10 Small Towns in Vermont with the Best Downtowns
Four-season natural beauty abounds in Vermont's small towns, not to mention historic significance dating back to the nation's early years and a level of sophistication that can only be found in New England. The best of these sweet spots offer a wealth of diverse experiences, whether visitors are seeking a serene oasis along the shores of the Deerfield River, art and culture amid the galleries of Brattleboro, or Colonial and Revolutionary War landmarks. Each of the following 10 towns makes a lasting impression in its own way, but if a vibrant downtown is a key factor for your next weekend getaway in Vermont, you'll find it on this list.
Montpelier
Montpelier snags the distinction of being the smallest state capital in the US, but it packs big character. Its downtown district centers around the golden dome of the State House, lined with independent shops, bookstores, and eateries. Here, visitors will find the cultural opportunities of a larger city in a hometown package. In spring and summer, the Capital City Farmers Market on State Street is a great way to meet locals, enjoy live music, and experience the community vibe.
In fall, the hills surrounding downtown offer ample hiking and leaf peeping, while winter adds a cozy ambiance to Montpelier’s many cafes and taprooms, such as Oakes & Evelyn, for modern farm-to-table fare, or the Three Penny Taproom, with fresh takes on classic pub fare that is especially enjoyable after snowshoeing or cross-country skiing through Hubbard Park.
Woodstock
Walking through the heart of Woodstock feels like stepping into a classic 19th-century painting. And with good reason: many of Woodstock’s shops, such as FH Gillingham & Sons, have roots going back generations. Visitors will enjoy the downtown’s historic facades and British colonial architecture, and unlike the covered bridges in most rural American settings, Woodstock’s Middle Covered Bridge spans the Ottauquechee River right in the center of town, so you can't miss it. Be sure to stop in at Unicorn and Woody's Mercantile for unique gifts to bring home, and dine at farm-to-table hot spots like highly-rated Au Comptoir or Sante, for seasonal small bites and carefully curated entrees.
Middlebury
This college town adds an intellectual flair to its classic New England village feel. Middlebury’s historic downtown is anchored by Middlebury College and Otter Creek, with no shortage of bookstores, boutiques, and cafes. Try Otter Creek Bakery’s artisan breads and pastries before browsing through Stone Mill Public Market’s multi-purpose spaces filled with local art, wine, and even lodging. Seasonal outdoor recreation is on tap year-round just outside Middlebury, and if the weather doesn't cooperate, you can always duck into the Henry Sheldon Museum for a taste of 19th and 20th-century life within its exhibits of furniture, paintings, and household objects.
Stowe
It doesn’t get more Vermont than Stowe! This mountain village oozes charm, and its walkable downtown is studded with historic buildings, artisan shops, and outdoor gear stores catering to the alpine crowd along the 5-mile Stowe Recreation Path. Under the backdrop of Mount Mansfield, Stowe is no stranger to tourism, popular for skiing and snowboarding in winter and hiking, biking, and paddle sports in the summer, all of which begin and end right in the heart of town.
Check out the Vermont Ski and Snowboard Museum to see which athletes the museum has honored and inducted into the Vermont Ski and Snowboard Hall of Fame each year, then linger to take in the sports photography of Hubert Schriebl. If you find yourself in Stowe in the autumn shoulder season, plan to check out the annual British Invasion, a three-day cultural celebration with a primary focus on classic British motorcars held over three days each September.
Bristol
Bristol isn’t afraid to break out of the quintessential New England mold, with plenty of architectural variety along its historic main street. Visitors will find late-19th-century buildings mixed with early-20th-century styles, making for an abundance of photo ops and scenic backdrops. Visitors won’t find any national chains within Bristol's downtown marketplace and shops, which celebrate local artists by offering handcrafted goods. Start at Art on Main, especially if you enjoy mixed media. In the center of town, the Bobcat Café & Brewery offers creative pub fare and craft brews, and the Bristol Harvest Festival on the town green draws a crowd each September. Come for the fresh local produce and stay for the musical talent!
