7 Cute Small Town Drives In Vermont

Covered bridges and mountain roads climbing toward places like Mount Mansfield make Vermont especially rewarding to see by car. From brick storefronts in Morrisville to the marble history of Dorset and Danby, these drives pass through the kinds of small towns that give the state its character. The scenery shifts with the season, but these routes offer plenty in any month, whether that means stopping at the Warren Store, looking out over Quechee Gorge, or simply following the road into quiet village centers and local shops. Together, these seven drives trace some of Vermont’s most memorable small-town roads.

Stowe, Elmore, and Morrisville

Distance: 20 miles | 35 minutes

This route through northern Vermont takes roughly 35 minutes and covers about 20 miles, but allow extra time to enjoy the stops, as there is plenty to see and do.

Start in Stowe, a well-known mountain town situated at the base of Mount Mansfield, Vermont’s highest peak, where the town offers activities for every season. In winter, visitors can take advantage of the area’s ski resorts, go snowshoeing, try dog sledding, or enjoy a traditional horse-drawn sleigh ride. Winter is also a wonderful time to experience the Stowe Winter Carnival, which features ice carving and family-friendly events.

During the warmer months, explore Smugglers’ Notch State Park or ride the gondola up Mount Mansfield for great mountain views. In the fall, local cideries and maple sugar houses offer seasonal treats, while the village center remains lively year-round with cafés, boutiques, and mountain-rustic architecture.

If you are visiting between late May and mid-October and the weather cooperates, consider adding 4.5 miles to your trip by driving the Mount Mansfield Auto Toll Road, which climbs to roughly 3,850 feet. From the summit area, short walking trails provide sweeping views across Lake Champlain and the Adirondack Mountains.

Continuing through the Green Mountains brings travelers to Elmore, a quiet town near Lake Elmore and Elmore Mountain. The drive ends a short distance away in Morrisville, a historic village in the Lamoille Valley known for its brick storefronts and relaxed rural atmosphere. Together, these communities offer a perfect introduction to northern Vermont’s mountain scenery.

Waitsfield, Warren, and Granville (Route 100)

Distance: 25 miles | 40 minutes

Running along Route 100 for roughly 25 miles (about 40 minutes), this drive explores the heart of the Mad River Valley, one of Vermont’s most scenic rural regions.

Begin in Waitsfield, a village known for its covered bridges, pastoral farmland, and local markets. Heading south, the road passes through Warren, a mountain community located near Sugarbush Resort. While passing through Warren, consider stopping at the historic Warren Store, a beloved general store dating back to 1839 that serves homemade baked goods, sandwiches, and classic Vermont maple treats.

As the drive continues south toward Granville, the landscape becomes increasingly quiet and forested. If time allows, consider stopping at Moss Glen Falls, right off Route 100 near Granville, one of Vermont’s most picturesque waterfalls. The peaceful mountain town of Granville provides a tranquil end to this scenic stretch of Route 100.

Woodstock, Quechee, and Hartland

Distance: 16 miles | 25 minutes

This countryside drive stretches about 16 miles and takes roughly 25 minutes, linking several historic communities in central Vermont. Just outside Woodstock, a short detour to Sleepy Hollow Farm in nearby Pomfret reveals one of the most photographed properties in Vermont. During peak foliage season, however, the road is sometimes restricted due to heavy tourism, so visitors should check local guidelines and respect road closures when applicable.

From there, head south to Woodstock, often considered one of the most beautiful villages in New England. Its historic village green, covered bridges, and elegant architecture attract visitors throughout the year, though the town becomes particularly busy during the autumn foliage season.

A short drive east leads to Quechee State Park, where trails overlook the dramatic Quechee Gorge, often called “Vermont’s Little Grand Canyon.” Finish the drive in the quiet town of Hartland, where the picturesque Martin’s Mill Covered Bridge sits just off Route 5.

