The Most Beautiful Towns in Vermont, USA

Woodstock, Vermont, USA Middle Covered Bridge
Woodstock, Vermont, USA Middle Covered Bridge | © Sean Pavone / Alamy
Photo of Rachel Gould
Art & Design Editor4 May 2021

If you want your American vacation to be both quiet and crammed with history, then Vermont is the place for you. The New England state is the second-least-populous in the USA; combine that with the rural architecture and it’s a consistent throwback to settler-era tranquility.

Chester

Architectural Landmark
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USA, New England, Vermont, Chester, town view
Chester | © Hemis / Alamy Stock Photo

Chester is best known for the two historic districts, both of which are listed in the National Register of Historic Places. One of them, Stone Village, was named so because of the dominance of granite houses; the second, Chester Village, features a typically New England federal and colonial aesthetic. Chester is home to charming inns, antique shops, galleries and great restaurants. Additionally, it caters for cyclists, boaters and skiers, lying within driving distance of Okemo, Mount Snow and Killington. Stop by in September and you’ll also be able to attend the Chester Fall Festival.

Dorset

Architectural Landmark
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Dorset, Vermont, in autumn
Dorset | © Susan Pease / Alamy Stock Photo

The quiet and charming town of Dorset lies amid the hills of Bennington County in southern Vermont. Chartered in 1761, Dorset is the location of the oldest marble quarry in the country, which provided stone for the sidewalks and the marble church next to the village green, as well as the main branch of the New York Public Library. Take a swim in the quarry, partake in the Dorset Theatre Festival, and explore the historical scenery for a relaxing and restorative mini-vacation.

Grafton

Architectural Landmark
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Grafton Inn_1fcc0ed8
Grafton Inn | Courtesy of Grafton Inn / Expedia

Discover the scenic beauty and historic buildings here for a glimpse into the early colonial days. In the 1800s, Grafton was a popular stagecoach stop for those traveling to Albany, New York, through the Green Mountains. As a result, the area acquired a market for hospitality; it maintains the Grafton Inn, which dates back to 1801 and remains one of the oldest operating hotels in the United States. That’s not the only preserved building either; many of the the original architecture here has been preserved in order to keep an authentic New England atmosphere. Come by in winter to enjoy snow-covered hills and cross-country skiing.

Manchester

Natural Feature
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© Jon Arnold Images Ltd / Alamy Stock Photo

Popular among New Yorkers, New Englanders and even Europeans in recent years, Manchester is a great base for skiing and hiking in the Vermont countryside. The village has a vibrant cultural scene with shops, museums and galleries; the theaters regular show concerts and plays too. You can tour old buildings, peruse craft fairs ,and dine in one of many artisanal restaurants and cafes.

Montpelier

Architectural Landmark
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State Street in downtown, Montpelier, Vermont, USA
State Street in downtown Montpelier | © Ian Dagnall / Alamy Stock Photo

Montpelier is the smallest state capital in the United States, letting it have all the charm and character of a quiet township. Simultaneously, it also boasts a vibrant cultural scene with something for art, music, history and nature lovers alike. Visit the Vermont Historical Society Museum, the TW Wood Art Gallery and the Vermont State House for lessons in local history, or wander Hubbard Park and visit the farmers’ markets for a taste of day-to-day Montpelier life. Home of the New England Culinary Institute, Montpelier is also a great place to eat out, whether in lively restaurants or cute cafes.

Shelburne

Architectural Landmark
Map View
© Joanne Pearson / Alamy Stock Photo

Located on the shores of scenic Lake Champlain, Shelburne is a lush and affluent suburb of Burlington. In addition to a nature park and a lakeside beach there are three main attractions. Roam the 19th-century Shelburne Farms estate, complete with a 110-room summer residence, a five-story barn and a two-acre (0.8ha) courtyard with hayrides. History buffs can learn about Vermont heritage at the Shelburne Museum, where American art and an original steamboat are the draws. Lastly, who can resist the loveable Vermont Teddy Bear Factory?

Stowe

Architectural Landmark
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Main Street, Stowe, New England, Vermont, USA
Main Street, Stowe | © Peter Conner / Alamy Stock Photo

The lively town of Stowe is an ideal destination throughout the year, but attracts particularly big crowds every winter thanks to the popular Stowe Mountain Resort. In town, you can wander arts and crafts fairs, museums and galleries, attend musical and theatrical performances, and take part in seasonal activities like outdoor film festivals. Stowe is also extremely ‘grammable, thanks to the rolling green hills in summer and vibrant fall foliage of fall.

Waitsfield

Architectural Landmark
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Charming town of Waitsfield in Vermont. 2BJ4BFW
Charming town of Waitsfield in Vermont. | © Loop Images / John Greim / Alamy

Located in the heart of the Mad River Valley in Washington County, Waitsfield is a must for winter sports lovers in search of backcountry skiing. Not quite as extreme? The natural beauty surrounding Waitsfield has drawn numerous talented artists over the years, and today it’s home to a number of galleries and studios. Those who love the outdoors can visit farms, roam farmers’ markets and take guided hikes in the hills.

Weston

Architectural Landmark
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2F447TG geography / travel, USA,
Vermont, Weston, Vermont | © INTERFOTO / Alamy

The small town of Weston is home to several charming B&Bs, inns and lodges – perfect for a cozy romantic weekend or a fun family getaway. Around town, there are shops selling crafts and artisanal goods, art galleries and craft studios – all of which are still family-owned and -operated. Weston is the perfect place for a quiet change of scenery in a picturesque town with a charming and well-preserved heritage.

Woodstock

Architectural Landmark
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2D521TP - OCTOBER 9, 2020: : The Village Butcher shop storefront with morning autumn lights
The Village Butcher shop storefront with morning autumn lights, WOODSTOCK, VT, USA | © Miro Vrlik Photography / Alamy

The capital of Windsor County, Woodstock is one of the best local assets. It was settled in the mid-18th century and is considered the quintessential New England village; picture a quaint green, lined by a mix of restored Greek Revival and Georgian-style homes, all within short walking distance of old country farms. In the town center, sample maple syrups and cheeses at Sugarbush Farm, then explore the Marsh-Billings-Rockefeller National Historical Park. Go in fall to attend the Billings Farm and Museum’s annual Harvest Weekend, or simply enjoy the picturesque surroundings, beautiful all year.

These recommendations were updated on May 4, 2021 to keep your travel plans fresh.

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