Vermont is one of New England's most stunning states, worth visiting year-round for its diverse attractions and activities. Autumn is the perfect time to enjoy Vermont’s fall foliage on a mountain train ride, while in winter, tourists take scenic winter drives that showcase spectacular snow-covered landscapes. Pro-tip, though, when figuring out how to plan a budget-friendly ski trip to Vermont, look into season passes and off-season ticket deals.

Aside from its exciting year-round activities, Vermont has beautiful towns that are worth visiting any time of the year. From charming, historical towns to mountain towns, there are plenty of options to choose from when deciding which are the best towns to visit in Vermont. But here are the top recommendations.

UPDATE: 2023/10/19 16:18 EST BY ALICIA REMMY

Two More Of The Best Towns In Vermont Tourists Should Visit

Travelers looking for the prettiest towns in Vermont can never go wrong with these 16 picks. This list has been updated to give tourists more of the most beautiful towns in Vermont to help them get the most out of the Green Mountain State. Each town also has an added section of the top attractions to visit for relaxing or thrilling outdoor adventures.

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16 Bennington

Battle Memorial, Bennington
Eixo, Public domain, via Wikimedia Commons
Battle Memorial, Bennington, Vermont, USA

Bennington is one of the most beautiful snow-covered towns in Vermont. Tourists should visit in winter. But aside from its winter charm, there's a lot to keep travelers glued for days any time of the year. They enjoy exploring downtown, visiting historical attractions such as the Bennington Battle Monument and the Bennington Museum, and trying farm-to-table dishes for unique dining experiences.

The Apple Barn is one of New England's best little country bakeries, famous for its apple cider donuts and other signature flavors. Outdoor enthusiasts also find their fill hiking nearby hiking trails that lead them to breathtaking vistas and nature parks.

  • Best places to visit in Bennington: Bennington Battle Monument, Bennington Museum, Old First Church, Park-McCullough Historic House, Bennington Center for the Arts

Apple Barn Country Bake Shop

  • Address: 604 US Route 7 S, Bennington, VT 05201
  • Hours: Daily, 8:30 am to 4:00 pm

15 Weston

A view of a field starting to change into fall colors in Weston, Vermont
Photo by Austin Curtis on Unsplash
A view of a field starting to change into fall colors in Weston, Vermont 

Steeped in history and old-world charm, Weston is one of the most beautiful towns in Vermont worth visiting to enjoy the slow pace of life. Located in Windsor County, this charming town allows tourists to lose themselves in its quaintness while strolling along the streets with New England-style architecture and other sites dating back to the 80s.

The rolling hills of the breathtaking Green Mountains in Weston are the perfect places for outdoorsy people to hike, leaf peep, and ski, depending on the season. However, those interested in learning about the town’s history and what it was like in the 18th and 19th centuries head to The Old Mill Museum.

  • Best places to visit in Weston: The Vermont Country Store Weston, The Old Mill Museum, Farrar-Mansur House, The Weston Village Store

Weston Theater Company

14 Shelburne

Webb Gallery, Shelburne
John PhelanCC BY-SA 3.0, via Wikimedia Commons
Webb Gallery, Shelburne,Vermont, USA

Shelburne is one of the most popular, prettiest towns in Vermont for a reason. It has plenty of fun activities for people of all ages, such as those at Shelburne Farms. They offer a wide variety of delectable local maple syrup and Vermont cheeses, as well as a variety of fun activities, tours, and workshops.

Another interesting place to visit in town is the Shelburne Museum, founded in the middle of the twentieth century and has exhibits on art and design spread across 39 different structures. The town also has charming shops, art galleries, and restaurants, celebrating Vermont's rich heritage and regional cuisine.

  • Best places to visit in Shelburne: Shelburne Museum, Shelburne Farms, Shelburne Orchards, Fiddlehead Brewing Company, Shelburne Vineyard

Shelburne Museum

  • Address: 6000 Shelburne Road, Shelburne, VT 05482
  • Hours: Daily, 10:00 am to 5:00 pm (May 13 through October 22)

Shelburne Farms

  • Address: 1611 Harbor Road Shelburne, Vermont 05482
  • Hours: Daily, 10:00 am to 5:30 pm (May 13 through October 22)

13 Brattleboro

Main Street, Brattleboro, Vermont

John PhelanCC BY-SA 4.0, via Wikimedia Commons
Main Street, Brattleboro, Vermont, USA

Brattleboro, Vermont, offers a wealth of attractions for a trip that is both exciting and relaxing, including a charming downtown, fascinating museums, galleries, and restaurants, as well as fun festivals, including the annual Brattleboro. Its picturesque setting, surrounded by majestic mountains, dense forests, and a serene river, makes it a perfect place for a nature retreat.

The quaint downtown area, with its stores, galleries, and farm-to-table restaurants, offers lovely experiences. The Creamery Covered Bridge is another top-rated attraction in Vermont that draws tourists with its historic charm and attractive backdrop for photo opportunities.

  • Best places to visit in Brattleboro: Brattleboro Museum & Art Center, Fort Dummer State Park, Madame Sherri Forest, Brattleboro Farmers' Market, Creamery Covered Bridge, Molly Stark State Park

Creamery Covered Bridge

  • Address: Guilford Street Off Route 9 West, Over Whetstone Brook, Brattleboro, VT 05301

12 Williston

Old Brick Tavern, Williston
Doug Kerr from Albany, NY, United StatesCC BY-SA 2.0, via Wikimedia Commons
Old Brick Tavern, Williston, Vermont, USA

Williston, Vermont, near Lake Champlain, is a haven for outdoor enthusiasts and thrill seekers with opportunities like hiking, biking, fishing, kayaking, and boating amid picturesque landscapes. Furthermore, the town is home to many parks and natural areas, including the Green Mountains, which provide peaceful settings for exploration and relaxation.

