Summary
New England is renowned for its natural beauty, and Vermont particularly excels in this regard. There is an enchanting charm about Vermont that is undeniably appealing. Filled with small towns, each typically features a village center, a Main Street, historic architecture, distinctive boutiques, and local businesses that encapsulate its community spirit. Throughout the year, visitors can appreciate the outdoors, exquisite cuisine, and the best offerings of New England.
Let us examine the most charming small towns to visit in Vermont:
1. Chester
Chester holds the unique distinction of housing two areas listed on the National Register of Historic Places. Stone Village, named for its granite structures, and the Chester Historic District are both imprints of colonial architecture reflecting an early American New England aesthetic.
This town often serves as a launchpad for outdoor expeditions to nearby Mount Killington, Okemo, and Mount Snow. Both adventurers and relaxation seekers appreciate Chester’s small-town ambience while benefiting from the nearby resorts and parks.
One popular activity is embarking on a scenic voyage aboard the Green Mountain Flyer Scenic Railroad, offering breathtaking views from start to finish. While in Chester, be sure to visit the Stone House Antique Centre, Da Vallia Art, and the Vermont Institute of Contemporary Arts.
2. Woodstock
Woodstock has established itself as a favored tourist destination over the years, allowing it to refine the quintessential Vermont experience. The town masterfully blends charm and sophistication to provide a necessary getaway with ample amenities. Its boutique and antique shopping are among the finest in the state, complemented by exceptional dining options and a plethora of entertainment.
History enthusiasts will appreciate the Billings Farm and Museum. Previously owned by Laurence and Mary French Rockefeller, this now dairy farm features a restored late 19th-century farmhouse, both recognized as National Historic Landmarks. Art aficionados will enjoy visiting various galleries, particularly the Stephen Huneck Gallery, while culinary enthusiasts should not miss F.H. Gillingham & Sons, a must-visit general store and gourmet shopping experience.
3. Montpelier
Montpelier, Vermont, is distinguished as America’s smallest capital. Among residents (who all consider themselves locals), it is celebrated for its numerous farm-to-table restaurants and daily farmers market.
As the state’s government hub, Montpelier offers a little bit of everything. Key attractions include the Vermont Historical Society Museum, the state house, Hubbard Park, the New England Culinary Institute, and T.W. Wood Art Gallery.
This is merely the beginning! Despite its small-town character and the warm hospitality accompanying it, Montpelier possesses a vibrant cultural scene, making it truly exceptional.
4. Brattleboro
Situated in the southern part of the state, Brattleboro boasts a unique artsy character that draws visitors from near and far. It’s a pedestrian-friendly town with an abundance of clubs, restaurants, studios, galleries, and shops, all harmoniously coexisting with the beauty of nature.
Regardless of your location in Brattleboro, stunning mountain or river views are a constant presence. While strolling through the town, an unexpected street performance could provide delightful entertainment, complemented by independent bookstores, record shops, and artisanal boutiques.
The town features several theaters, many with significant historical relevance. Every month, visitors can partake in the First Friday Gallery Walk, and nearly every restaurant showcases local artists. Brattleboro fosters an atmosphere that guarantees lasting memories.
5. Putney
A short distance from Brattleboro lies Putney, which embodies a similar yet even more relaxed atmosphere. Visitors can explore local spinnery, berry and apple orchards, and a winery while savoring tranquil walks and refreshing breaths.
This town possesses an aura that makes you want to keep it a secret, wishing to preserve its pristine character. Sacketts Brook maintains its original stone arch bridge that flows through the municipal heart. The Putney general store and co-op serve as community cornerstones, encapsulating its charm.
6. Lincoln
At the base of Mount Abraham lies Lincoln. The natural environment surrounding the New Haven River is truly breathtaking. Residents take pride in the scenic beauty of the local farms and forests. Originally settled by Quakers in the late 18th century, Lincoln now supports a population of approximately 1,200.
Lincoln is particularly renowned for its distinctive treehouse, constructed across four gigantic maple trees and standing 30 feet above the ground. Guests can enjoy a stay for $150 per night, equipped with heating, a shower, electricity, and even a mini-fridge. Don’t overlook the Old Hotel, local general store, and Burnham Hall during your visit.
7. Bristol
Bristol is a haven for festival enthusiasts. The town celebrates a variety of events, with many visitors flocking for the Outhouse Race, known as the longest-running event of its kind in the United States. The entire downtown area is designated a National Historic District, allowing visitors to experience a sense of stepping back in time.
