The Best Small Towns in Vermont to Chill Out In 2024

We can be thankful that our founding fathers decided to be more creative and changed their minds from initially calling this picturesque state New Connecticut. With some of the country’s most magnificent landscapes, Vermont more than deserves an identity all its own. While you think of skiing, maple syrup, and red clapboard barns, the Green Mountain State offers so much more. Serenity settles in, and your blood pressure instantly lowers as you cross the state line. So much so state troopers set up checkpoints. Ok, not really, but no one would ever deny Vermont’s effortless ability to blissfully hypnotize. Find out why it is home to some of the best places to chill in 2024.

Norwich

Established in 1761, this tiny hamlet is one of the most affluent areas in Vermont.

The Montshire Museum prides itself on its ability to teach while allowing visitors to immerse themselves in the exhibits. Stroll along the Planet Walk, a three-mile route that recreates the distances of the planets in our solar system.

Take a cooking class at King Arthur Baking Company, founded in 1790; this mainstay has worldwide recognition for any novice or master baker. Learn how to make your sourdough base or tour the original buildings. The Norwich Farmers Market is one of the oldest continuously operating in New England. It supports the local agricultural industry by visiting stalls that offer baked bread, churned butter, and fresh produce.

Hazen Trail provides the perfect backdrop for a relaxing hike. Breathtaking views abound all year round. Chill out as you become one with Mother Nature and marvel at Hanover Esker, which was formed over the centuries by glacier melt. Book a weekend at the Norwich Inn for an extended stay. Built in 1797, this colonial residence offers New England heritage at its finest.

Stowe

When most people hear of Stowe, they, of course, think snow. Known as the “Skiing Capital of the East,” Stowe has over 120 ski trails spread across 25 resorts, offering options for the novice to the black-run expert. Sandwiched between Mount Mansfield and Spruce Peak, winter sports lovers can try a bit of everything. While, of course, its resorts are unmatched, there is so much more to this charming town all year long. It is the perfect backdrop for any type of chill you want.

During the warmer months, these ski resorts become some of the best hiking and fishing on the East Coast. The Green Mountain Inn, established in 1833, provides families with a full roster of activities for the entire family. The Spa at Stoweflake uses natural minerals from nearby springs to offer over thirty treatments to unwind and rejuvenate.

Fishing is available from the spring through the fall. Cast your reel with experts at Catamount Fishing Adventures, who will help you find the best trout in Stowe.

Middlebury

Chartered in 1761 by New Hampshire Governor Benning Wentworth, who was responsible for founding numerous cities in the region, Middlebury is the county seat of Addison County. Parts of the town were damaged during the Revolutionary War, and its rebuilding in 1783 is the basis of today’s modern-day hamlet.

Over half the town is professionally or personally connected to Middlebury College. Home to The Middlebury College Museum of Art, the campus is the ideal place to chill. Peruse the endless shelves of the two libraries and find a quiet corner to relax.

Lake Dunmore spans approximately 985 acres. At the visitor center, rent a rowboat and enjoy 360-degree views of neighboring towns Salisbury and Leceister.

Tour the vineyards at Lincoln Peak. Founded in 2001, it has quickly become a budding sommelier’s favorite stop in Vermont. With award-winning Chardonnay, this family-run business offers tastings and informative seminars on the region’s history.

Woodstock

Founded in 1761, Woodstock was home to some of the nation’s first entrepreneurs and business people. Named one of the prettiest American towns to visit in the winter, it is among Vermont’s top tourist destinations during the holidays. Wassail Weekend in December recreates an immersive Dickens experience. Period costumed entertainers adorned in holly and ivy line the streets. Best of all, Woodstock is the perfect place to chill all year round.

Home to three covered bridges, it’s the ideal backdrop for your Instagram. Middle Covered Bridge is in the center of town. Stroll the nearby shops that line The Green. Find local artisans and farm-to-table cuisine.

Billings Farm and Museum is a short drive away. This working dairy farm, on over 200 acres, provides a great afternoon of fun. Pick fruit, ride the tractors, and tour the historic barns.

Chester

Famed for its Stone Village Historic District, Chester was incorporated in 1754 by Governor Benning Wentworth. With multiple listings on the National Historic Registry, it has become a much-wanted stop for colonial enthusiasts.

