 historic buildings, including the unique Greek-style architecture of the Brandon Town Hall. Brandon is also home to Park Street, which has been called ‘the most beautiful street in Vermont’ due in part to its gorgeous houses and landscaping. Visitors can enjoy staying in a classic Bed and Breakfast, or one of the local inns to soak up the full town experience. Delicious food options and cafes, art galleries, and studios are all within walking distance of most accommodations. 

Chester

Chester is another New England town with a quaint vibe. Like Stowe, it also has proximity to skiing opportunities, including Okemo Mountain Resort, Stratton Mountain Resort, and Killington ski areas which offer some of the best skiing opportunities in the country. Enjoy excellent comfort food at Country Girl Diner, or a more upscale meal at Fullerton Inn or Inn Victoria, which double as excellent places to stay. History buffs will love the Stone Village Historic District and the main street of town which boasts various buildings on the National Register of Historic Places. Chester also has a vibrant antique scene, including the Stone House Antique Center. For outdoor lovers, you can enjoy the proximity of hiking trails, mountain biking opportunities, and beautiful outdoor spaces. Magic Mountain, Mount Snow, Okemo Mountain Resort, Killington, Stratton, and Bromley are all close by and are a great way to explore the town’s surrounding areas.

South Hero

South Hero, Vermont is located on South Hero Island in Lake Champlain. The town traces its roots to 1783 when the first settlers arrived by boat. This lush and fertile land makes it the perfect place for farming, and apple orchards and dairy farms are still common in the area. Visitors can enjoy local farms and shops including apple orchards like Hackett’s Orchard, and Snow Farm Vineyard, and local farms selling fresh meat and eggs like Pigasus Meats and Health Hero Farm. Other activities in the area include exploring the expansive shoreline of Grand Isle State Park or hiking some of the many trails in the area. The Island Line Trail is arguably the most popular bike trail and connects South Hero to the larger city of Burlington. Other trails include Landon Community Trail, Roy Marsh Trail, and Round Pond Natural Area. Fox Hill is also a great option and offers gorgeous views of Lake Champlain and the mountains beyond.

Shelburne

Shelburne is another small town near Lake Champlain. Like South Hero, it is also conveniently located only 7 miles from the larger city of Burlington, making it a great escape for those looking for a quiet getaway or somewhere to enjoy the beautiful lakeside views, hiking, or camping. The town itself was established in 1763 and was formed mainly on farming businesses. One of the most popular tourist attractions is the Shelburne Farms, which is now a historic working farm campus that helps educate and promote sustainable farming options. For more history, travelers can visit the Shelburne Museum and the Vermont Teddy Bear Factory. Shelburne also has a strong community feel, and various concerts, events, and festivals take place within the town center for all to enjoy. 

Putney

The town of Putney is part of Windham County, Vermont. It holds a lot of charm and character and is both a great place for a weekend getaway, and the perfect quiet escape as a day trip from New Hampshire or New York. The town’s eastern border is the Connecticut River, which runs along the Vermont and New Hampshire border. The downtown area is largely made up of the Putney Village Historic District, which is listed on the National Register of Historic Places. It includes notable buildings such as the Theophilus Crawford House which was built in 1808, the East Putney Brook Stone Arch Bridge from 1902, the Sacketts Brook Stone Arch Bridge, and the Sabin-Wheat Farm which was first established in 1790.

Island Pond

Island Pond is part of the town of Brighton and is one of Vermont’s best-hidden gems. The town sits on gorgeous Island Pond Lake, with the Bluff Mountains overlooking it all. It is a great place for outdoor lovers and adventurers as it includes everything from hunting and fishing to swimming, hiking, canoeing, mountain biking, horseback riding, and skiing. Island Pond is also known for having extensive snowmobile trails and is the snowmobile capital of Vermont. The town also holds a lot of history. It was one of the earliest international railroad junctions and has a distinct historical district downtown which highlights the town’s early connections to Maine and beyond to Canada.

Dorset

Dorset traces its beginnings back to 1761 and has strong historic roots and New England charm. Its location in southern Vermont is also known for its impressive landscapes, including mountains and valleys. Top attractions include the Merck Forest and Farmland Center where visitors can enjoy a hike through 3,200 acres of trails featuring lovely views, or explore the farm center and its many animals. Other recreational areas include the stunning Emerald Lake State Park where visitors can enjoy fishing, kayaking, canoeing, or taking on one of the many hiking trails. The Dorset Quarry has beautiful marble cliffs and is a popular place for a swim in the summer months. In town, don’t miss the Historic Dorset Village including the Dorset Inn and the Dorset Union Store. The community is big here, and the farmer’s market is a great way to mingle with locals and get a real feel for the town. You can also attend the Dorset Theatre Festival in the summer. It is usually in the latter half of June.

Whether you’re an avid skier, love hiking, or simply want to explore somewhere new, Vermont is a great option full of underrated towns. Rather than hitting Montpelier, Burlington, Barre City, or Essex Junction, these small towns offer a window into the heart of Vermont. Get to know locals, dine at a cafe, take in a farmer’s market or festival, or simply soak up some history in a local museum. Visiting small towns in Vermont offers a unique chance to get off the beaten path and enjoy a slower-paced lifestyle, full of beautiful landscapes, friendly people, vibrant history, and memories that will last a lifetime.