6 Storybook Towns In Vermont
Like other New England states, Vermont is celebrated for its natural beauty and storybook charms. From its highest summits to its coziest bed and breakfasts, the Green Mountain State caters to a range of travelers and itineraries, promising romantic getaways, rejuvenating day trips, and everything in between. Whether you are on the hunt for the perfect alpine hike, a secluded island adventure, or a historic downtown to explore with a cappuccino in hand, Vermont's small towns have it all—whatever your idea of storybook beauty may be.
Woodstock
Woodstock is one of Vermont’s best-known destinations thanks to its friendly locals, quintessential New England charms, and breathtaking natural surroundings. First chartered in 1761, the town was once a mill and factory hub in the mid-1800s, while present-day Woodstock is known for its tourism. With cities like Boston just three hours away by car, the Vermont village is a refuge from the hustle of urban life, promising a slower pace and authentic small-town feel. Whether hiking the Mount Tom Faulkner Trail for its vistas or sipping seasonal cocktails in a Victorian dining room at the Vic Tavern bar, good vibes are guaranteed.
Described as an “Enchanting Fairy Tale Town” by TheTravel in 2023, Woodstock, by all means, looks and feels like a New England village frozen in time. From living museums like Billings Farm to sites like the Historic Taftsville Covered Bridge, the past follows you throughout the town. Even Woodstock’s best outdoor attractions are sprinkled with history, like Marsh-Billings-Rockefeller National Historical Park. Vermont’s only national park, the area blends nature with the past in an enchanting way. Visitors can explore over 20 miles of tranquil forest trails, kept peaceful through the lack of bicycles or motorized vehicles. Tours of the Victorian mansion are equally enchanting, while its storybook gardens take the spotlight in the summertime.
South Hero
Similar to Woodstock, South Hero is frequently described as “Straight Out Of A Fairy Tale” due to its wineries, beaches, and orchards. Home to less than 2,000 locals, South Hero is set on the southern half of beautiful South Hero Island in Lake Champlain. Since it is a bit more sequestered, it is also quieter, offering the perfect escape for introverted travelers and those craving seclusion. While there are countless means of getting here, including driving or boating, the Island Line Trail is by far the most scenic. An adventure in itself, this 3-mile bicycle causeway offers breathtaking views of the surrounding scenes. Your journey ends with a ferry ride, carrying you and your bike the final 200 feet across the lake to South Hero Island.
Cycling is also a great way to explore the island itself, including storybook attractions like the Miniature Castles of South Hero. Designed as a tribute to his homeland, Swiss gardener Harry Barber built these whimsical castles on various properties across the island, many of which can still be viewed today. While outdoors, shores like White's Beach are great for relaxing. But the main way people unwind in South Hero is at its various orchards and wineries. Local favorites include spots like Allenholm Farm, Hackett's Orchard, and Snow Farm Vineyard and Winery, which is famous for its ice wine production.
Stowe
Beyond its reputation as a world-class ski destination, Stowe is also famous for its waterfalls and four-season mountain recreation. While winter is when this ski town shines, welcoming thousands to the Stowe Mountain Resort, this is just the beginning of what Mount Mansfield has to offer. As Vermont’s highest peak at 4,395 feet above sea level, this majestic summit boasts some of the prettiest hiking trails in the country. Stowe is a gateway to a range of picturesque alpine paths, like the Lake Mansfield Trail or the “Moderate but Marvelous” Stowe Pinnacle. From June through mid-October, Stowe’s Gondola SkyRide also offers a less strenuous way to reach the top of Mount Mansfield, paired with a bird’s-eye view of the landscape below.
While autumn is one of the best times to visit Stowe for its milder weather and beautiful foliage, spring is when its waterfalls take the spotlight. With the winter snowmelt and spring rain, cascades like Moss Glen Falls are at their most powerful. Falling 85 feet, Glen Falls is the tallest waterfall in Vermont. Luckily, even the least experienced hiker can reach this record-breaking landmark, the trail taking just 20 minutes to complete if you end your journey at the cascade. For a slightly more challenging hike with another rewarding waterfall, Stowe is also close to Bingham Falls, a 40-foot beauty attached to a majestic gorge.