Manchester, Dorset, and Danby

Distance: 17 miles | 25 minutes

This drive through southern Vermont takes only 25 minutes and covers about 17 miles, with a range of stops along the way. This route begins in Manchester, where every season brings something different. In winter, either Stratton Mountain or Bromley Mountain offers ample skiing and snowboarding, while those in search of a calmer pace can enjoy a serene winter sleigh ride. Throughout the year, visitors can explore Manchester’s boutiques, historic inns, and galleries, with easy access to nearby hiking trails. A local highlight is Hildene, the historic Lincoln family estate built by Robert Todd Lincoln, which features beautiful grounds, gardens, and architecture, framed by sweeping mountain views.

Fishing enthusiasts may want to visit the American Museum of Fly Fishing, which explores Vermont’s fly-fishing past with an impressive collection of historic rods, reels, and artwork.

A few miles north in Dorset, you will find a town whose history is deeply entwined with the Dorset Quarry, the oldest commercial marble quarry in the United States. Finish your day by driving over to Danby, another marble town surrounded by forests and mountains, with over 36 miles of winding, tree-lined roads, where the quiet pace of Vermont becomes apparent.

Bennington, Arlington, and Sunderland

Distance: 21 miles | 25 minutes

This scenic drive along Route 7A covers about 21 miles and takes about 25 minutes, connecting several historic towns along the Taconic Mountains. Start in Bennington, where the tallest manmade building in Vermont, the 306-foot Bennington Battle Monument, can be reached by elevator and offers spectacular views of the town and surrounding countryside. Literary enthusiasts will appreciate a visit to the Old First Church, adjacent to the Bennington Centre Cemetery, the resting place of Robert Frost. Other attractions include the Robert Frost Trail, the Park-McCullough Historic House, covered bridges, local museums, and galleries.

From there, continue north to Arlington, a town that once inspired Norman Rockwell with its white church steeple and traditional New England homes.

The drive ends in the tiny mountain community of Sunderland, surrounded by forested hills. Nearby, the Mount Equinox Skyline Drive offers wide mountain views, especially during fall foliage season (though tickets can only be bought between Memorial Day weekend and October 31).

If you have additional time, a short detour north will bring you to the Lye Brook Falls, one of the highest waterfalls in Vermont. The hike typically takes about two to three hours round-trip but rewards visitors with a dramatic 125-foot waterfall.

Chester, Weston, and Londonderry

Distance: 17 miles | 25 minutes

This drive links several small villages and spans about 17 miles, taking roughly 25 minutes. Start in Chester, known for its Stone Village District, where 19th-century stone buildings line the street. While there, explore local galleries, browse one of the many antique shops, or hike the Lost Mine Trail.

A short drive west to Londonderry, then north on Route 100, will bring you to Weston, home to the Weston Playhouse, Vermont’s oldest professional theater, which still puts on high-quality performances, and the iconic Vermont Country Store. Just north of the town sits the Weston Priory, a Benedictine monastery known for its tranquil setting and small shop selling handmade crafts and baked goods made by the monks. Finish your drive in Londonderry, a quiet mountain town with many outdoor trails and recreation opportunities. Before leaving, visitors often recommend going to Taylor Farm, a small local dairy known for its artisanal cheeses and maple products.

Brattleboro, Wilmington, and Dover

Distance: 27 miles | 40 minutes

This drive into Vermont’s southern mountains covers about 27 miles in roughly 40 minutes. Start in Brattleboro, a town rich in culture along the Connecticut River, known for its galleries, bookstores, and lively art scene. From there, the drive climbs toward Mount Snow. Consider stopping at the Hogback Mountain Conservation Area, as the overlook offers sweeping views of Vermont, New Hampshire, and Massachusetts on clear days.

Continue on to Wilmington, known for its historic brick buildings and a downtown along the North Branch of the Deerfield River. The route finishes in Dover, a small alpine town at the base of Mount Snow. In the winter, it is particularly popular for its ski resorts, but in summer through fall, the hiking trails and mountain views are well worth the trip.

Vermont’s small towns, winding country roads, and mountainous views make it an ideal place for a scenic drive at your own pace. These seven drives showcase some of the many small towns scattered across the Green Mountain State, each offering a different mix of outdoor adventure, historic villages, tranquil countryside, and local art. Whether visiting during peak foliage season or exploring on a quiet summer afternoon, these routes invite travellers to slow down and experience the landscapes and small towns that make Vermont such a memorable destination.