Vermont’s small towns deliver postcard scenery in every season, and you don’t have to travel far to find one. Stowe has gondola rides at Stowe Mountain Resort and paddleboarding at the Waterbury Reservoir. Montpelier, the state capital, fits a statehouse, a walkable downtown, and a hilltop park into a population of just over 8,000. Richmond anchors the Winooski River valley around an unusual 16-sided church. Seven towns stand out as Vermont’s prettiest.

Bennington

Often cited as the first town chartered in what became Vermont (1749), Bennington pairs a red-brick downtown with the hills of the Green Mountain region in southern Vermont. Streets fan out from the Bennington Battle Monument, a 306-foot stone obelisk that marks a pivotal Revolutionary War engagement. Covered bridges and Victorian architecture like the Park-McCullough House give the town visual range across the year. Bennington is best known for its autumn colors, but winter brings snow-dusted pines and a quieter version of the same scenery.

Montpelier

Montpelier is Vermont’s capital but also the least populous state capital in the country, with just over 8,000 residents. That scale is the point. The Greek Revival State House sits at the edge of a compact downtown of locally owned businesses, and Hubbard Park climbs the hill behind the capitol with trails for hiking and cross-country skiing. Montpelier is also the only U.S. state capital without a McDonald’s. The Winooski River runs through town, and you can walk from a statehouse tour to a riverbank bench in about ten minutes.

Richmond

Vermont gets most of its attention in autumn, and Richmond is no exception, but the town is arguably better in winter. Cochran’s Ski Area, a small family-run hill just outside downtown, has been a community fixture since 1961 and still runs on affordable lift tickets. The Winooski River bisects Richmond, and the surrounding trail network turns quiet and cinematic under snow. The town’s signature building is the Old Round Church, which despite the name is a 16-sided meetinghouse from 1812.

Stowe

If any Vermont town has a reputation for winter, it’s Stowe. Stowe Mountain Resort is the state’s most famous ski destination, and the gondola runs year-round for aerial views of Mount Mansfield and the Green Mountains. In warmer months, the Stowe Pinnacle trail climbs to one of the most photographed viewpoints in the state, with the summit sitting at roughly 2,660 feet above sea level. The village has a small but active art scene, with galleries along Main Street showing regional painters and craftspeople alongside traveling exhibitions.

Waitsfield

Waitsfield sits along Scenic Route 100 in the Mad River Valley and bills itself as a year-round outdoor destination. Sugarbush Resort, just down the road, is the draw in winter, with skiing and snowboarding on Lincoln Peak and Mount Ellen. The trail network is just as active in summer for hiking and mountain biking. The town itself keeps things low-key: a covered bridge on Bridge Street, a few restaurants along Route 100, and the Mad River running through the middle of it all.

Wilmington

Route 9 through southern Vermont, also known as the Molly Stark Scenic Byway, runs straight through Wilmington in the heart of the Green Mountain National Forest. The Hogback Mountain Conservation Area nearby covers roughly 600 acres of protected land with wide views across southern Vermont. Mount Snow handles most of the local skiing and has an active summer mountain-biking program. The best-known spot in town is Dot’s Restaurant, a diner that was washed out by Tropical Storm Irene in 2011 and rebuilt with community funding. It reopened in 2014 and still serves the same blueberry pancakes.

Woodstock

Woodstock plays the same showpiece role for central Vermont that Bennington plays for the south. The Federal-era downtown wraps around a town green, and the Middle Covered Bridge carries foot and vehicle traffic over the Ottauquechee River right at the edge of it. Billings Farm & Museum operates as a working Jersey dairy and runs seasonal demonstrations of traditional farm work, including sheep shearing and plowing with draft horses. Just up the road, the Marsh-Billings-Rockefeller National Historical Park is the only national park dedicated to conservation history.

Vermont’s Prettiest Small Towns Reward A Slow Visit

For scenic small towns, Vermont covers a lot of ground. The seven above offer historic architecture, mountain access, and enough variation in season and setting to make repeat visits worthwhile. Drive between them on Route 100 or Route 9 and you’ll pass a dozen more that could just as easily have made the list.