Chester
About a two-hour drive south of Stowe, Chester offers a more laid-back energy centered around simple New England pleasures. The Windsor County town is more of an off-the-beaten-path destination, but its underrated nature keeps its small-village feel intact. For those familiar with its charms, it is a beloved weekend getaway spot known for its bed and breakfasts, antique shops, and historic landmarks. But even if you only find yourself in Chester for a day, you will leave feeling refreshed.
For those looking to spend the night, B&Bs like Franklyn Farm Inn offer a more rural retreat. Favoured for its pastoral surroundings and historical setting, the Inn was originally a 1700s stagecoach rest stop and tavern. Guests can explore its 35 acres of land, including a spring-fed pond, before going into town for Chester’s other attractions. Alternatively, Main Street B&Bs like Inn Victoria offer a more romantic setting in the heart of town. Built in 1851, the Victorian accommodation is near the town’s best locales and shops, like the Community Art Garden, Chester Bookworm, and Southern Pie Cafe. Antique shops like The Bargain Corner are also nearby, while historic attractions like the Stone Village Historic District are just three minutes away by car. The enchanting half-mile district is home to one of Vermont’s largest concentrations of historic stone structures, making it a must for any travel itinerary.
Montpelier
While we generally think of capital cities as bustling urban centers, Montpelier distinguishes itself as the smallest and quaintest state capital in the country. While the town of just 8,000 locals is home to significant structures like the Vermont State House, much of its identity is tied to its classic New England charms. For instance, travelers seeking Vermont’s famous maple syrup can find it in Montpelier at spots like Bragg Farm Sugar House or Morse Farm Maple Sugarworks. Montpellier is also home to charming landmarks like the Coburn Covered Bridge, a 19th-century bridge crossing the Winooski River.
While smaller than all other state capitals, Montpelier is still a spirited community with a lively art scene and exciting events. At the Lost Nation Theater, guests and locals alike can encounter world-class performances at an award-winning venue. The town is also home to countless art museums and venues, like the T.W. Wood Gallery & Arts Center and Artisans Hand Craft Gallery. As for events, Montpelier hosts a variety of festivals and celebrations throughout the year, including Art Walks on the first Fridays in February, April, June, August, October, and December. In October 2025, Montpelier will also host its annual Enchanted Forest event, welcoming autumn with music, storytelling, and candle-lit walks at Hubbard Park.
Shelburne
Located 7 miles from Burlington, Vermont’s top-populated city, Shelburne is a cozy lake town blending rural scenes and cultural attractions. The town is primarily known as the home of Vermont’s Shelburne Museum, the largest of its kind in northern New England. The 45-acre campus features 39 buildings, an operating vintage carousel, and over 100,000 items on display. Housing everything from French Impressionism works to American folk; this art and design museum is a must for any creative soul.
With Shelburne’s setting on the shores of Lake Champlain, outdoor recreation and postcard scenes are some of its other main lures. At Shelburne Bay Park, visitors can enjoy the over 1-mile waterfront overlooking Shelburne Bay, coupled with a 1.4-mile bike path and countless hiking trails across its 104 scenic acres. For a more unique day outdoors, Shelburne Farms is another top attraction. In addition to being a working farm, the 1,400-acre non-profit features over 10 miles of walking trails. The Farm Trail couples pretty pastoral scenes with gorgeous views of Mount Mansfield and the Green Mountains off in the distance, while woodland walks like the Butternut Trail are preferred for a more peaceful nature escape.
Final Thoughts
Vermont may be best known for its maple syrup, but the charm of the Green Mountain State runs far deeper than its famous sweet treat. There is something agreeably enchanting about the simple, timeless beauty found in Vermont’s towns. From charming covered bridges to peaceful rural trails, the state invites you to find joy in the small details we often take for granted. Even Vermont’s breathtaking mountain vistas have a way of slowing you down, encouraging a reconnection with nature and life beyond screens and daily stresses. Whether hiking to the highest peak in Stowe or sipping wine at a cozy South Hero winery, Vermont will inspire you to romanticize both the grand and the ordinary, making the world around you feel just a little more like a fairytale.
