8 of the Most Charming Small Towns to Visit in Vermont
In the New England region of Northeast America lies a landlocked state, also dubbed the Green Mountain State, popular for the forests that corner it, the mountainous terrain that includes the famous Green Mountains, and its much-respected maple syrup.
Known for its liberal politics, Vermont also happens to be the second least populous state in the United States of America. This state is a regular tourist spot as thousands of people from different parts of the world throng in, especially during fall, to witness its fall foliage.
The natural landscape of Vermont is an immersive and exciting experience for tourists. This state’s small size and population make it the ideal vacation destination, as you can enjoy the charm and idyllic nature of the town. If you want to visit Vermont for leisure, then you should check out these eight charming towns that will make your holiday worthwhile.
Waitsfield
Situated along the Mad River Valley, which provides water power for the town's mills, Waitsfield was created in February 1782 by a small Vermont charter and later named after General Benjamin Wait. Waitsfield has since evolved from an agrarian town to being a desired tourist destination popularly known for its ski resorts.
For an unforgettable experience, you have to begin at Mad River Glen, which has one of the most unique and challenging ski experiences in the East. The town is really invested in skiing, and you would meet most of the locals there.
You could also experience the arts and culture scene in Waitsfield at the Big Picture Theater and Cafe and the Mad River Glass Gallery. For the best hiking and biking experience, you should pay a visit to the Mad River Path, as it has a network of trails that you would not find anywhere in the country.
Bennington
Founded in 1749 and located in southwest Vermont is Bennington, one of the earliest settlements in Vermont, which is famous for its role in the Revolutionary War, particularly the 1777 Battle of Bennington. Following the war, the Battle of Bennington monument was erected to commemorate the victory.
The monument is the tallest structure in Vermont, and visitors can get a view of the obelisk from a distance.
The Bennington Museum has an impressive collection of artifacts and art, such as the Grandma Moses collection, which is an ideal spot for history enthusiasts. You can also visit the Bennington Center for Arts to see more paintings and collections.
Willow Park, downtown Bennington, has a large playground for kids, an 18-hole disc golf course, and athletic fields, which you can visit during the day. You might also like to visit Bennington College and Burt Henry Covered Bridge to learn about the great history of the town.
Manchester
Just thirty minutes off Bennington is Manchester, the second shire county in Bennington, Vermont. This town is the favorite tourist destination for folks coming from New York and Connecticut looking for a place to stay away from the hustle and bustle of the city.
Amongst the many landmarks and attractions in Manchester is the Hildene Mansion. The Georgian Revival-style mansion is the summer home of Robert Todd Lincoln, the only child of President Abraham Lincoln.
Mount Equinox is one of the popular sights in the town and is good for hiking. In Manchester, the Riverwalk offers a scenic exploration along the West Branch of the Battenkill, distinct from the nearby Mount Equinox, where the Southern Vermont Arts Center (SVAC) provides cultural enrichment with art exhibitions and collections from regional artists such as Robert Strong Woodward and Ogden Pleissner.
Woodstock
Chartered in 1761, Woodstock is the shire town of Windsor County. The rapid development of Woodstock was due to the abundant water power of the Ottauquechee River, which also facilitated the development of various mills along the river path.
The town's unwavering commitment to preserving and appreciating the natural environment has earned it the status of the prettiest small town in America, as its scenic mountain and forest backdrop is constantly maintained. Sites of interest in Woodstock include the Marsh-Billings-Rockefeller National Park, which provides amazing insights into America's history.
The Lincoln-covered bridge built in 1877 will grab your attention if you are a history buff, as well as the Billings Farm and Museum, which provides visitors an opportunity to learn about sustainable farm practices and 19th-century farm activities. Woodstock Historical Society & Dana House Museum houses paintings, textiles, and clothing that you might love.
Brattleboro
Sited in southeast Vermont, Brattleboro is a charming town with a rich history and a vibrant arts scene. Popularly known as the Gateway to Vermont, Brattleboro offers visitors a perfect blend of cultural attractions and outdoor adventures.
The Brattleboro Museum & Art Center is a popular attraction in town as it showcases contemporary art exhibitions and gives insight into regional history. For outdoor enthusiasts, the nearby Connecticut River offers opportunities for kayaking, fishing, and scenic boat tours. The Gibson Aiken Center and Living Memorial Park are great spots to host the family.
Brattleboro hosts various festivals and events to celebrate the town's culture and heritage, and you do not want to miss them. The Strolling of the Heifers Parade is held annually in June. This unique parade features colorful floats, live music, and herds of decorated cows, referencing Vermont's agricultural heritage.
St. Johnsbury
Located in Vermont's idyllic Northeast Kingdom, St. Johnsbury is a charming town renowned in history and surrounded by natural beauty. In the mid-19th century, it was a minor manufacturing center for scales and Maple syrup.
The town is deeply connected to its roots and places such as St. Johnsbury Athenaeum, a historic library and art gallery where you can see a collection of fine art and rare books, and the Fairbanks Museum and Planetarium, where visitors can explore exhibits on natural history, science is a must-visit location.
Outdoor enthusiasts will appreciate the nearby trails of the Kingdom Trails network for hiking, biking, and cross-country skiing. Cherry House Bed and Breakfast and Fairbanks Inn are spots in town where you can enjoy the food and hospitality of the town.
St. Johnsbury hosts the Colors of the Kingdom Autumn in September, during which you can enjoy live music, craft vendors, and seasonal activities.
Windsor
Nestled in the Green Mountains is a charming town, also known as the birthplace of Vermont. This town is called Windsor, and its history dates back to the colonial era. Interestingly, Windsor is home to the Old Constitution House, which housed the creation of Vermont's first constitution, which was adopted in 1777.
Do not miss an opportunity to visit the American Precision Museum for a glimpse into the innovation and manufacturing history of America. The Ascutney Trails are perfect for hiking and mountain biking and getting acquainted with stunning views of the countryside.
Windsor also hosts several festivals, such as the Vermont History Expo in June, where visitors can immerse themselves in Vermont's rich cultural heritage. In September, the town comes alive with the annual Vermont Golden Honey Festival, celebrating the state's beekeeping industry.
Newport
Newport is said to be the most charming town in all of Vermont. By experiencing the stunning views of the mountainside, you would tell a tale of the most beautiful place you have seen.
The all-year-round recreational nature of this town makes it a popular destination for both outdoor and nature enthusiasts. For the best local food and accommodation, try the Newport Motel, Derby Four Seasons, or Tavern on the Hill. For outdoor adventure, the incredible Mount Pisgah State Park has miles of hiking trails overlooked by the breathtaking sights of Lake Memphremagog and the surrounding countryside. Be sure to experience the annual Winter Festival in February and the Newport Jazz Festival in the summer, where you can enjoy excellent jazz music from world-renowned musicians. Do not miss a visit to the MAC Center for the Arts, where the works of local artists and artisans are displayed.
Discover Vermont's Quiet Charm
If you enjoy beautiful landscapes and small charming towns, Vermont is your ideal destination. With a rich historical connection, tranquility, and beautifully colored horizons, Vermont offers a breathtaking yet simple getaway from whatever may stress you. These towns are the finer things of life on a platter of gold. You should take up this offer and live life to the fullest and best, even if it is for just a while.