Brandon
Visitors to Brandon won't have to choose between outdoor scenery and creative culture. This town north of Killington Resort is nestled in the foothills of the Green Mountains and is the home of the Brandon Artists Guild. In the artist-run gallery on Center Street, visitors can peruse the works of many local makers under one roof, from textiles and ceramics to painting, woodworking, and jewelry. The River Pub & Grill is a favorite watering hole with elevated pub food and views of the Neshobe River, while Café Provence serves casual European fare and also offers cooking classes for those keen to learn about the art of French cuisine.
Brattleboro
Foodies will want to take note of Brattleboro, an artistic and culinary hub on the West River. Known for one of Vermont’s most photogenic main streets, Brattleboro’s classic brick architecture pairs beautifully with its quirky museums and gallery scene. Start at the Brattleboro Museum & Art Center to enjoy contemporary art and exhibitions located in the town's historic train station.
Once you’ve worked up an appetite, stop in at Yalla Vermont, a beloved downtown eatery featuring Middle Eastern favorites that reflect Brattleboro’s culturally diverse and sophisticated palate. True to this reputation, Brattleboro’s farmers market is open from late spring to fall and features global foods, as well as handmade crafts each week. And for those seeking something a little different, Brattleboro is home to the Vermont Circus Festival each November, hosted by the New England Center for Circus Arts, which also offers workshops and performances throughout the year.
Chester
Those looking for that classic storybook New England aesthetic will find it in Chester, with historically preserved stone buildings throughout its downtown district. A strong antique culture resides here, so be sure to stroll Chester's many vintage shops, including Stone House Antique Center, which boasts 20,000 square feet of floor space filled with fine furniture, folk art, quilts, and collectibles. Next, get an energy boost in the form of a sugar rush at Sugar Bob’s Finest Kind Store, specializing in Vermont’s favorite export: maple syrup and maple-flavored candy. The Chester Festival on the Green is prime time to visit, when the town comes out in full force to celebrate all things autumn with crafts, music, and local food.
Waitsfield
The tiny town of Waitsfield found its place on the map as the birthplace of Green River Coffee Roasters and lies in the heart of the Mad River Valley, where plenty of seasonal outdoor recreation awaits. Downtown meanderers will enjoy the historic commercial zone of Bridge Street, which culminates in the Mad River Green. This central meeting point comes alive with artisans and live music during the summer months. Be sure to stop in at the Madsonian Museum of Industrial Design, a truly unique museum celebrating the artistry and innovation behind common everyday objects, then take a stroll across the Historic Waitsfield Covered Bridge, one of the oldest in the state and the ideal spot for your perfect vacation photo.
Wilmington
Located in the rolling, forested hills of Southern Vermont, Wilmington’s lively downtown promises visitors enough artisan shops, eateries, and seasonal markets to make a long weekend fly by. Main Street is lined with antique shops and local art galleries, including 1836 Country Store, which is actually on the National Register of Historic Places. Pick up some staples here, such as maple candy and a coffee mug or two.
Every autumn, the main drag of Wilmington is framed by pops of fall color, adding to the town's picture-perfect allure, and in summer, fishing on the Deerfield River is a popular draw, while nearby Mount Snow offers year-round outdoor recreation. No matter the season, don’t miss La Casita Taqueria y Mas, Wilmington’s welcoming downtown Mexican-inspired restaurant, for authentic flavors in a warm and friendly atmosphere.
Vermont's Best Downtowns Come in Small Packages
These 10 Vermont downtowns add plenty to any itinerary, winter, spring, summer, or fall. Cue up whichever classic New England experience most appeals, whether that places you steeped in American history, lost in the aisles of artisan shops and galleries, or taking in the fresh mountain air. You can't go wrong while visiting Vermont.