The historic village came about with a bit of divine intervention, literally. The Congregationalists and the Baptists had differing views on where to build their places of worship, so they finally settled their respective chapels on the North and South sides of the district. The historic downtown is between the two.

Stone Village is home to unique shops and pubs, all along 18th-century mason masterpieces. The buildings alone are worth visiting, but stop at Stone Village Farmers Market for fresh farm offerings.

For those who like a bit of exercise, explore the Lost Mine Trail. Due to some tricky elevation, it is not ideal for small children, but adventurers are rewarded with magnificent views of the lakeside. Locals recommend going in the fall for unobstructed panoramic fall foliage.

Dorset

This quaint village is where Vermont officially became a colony. After numerous protestations from the New York delegations, the Green Mountain region was granted statehood in 1791. With an active theatre playhouse and proud heritage association, it is a must-see for any American history buff.

The Dorset Historical Society Museum is a treasure trove of Americana. Tour exhibits feature artifacts and memorabilia from over 300 years of Dorset life.

A favorite summer spot for notable families, Abraham Lincoln’s son, Robert Todd Lincoln, set roots here at Hildene, The Lincoln Family Home. Built in the late 1800s and overlooking the Taconic Mountains, this architectural masterpiece hosts various events throughout the year.

Wilson House is a historic hotel that was once home to Bill Wilson, the founder of Alcoholics Anonymous. Designated on the historic registry, this colonial style Inn welcomes everyone to find serenity as part of their community.

The Dorset Theatre Festival aims to build an inclusive society through art and performance. It’s based on two pre-revolutionary barns, the perfect environment to relax. The company showcases plays, musicals, and seminars all year round.

Montpelier

The smallest state capital in the USA, Montpelier, founded in 1787, was recently voted one of USA Today’s 10 Best Towns in the Northeast for 2024. It is rich in the founding fathers’ history. Independently owned specialty boutiques are one of the reasons Montpelier has been continually recognized as the number one best small-town shopping destination in America. You can find everything from lavender-milled soap to hand-hammered copper pots along Main Street.

Maple is a staple in this town. In fact, some of the locals claim they have equal amounts of sugar as water in their bodies. One of the best ways to experience this yourself is to chill out at one of the many family-run farms. The Braggs have owned and operated the Maple Sugarhouse for eight generations. Open year-round, it offers tours and tastings.

Coburn Covered Bridge is Instagram story-worthy. Extended along the banks of the Winooski River, this 19th-century bridge is the last remaining in the town.

Book a relaxing stay at the over-two-century-old Inn at Montpelier. This boutique hotel has nineteen uniquely heritage-inspired decorated rooms with all the modern amenities. Within walking distance of shopping, dining, and activities, visitors can travel back in time without sacrificing the comforts of today.

Waitsfield

Named after Revolutionary militia General Benjamin Wait, this tiny hamlet sits in Washington County. Known for its two ski resorts, Waitsfield is a less hectic alternative to Stowe.

Known for its proximity to major ski resorts, Waitsfield offers a less hectic alternative to Stowe. Nearby, Sugarbush Resort in Warren is one of the largest in New England, offering extensive skiing and outdoor activities. Despite its modest beginnings in 1951, it employs over 30% of the town’s residents year-round.

Additionally, Waitsfield is home to Mad River Glen, a skier’s haven famous for its challenging trails and unique cooperative ownership. Both resorts offer a variety of outdoor activities throughout the year, making Waitsfield an excellent base for exploring the Mad River Valley.

During the warmer months, this area is ideal for fishing, swimming, and hiking. An ecological reserve, it is home to twenty-five different species.

The Mad River Path showcases crystal-blue falls and rock formations that locals believe hold indigenous spirits. The Round Barn Farm, built in 1910, is the perfect place to sit back and chill with a warm mug of cider. Throughout the year, it hosts numerous weddings and events, and guests can book extended stays in its wood-paneled, vaulted-ceiling accommodations.

Experience Vermont’s Timeless Charm

I doubt that anyone would argue with Pearl S Buck when she wrote that “all in all, Vermont is a jewel state, small but perfect.” One of the earliest settlements in the nation provides the ideal setting to chill and unplug. All year long, it falls under the trance of its cornucopia of color and its proud heritage. Relax against the backdrop of the Green Mountains and Winooski River. Compact but plentiful, Vermont offers endless opportunities to chill and so much more in 2024.