7 Prettiest Downtown Strips In Vermont

Vermont's prettiest downtown strips capture New England history through brick facades and historic churches, all set against the surrounding rolling mountains. These towns stand out in every season, from winter months when big, fluffy flakes fall in ski towns like Stowe, to autumn when surrounding mountains like Deer Leap turn red and gold, to springtime when the state's famous green mountains erupt with foliage. Local cheese shops, covered bridges, and long-standing inns make these seven Vermont downtowns a worthy day trip or weekend visit.

Bristol

Local pride and natural beauty combine to give Bristol a quintessential New England Main Street. Backed by Deer Leap Mountain and lined with flat-topped brick buildings that house thoughtful shops and services, Bristol's Main Street is a destination for many in every season. Stopping in at the Vermont Marketplace is a must, where a variety of local goods like jams, syrup, baked goods, chocolate, and teas can be found, along with gifts like clothing, blankets, jewelry, and books. For a small town (population about 3,800), there are some great choices for dining, including Cubbers for pub fare or the Tillerman for wood-fired pizza. The center green space features a gazebo that hosts various musical acts, and every year, Bristol hosts its Harvest Festival, where more than 70 vendors sell their art, food, and crafts.

Chester

Located in southern Vermont, Chester's main street is known for its preserved 19th century stone buildings, the Stone Village Historic District with a number of substantial pre-Civil War houses built of stone from local quarries, and the popular Chester Festival on the Green. In winter, skiers from Okemo Mountain stop in Chester to visit some of Main Street's famous restaurants, including the Scottish-inspired fare at MacLaomainn's Scottish Pub, or the pies and sandwiches at Southern Pie Café. Around Christmas time, the entire town gets together for the annual tree lighting ceremony at the town green, and Main Street and the Stone Village are adorned in hundreds of thousands of lights, creating a vibrant Christmas theme on one of the prettiest main streets in the state.

Weston

What it lacks in size, Weston makes up for in style. This town of just more than 600 people is located in central Vermont and is home to the Weston Theatre Company, the anchor of the town's Main Street. It's the state's oldest professional theater and hosts Broadway musicals, local productions, and musical talent. Main Street's architecture is defined by preserved, colorful, classic structures like the Vermont Country Store and white-steepled churches, and the entire village is listed on the National Register of Historic Places. The Left Bank offers some of the best fine dining in the area with warm ambiance and incredible service, while the Vermont Cheese Emporium is a retail shop with a wide variety of local artisanal cheeses.

Waterbury

If you stand on Waterbury's Main Street and close your eyes, it's not hard to picture times past where horse-drawn carriages filled the streets and people in 1800s period clothing browsed the storefronts. The street's historic low-rise buildings range from Federal and Greek Revival commercial buildings to Italianate and Victorian residential styles. Key landmarks include the historic brick Waterbury State Office Complex, the Waterbury-Stowe Railroad Station built in 1875, and the former Green Mountain Seminary. Main Street is lined with numerous popular, high-quality dining options set in some of these historic structures, including Hen of the Wood, a renowned rustic farm-to-table restaurant, Prohibition Pig, famous for its barbecue, and The Reservoir, a tap room with a large, often-updated beer list.

Middlebury

Historic buildings, a college-town atmosphere, and waterfalls make Middlebury's main street one of the most distinctive in the state. Home to about 9,000 people, Middlebury is where nature and town pride collide, creating a vibrant, upbeat atmosphere. Middlebury Falls cascades over a dam before continuing down Otter Creek, setting the tone for the downtown area. Grabbing a sandwich at Costello's and sitting by the falls is a popular pastime for Middlebury College students, followed by a walk along Main Street, which is full of shops like The Vermont Book Shop or Addison West, which is full of Vermont-inspired home decorating ideas. Main Street's commercial Victorian and brick-block construction is the result of an 1891 fire that led to the reconstruction of the street with large, fireproof blocks and stone accents that make Middlebury's buildings unique.

Stowe

Stowe's Main Street is most beautiful when large, fluffy snowflakes tumble from the sky, and skiers and snowboarders can't help but smile. This ski town is instantly recognizable by the Stowe Community Church's steeple, which was completed in 1863, and many of the other buildings have been maintained to reflect their historical roots. Stowe blends mountain scenery with classic Federal and Greek Revival architecture, historic centerpieces like the Green Mountain Inn and Akeley Memorial Building, and numerous dining options to feed hungry skiers like Harrison's Restaurant on Main Street or Lower Bar, which features big, delicious portions and fantastic service. Just a few steps off Main Street is the Gold Brook Covered Bridge, a Howe truss bridge built in 1844.

Montpelier

Montpelier is Vermont's capital and the smallest state capital in the U.S. with a population of about 8,000. As might be expected for a capital, Main Street is lined with state government buildings, mostly influenced by Richardsonian Romanesque architecture, including the Department of Agriculture building. The Vermont State House, completed in 1859, features an unmistakable golden dome and granite façade, part of its Greek Revival influence. The street's civic feel is offset by farm-to-table restaurants like Oakes & Evelyn or Sarducci's Italian restaurant, situated along the Winooski River. For a small town, Montpelier stands tall with rich history, a vibrant main street, and important civic responsibility.

Postcard Perfection Awaits

Vermont towns are known for their warm and friendly locals and scenery that holds up no matter the season. From an iconic ski town like Stowe, where architecture, history, and recreation blend to create a singular atmosphere, to Montpelier, where civic duty is offset by farm-to-table restaurants, a river running through the downtown, and historical buildings, every Main Street here is worth discovering.