Located in the foothills of the Green Mountains, Bristol serves as an ideal getaway destination. Visitors express admiration for the village shops and the genuine friendliness of the locals. If visiting in June, don’t miss the Pocock Rocks Street Fair or the Bristol Band summer concerts, which have been a staple since the end of the Civil War.
8. Stowe
Regardless of the season, Stowe stands out as a premier destination in Vermont. Thanks to the Stowe Mountain Resort, countless opportunities for outdoor adventures await. Mount Mansfield, the tallest peak in Vermont, serves as a sanctuary for nature enthusiasts. Whether skiing, hiking, or repeating visits to experience both, Stowe satisfies all.
The village itself boasts a history spanning 200 years. In the downtown area, visitors can find museums, galleries, theaters, outdoor film festivals, the Vermont Ski and Snowboard Museum, and numerous fine dining establishments. With its year-round appeal, Stowe is undeniably a must-visit destination.
9. Waterbury
Waterbury is a favored retreat for Vermonters seeking a reprieve. Often described as a charmingly relaxed town, it embodies a low-key, unpretentious atmosphere. Local pride centers around superb, locally-sourced dining options.
The town undeniably represents the pinnacle of Vermont’s offerings. Owing to its remarkable natural landscapes, Waterbury frequently serves as a sought-after wedding destination. For premier accommodations, consider Groenberg Haus, a hillside chalet featuring a stone hearth and grand piano.
10. Shelburne
For those seeking luxury, Shelburne on the shores of the picturesque Lake Champlain is the ideal destination, serving as a suburb of Burlington. Visitors come to indulge and enjoy upscale experiences. The town is home to the Shelburne Museum, Shelburne Farms, and the Vermont Teddy Bear Company, making it an excellent family-friendly location.
The farm features a guest house with 100 rooms, a five-story barn, hayrides, and an exceptional hiking trail. At the museum, you can witness live demonstrations of printing, blacksmithing, and weaving. The lakeside beach provides a delightful summer escape, while various rental companies offer boat rentals. If visiting during apple season, be sure to stop by Shelburne Orchards for the finest apples and cider in Vermont.
11. Manchester
Attention shoppers! Do not overlook the factory outlets and exceptional shopping experiences available in Manchester. This town attracts New Yorkers and Europeans alike, drawn by its selection and value. From high-end retail to charming boutiques and remarkable bargains, shopping here is an engaging experience.
In addition to shopping, Manchester boasts a vibrant cultural scene. Visitors can enjoy concerts, galleries, theaters, history, craftsmanship, and exquisite dining. The ambience of the village seamlessly blends cultural sophistication with old-world New England charm, offering an unforgettable experience from start to finish.
12. Grafton
Historically, Grafton served as a major stagecoach stop between Albany and the Green Mountains, welcoming visitors for nearly two centuries. Nestled in the mountains, many original buildings have been revitalized to offer an authentic New England atmosphere.
As you explore downtown, you may feel as though you are traversing a living museum. In winter, the snow-covered mountains create a unique and enchanting ambiance that is characteristic of Grafton. The town’s 600 residents actively participate in community meetings, working collaboratively to maintain a vibrant and welcoming community.
13. Grand Isle
Grand Isle spans roughly 35 square miles, with nearly 19 of those consisting of water. Situated in the Islands and Farms region of Vermont, it is primarily a fishing town. This area houses the Ed Weed Fish Culture Station, one of only five such facilities in the state. Moreover, the oldest log cabin in New England, Hyde Log Cabin, was constructed in the late 18th century and housed the Hyde family for over a century and a half.
The most frequented state park is located in Grand Isle, which also ranks as the second largest in Vermont. It offers RV camping and primitive camping options. The experiences available here differ from the rest of the state, characterized by abundant water and a notable fishing culture. Therefore, adding Grand Isle to your itinerary is essential to appreciate its unique offerings.
14. Charlotte
Charlotte is synonymous with the Champlain Valley. Established in the late 18th century, this thriving town is primarily agricultural. Orchards, dairies, sugarbushes, berries, honey, livestock, and grains are all flourishing economic enterprises. Notably, Charlotte also boasts a winery that receives accolades from visitors.
Mount Philo State Park, named after its nearly 1,000-foot peak, is a popular destination featuring magnificent vistas, trails, and a nearby wildlife refuge.
15. Craftsbury
Imagine rolling hills, picket fences, family-run farms, and lush green forests. This picturesque scenery typifies Craftsbury, Vermont. The town consists of five villages, with a combined populace of approximately 1,200, capturing the essence of classic Americana.
Engage in cross-country skiing and snowmobiling during winter, partake in maple sugaring rituals in spring, attend the Antiques and Uniques Festival in July, and marvel at the stunning fall foliage each autumn.
