Vermont's most enchanting small towns for a magical trip

Fairy-tale New England towns

Journeys through Vermont have a special storybook quality – scenic routes wind through wild forests and mountain valleys, or across old wooden bridges to river mills and heritage towns. In contrast to its epic landscapes, Vermont’s urban centers are tiny – even state capital Montpelier has a small-town feel. But each settlement is rich with history and tradition.

Here, we’ve rounded up the region’s most charming towns, a string of which can be visited on your own fairy-tale adventure.

Weston, Windsor County

Weston oozes old-world charm with quaint village stores and galleries, clapboard houses and a parish church knitted into a pastoral setting of watermills, waterfalls and forests. Catch a local performance at the Weston Theater Company and then use the town as a springboard for exploring the Green Mountain National Forest. 

Waits River, Orange County

The picture-perfect village of Waits River is so enchanting that it features on postcards and even jigsaw puzzles. And if you're in eastern Vermont, it’s well worth making a detour to snap your own photos, especially in fall when the surrounding canopy explodes in red and gold. Though tiny, the riverside settlement of cute barns and homesteads has a striking white Methodist church and its vintage schoolhouse is listed on the USA's National Register of Historic Places.

Chester, Windsor County

A classic New England village chock full of traditional shops selling arts and crafts and local produce, Chester dates back to the 1700s and its Stone Village Historic District and Chester Village Historic District preserve many of its architectural treasures. But the town is more than just a pretty place: it also hosts festivals celebrating Vermont culture, including the Winter Carnival, Chester Fall Festival and the Big Buzz Chainsaw Carving Festival.

Brattleboro, Windham County

With a downtown stuffed with interesting independent stores, coffee shops and architectural gems such as the Creamery Covered Bridge (pictured), Brattleboro has more than its fair share of New England charm. Originally growing up around the Connecticut River, it was once a manufacturing center and its old converted mills still hug the riverbanks today, reinvigorated by a thriving arts community. Among the notable buildings nearby is the former lodge of famous writer Rudyard Kipling.

Manchester, Bennington County

This must-visit town in southern Vermont exemplifies the gentle rhythm of the state's small-town life. You can browse book stores and craft shops, gaze on pretty steeples and visit the historic Lincoln family estate of Hildene. Art lovers should stop in at Manchester’s Southern Vermont Arts Center, which features an outdoor sculpture park.

 

Dorset, Bennington County

A gorgeous little town of white wooden clapboard houses, traditional stores and sleepy streets, Dorset is pocket-sized but perfectly formed. A gleaming man-made marvel filled with water, the nearby Dorset Marble Quarry was the first of its kind in the US, supplying the stone for notable buildings including the New York Public Library. The quarry is now popular with sightseers and local cliff-jumpers. Dorset is also a gateway to Emerald Lake State park, where you can go kayaking and hiking.

Bennington, Bennington County

History-rich Bennington was founded more than 250 years ago close to the site of an important battle in the American Revolutionary War, today commemorated by the 305-foot Bennington Battle Memorial. Among the many preserved buildings is the Park-McCullough Historic House, one of the best examples of Victorian architecture in the whole of New England. It’s also something of a hub for covered bridges with five photogenic crossings within an easy drive.

Grafton, Windham County

Perhaps the prettiest town in all of southern Vermont, Grafton is nestled in the Green Mountains and is still picture-perfect thanks to a careful restoration program established in the 1960s. Steeped in history, the Grafton Inn at the center of the town is one of the oldest still-open inns in the US. In winter it makes a magical setting for activities like snow-shoeing and cross-country skiing, while the Grafton Trails and Outdoor Center offers biking and hiking in the warmer months.

Montpelier, Washington County

The USA's smallest state capital (by population) is more town than city, with its permanent residents numbering no more than 8,000. It's got a compact center too: walk its historic downtown district lined with cute cafés, bookstores and independent shops, dip into its thriving theater and arts scene or brush up on the region’s history at the Vermont State House and Historical Society Museum.

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Jericho, Chittenden County

It’s worth visiting Jericho just to see its gorgeous old red stone mill perched precipitously over a rocky gorge (it's now the base for the Jericho Historical Society). Be sure to check out the Jericho Center Country Store, too, which is one of the oldest of its kind in Vermont. Another highlight is Galusha House, former home of the namesake Vermont governor, which was built in 1790 and is listed on the USA's National Register of Historic Places.

