6 Stunning Small Towns In Vermont
Vermont rewards travelers who slow down. South Hero opens onto the broad water of Lake Champlain and the islands beyond. Londonderry and Weston sit along Route 100 with Magic Mountain, Okemo, and the Green Mountain National Forest at their doorsteps. Bristol, Chester, and Montpelier round out the list with waterfalls, a historic "painted" village, and the smallest state capital in the country. These six Vermont towns each reward a long weekend.
Londonderry
Vermont Route 100, known as the "Skier's Highway," is a designated scenic byway that runs along the eastern side of the Green Mountains. Londonderry sits along the West River where it meets Utley Brook. Magic Mountain, on Glebe Mountain, still draws traditional skiers, and Lowell Lake State Park right outside town offers a quieter kind of outdoor day. A 3.5-mile loop circles the 102-acre lake, with fishing, canoeing, kayaking, and picnicking on the water and dense forest all around.
The Viking Nordic Center maintains groomed cross-country trails in winter, and Hamilton Falls sits a short drive away. The nearly 400,000-acre Green Mountain National Forest opens up more hiking and waterfalls. Heading west toward Bromley, travelers can stop at Taylor Farm for sleigh rides and farm-made treats.
Bristol
Bristol's annual Harvest Festival takes over the town green in late September with more than 65 craft vendors and exhibitors, kids' activities, food, and live music. The New Haven River runs through town and out through farmland in the foothills of the Green Mountain National Forest. East of downtown, the river drops roughly 10 to 15 feet at Bartlett Falls, which has a deep swimming hole and shallow wading areas.
Beyond the downtown's patriotic flags and old storefronts, Bristol has trails for a range of hiking levels. The Bristol Ledges Trail is a popular 3-mile loop that climbs to a cliff above town with views across the Champlain Valley. South of there, Bristol Cliffs Wilderness covers rougher terrain with unmarked trails, and its high points reach roughly 2,000 feet with views out to Lake Champlain and the Adirondacks.
Chester
Recognized as one of America's "Painted Places," Chester sits under tall maples and packs galleries, craft shops, and taverns into a small downtown, all within about 20 minutes of the Okemo ski slopes. The Stone Village Historic District on Route 103 preserves a 19th-century residential area built in a distinctive stone style. Depot Street runs south past the historic train depot, a red brick building dating to 1872.
Main Street mixes arts, antiques, and B&Bs like the Inn Victoria, a mid-19th-century building near the public Whiting Library's steeple. After breakfast at a local diner on a snowy morning, visitors can hit a nearby trail for hillside views, or take a class at Endless Creations Pottery Studio to bring home something of their own making. The feel is family-friendly with mountain scenery never far off.
Montpelier
Vermont's state capital since 1805, Montpelier is a compact, walkable city along the Winooski River near where it meets the Dog River. It is the smallest US state capital by population and is often noted as the only state capital without a McDonald's. The downtown fills with local restaurants and independent shops, and weekend parking is free. A good start: grab a coffee and join a free tour of the golden-domed Vermont State House.
The Greek Revival capitol, completed in 1859, presides over the historic district, with trails leading up through the century-old town green. The 190-plus-acre Hubbard Park holds a 54-foot observation tower at its high point. Nearby, Morse Farm Maple Sugarworks runs year-round with animals, gifts, and maple creemees, and the Lost Nation Theater keeps a full season of shows close to downtown.
South Hero
Reached via the scenic US-2, South Hero has a farmland feel and a downtown looking out over Keeler Bay and Kellogg Island. Pontoon rentals, kayaks, canoes, and fishing supplies are all available locally. Allenholm Farms offers apple picking, pies, and maple creemees, and Grand Isle State Park adds a sandy swimming beach, boat rentals, and campsites. Wally's Place is a local bagel shop that fuels most mornings.
The rest of South Hero unfolds as rolling farmland, apple orchards, and open country roads that suit a walk, a picnic, or a scenic drive. Keep an eye out for the "fairy castles," hand-crafted miniature stone castles built by Harry Barber, a Swiss immigrant, and now scattered on private properties around the island. Several sit near Snow Farm Vineyard along West Shore Road, which hosts craft wine tastings with lake views.
Weston
Weston preserves its 19th-century character in the foothills of the Green Mountains, with 3,343-foot Okemo Mountain rising just to the east. Route 100 runs past the Green Mountain National Forest, a route especially rewarding during fall foliage, and the village green sits framed by white clapboard homes.
The Vermont Country Store, founded in Weston in 1946, and the red Old Mill Museum perched over the West River are both village fixtures. The Weston Theater Company, one of Vermont's oldest professional theater troupes (founded 1937), draws strong audiences to its historic playhouse and the Walker Farm stage. Nearby, Weston Priory, a Benedictine monastery known for its singing monks, welcomes visitors year-round.
Plan A Vermont Weekend
Route 100 threads through the Green Mountains and links several of these towns directly, with Magic Mountain in the village of South Londonderry and Okemo at Weston's back. Chester's Stone Village, South Hero's country roads, and Weston's photogenic mill along the West River all reward a detour. For a central base, Montpelier makes an easy weekend of food, indie shops, and farm visits on the edge of town.