Shelburne, Chittenden County

This waterside town rounds the shore of Lake Champlain and is almost an extension of Burlington, though it has a charm all of its own. At Shelburne Farms, visitors can taste the finest local maple syrup and Vermont cheeses, while the enormous and fascinating Shelburne Museum is housed in heritage buildings and stuffed with historic artifacts, art and Americana. Check out the beautiful old paddle-wheel steamer that's dry-docked outside.

Stowe, Lamoille County

The hills are alive with the sound of music in Stowe, which was home to the von Trapp family after they escaped Austria during the Second World War. Today travelers can stop by the Trapp Family Lodge and even stay the night. Tucked beneath Vermont’s highest peak, Mount Mansfield, Stowe’s quaint storefronts and homesteads, white-steepled church and magical mountain views make it a classic New England town. For outdoorsy types and hikers the town is a gateway to Smugglers' Notch State Park.

Waitsfield, Washington County

A picturesque town arranged along a meandering river with a cute covered bridge, Waitsfield shelters in a verdant valley between the Green Mountains and the Northfield range. It's traditionally a farming community and its gorgeous 150-year-old farmsteads now house cozy B&Bs, while visitors will find craft beer spots such as Lawson's Finest Liquids. The town is also a hub for outdoor sports including skiing during the wintertime.

Essex, Chittenden County

This pocket-sized city of handsome red-brick buildings is smaller than many towns, but it’s home to the largest fair in Vermont – Champlain Valley Fair – which draws in the crowds each summer. The local Champlain Valley Exposition also hosts a program of events spanning arts and entertainment, education and agriculture. Meanwhile, foodies can stock up on local Vermont produce at the weekend farmers' market. 

 

Burke, Caledonia County

The cute little town of Burke nestles beneath the 3,281-foot peak of Burke Mountain, whose vast forested slopes make it the perfect base for outdoor pursuits no matter the season. The Burke Mountain Ski Area offers snowy runs in winter, while the town is a hub for biking, hiking and swimming in the warmer months. Freshwater lakes including Lake Willoughby provide more opportunity for adventure.

Barre, Washington County

Just a short distance from Montpelier, Barre is a close-knit community deep in the Green Mountains of central Vermont. Visitors can learn about its long history at the Granite Museum that sits inside an old processing shed listed on the US National Register of Historic Places. The local granite was used by the area’s Scottish immigrants to erect a monument to famous Scottish poet Robert Burns in 1899, which still stands today in downtown Barre.

Middlebury, Addison County

This centuries-old mill town is now home to a college and a burgeoning craft brewery and distillery scene that can be sampled on the Middlebury Tasting Trail. Set on Otter Creek, Middlebury has oodles of history too, and you can soak it all up at the Henry Sheldon Museum of Vermont History or the Vermont Folklife Center. As well as a collection of gorgeous heritage buildings, the town is home to Vermont’s oldest covered wooden bridge – Pulp Mill Bridge – which dates back to 1820.

Randolph, Orange County

Full of rural charm, rambling old houses and restored farmsteads, Randolph was built on agriculture, and its curved red barns, covered wooden road bridge and old railroad station hark back to days gone by. Visitors can expect a warm welcome in the red-brick stores and eateries of downtown, where the old Chandler Music Hall features regular stage shows and the antique Playhouse Movie Theatre screens the latest films.

Stratton, Windham County

The tiny scenic town of Stratton is a mountainside snowsports hub that’s just as attractive in the summer as in winter. You'll be able to try your hand at snowboarding and skiing or take to trails wiggling through the mountains. The alpine-style village is packed with cozy lodges, plus comfort food spots like Benedicts, which dishes up hearty breakfasts.

 

Quechee, Windsor County

The idyllic riverside settlement of Quechee, part of the town of Hartford, is an arty heritage village with a 19th-century water mill, originally settled in the 1760s. It now houses a glass-blowing and pottery studio run by renowned craftsman Simon Pearce with a showroom and workshop open to visitors. Head to the main town of Hartford to explore the Main Street Museum, detailing the area’s industrial history.

Greensboro, Orleans County

A peaceful enclave in the far north of Vermont (which is dubbed the Northeast Kingdom for its natural seclusion), Greensboro borders Caspian Lake and has been an escape for countless artists and writers over the generations. Alongside cute lakeside cottages, traditional country stores and a gallery housed inside a converted mill, Greensboro hosts regular shows and events at the Highland Center for the Arts and summer productions from Mirror Theater and Circus Smirkus, which both have bases in the town.

St Johnsbury, Caledonia County

The center of the Northeast Kingdom, St Johnsbury is small and picturesque with red-brick storefronts, dreamy spires and antique turreted houses dating to the 19th century. Its maple syrup production means it's known as the Maple Center of the World, and visitors can get a taste of its heritage at Maple Grove Farms of Vermont, which also hosts a cute Maple Museum. The downtown area is lined with art galleries and boasts the interesting Fairbanks Museum, plus the state’s only public planetarium.

Wilmington, Windham County

Around a half-hour drive from Bennington in the south of the state, Wilmington is another rustic little town surrounded by forest-covered hills and mountains. An ideal stop along the scenic Route 100, Wilmington’s downtown diners, cute artisanal stores and intriguing galleries are housed in picture-perfect heritage buildings. Plus there’s a weekend flea market and hiking trails fanning out into the forest.

Waterbury, Washington County

In the heart of Vermont where several scenic roads meet, Waterbury is a sweet spot brimming with heritage and sensory delights. Stroll Waterbury Village Historic District and downtown to browse eclectic independent stores and artists' studios, or sample the local tipples at Prohibition Pig Brewery and Cold Hollow Cider Mill. Don't miss a behind-the-scenes tour at the factory of world-famous ice cream brand Ben and Jerry’s.

Rutland, Rutland County

A dinky town in central Vermont with a great arts scene, Rutland has a downtown that's splashed with colorful murals, and its mapped Sculpture Trail takes visitors around a wide array of interesting public artworks. Alongside galleries and shops selling unique gifts and one-off clothing, the town has a world-class performing arts venue – the Paramount Theatre – which dates back to 1912.

Warren, Washington County

A true Green Mountain State treasure, the tiny town of Warren sits in Mad River Valley between the two ranges of the Green Mountains, making it a natural base for winter sports and outdoor adventures (that heritage dates back to the 1930s, when the first ski lift was built). Over the years its snowy slopes have attracted big names including the Kennedys, while in summer the crystalline natural swimming hole at Warren Falls is popular. Vermont’s scenic Route 100 crosses the town, as does the Long Trail hiking path that runs to the border with Canada.

Springfield, Windsor County

Springfield is a former industrial town powered by Black River Falls, and traces of its history can still be seen in its Victorian waterside mills and old downtown area. For sheer old-world charm, don’t miss the Eureka Schoolhouse, which is the earliest surviving structure of its kind in Vermont, dating back to 1785 and sitting right next to the Baltimore Covered Bridge. You won’t find the Simpsons living in Springfield, but the town did host the world premiere of The Simpsons Movie at its little red-brick cinema in downtown.

Westminster, Windham County

Travelers tracing Vermont’s history can follow in the footsteps of the first settlers in Westminster, which is the state’s oldest town, chartered in 1735. On the border with the state of New Hampshire, the rural town was once named Township Number One and its backstory includes being the first capital of the Republic of Vermont, which was independent from 1777 until 1791 when it was incorporated into the United States.

Williston, Chittenden County

On the outskirts of Vermont’s most populated city, Burlington, is the timeless haven of Williston, which makes a great alternative base for exploring the epic landscapes of the Green Mountains. Once a collection of quaint farmsteads, Williston now has a thriving downtown, with Lake Champlain and Lake Iroquois within easy reach.

Woodstock, Windsor County

Woodstock embodies quintessential Vermont charm. Its grand old houses, white picket fences, books stores, antiques shops and wooden-roofed road bridges (such as Middle Covered Bridge) are irresistibly photogenic. It's the perfect place to step back in time and experience 19th-century New England, brought to life at Billings Farm and Museum. Make a pitstop to refuel at the Mountain Creamery, before exploring the beautiful conservation area of Marsh-Billings-Rockefeller National Historical Park.

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