Williston's bustling downtown area also has numerous independently owned stores, eateries, and breweries, providing a taste of Vermont's distinct culture. Locals love The Green Meadows Grill for its delectable staples, like hotdogs, burgers, sandwiches, and Philly Cheesesteaks.

  • Best places to visit in Williston: Catamount Outdoor Family Center, Lake Iroquois Recreation Area, Vermont National Country Club, Green Mountain Audubon Center, Williston Village Farmers Market, Brownell Mountain Trails

The Green Meadows Grill

  • Address: 2738 N Williston Rd, Williston, VT 05495-8823, United St, Williston, VT 05495
  • Hours: Tuesday, Wednesday, Friday: 11:00 am to 3:00 pm; Thursdays: 11:00 am to 7:00 pm

11 Lincoln

Lincoln, Vermont
Doug Kerr from Albany, NY, United StatesCC BY-SA 2.0, via Wikimedia Commons
Burnham Hall, Lincoln, Vermont, USA

One of the best towns in Vermont to visit is the rural town of Lincoln. Lincoln’s history dates back to 1780, when the town was chartered by the Vermont Legislature. Lincoln is the perfect getaway for travelers desiring a laid-back vacation in a farm country. The town sits at the foot of Mount Abraham and near New Haven River, offering up some breathtaking landscapes. The Old Hotel, Lincoln’s historic 1840s hotel, is a great spot to stay. Guests comment on this B&B’s kind staff, cozy rooms, and delicious breakfast.

  • Best places to visit in Lincoln: The Lincoln General Store, Lincoln Gap Road, The Old Hotel, Sunset Ledge Trail Head

Old Hotel

  • Address: 233 E River Rd, Lincoln, VT 05443
  • Amenities: Wi-Fi, free parking, free breakfast, self-serve laundry, air-conditioning
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10 Waitsfield

Waitsfield, Vermont, USA
miketnortonCC BY 2.0, via Wikimedia Commons
Waitsfield, Vermont, USA

Vermont is the perfect winter state due to its beautiful snow-covered towns, including the town of Waitsfield. During the summer months, the small town streets are lined with bright green trees, while the winter landscape includes snowy mountains and icicles. Travelers enjoy visiting Waitsfield in winter, thanks to the beautiful Mad River River Valley. This charming ski resort features a variety of trails for beginners and experts. Add to this charming lodging option for the ultimate vacation.

  • Best places to visit in Waitsfield: Mad River Ski Area, The Big Picture Theater & Café, Ben & Jerry's, Lawson’s Finest Liquids

Mad River Glen Cooperative

  • Address: 57 Schuss Pass, Waitsfield, VT 05673, United States
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9 Dorset

A historic building in Dorset Village, Vermont, USA
Doug Kerr from Albany, NY, United StatesCC BY-SA 2.0, via Wikimedia Commons
A historic building in Dorset Village, Vermont, USA

One of ten small towns in Vermont, perfect for a weekend trip, is Dorset. Dorset is home to the oldest marble quarry in the United States, established in 1785. Located right off Highway 30, this attraction includes marble stones, small cliffs, and a swimming hole and was a must-visit stop in Dorset, but now it is closed for tourists.

Travelers enjoy jumping into the waters below and going for a dip on hot summer days. The rest of the town is beautiful as well, featuring hiking trails, biking trails, mountain streams, and local markets.

  • Best places to visit in Dorset: Dorset Playhouse & Theater Festival, Emerald Lake State Park, Bromley Mountain, Green Mountains, Dorset Farmers Market, Barrows House

Emerald Lake State Park

  • Address: 65 Emerald Lake Lane, East Dorset, VT 05253
  • Hours: 10 am - official sunset

8 Grafton

Grafton, Vermont

Doug Kerr from Albany, NY, United StatesCC BY-SA 2.0, via Wikimedia Commons
Town Hall, Grafton, Vermont, USA

Located in the pretty area of Southern Vermont, this New England town is known for its rows of historic buildings and beautiful mountain views. It's one of the small Vermont towns tourists should visit in the fall for many exciting outdoor activities that showcase stunning fall foliage. Travelers interested in history will enjoy visiting the Grafton Historical Society Museum, a museum that shares Grafton’s history with visitors. The museum includes documents and artifacts from Grafton’s early manufacturing and farming days, as well as diaries from Civil War times and dioramas of the town.

  • Best places to visit in Grafton: Grafton Village Cheese Company, Grafton Trails & Outdoor Center, and The Nature Museum at Grafton

Grafton Historical Society Museum

  • Address: 147 Main St, Grafton, VT 05146
  • Hours: Tuesday 2-4 pm, Sunday 2-4 pm

7 Waterbury

Downtown Waterbury

Thomsonmg2000, CC0, via Wikimedia Commons
Downtown Waterbury, Vermont, USA

The cool Vermont town of Waterbury is a must-visit spot for foodies. Waterbury is known for its superb farm-to-table restaurants, as well as its craft breweries. Stop by Cold Hollow Cider Mill for the best cider and fresh baked goods. Cold Hollow’s hard cider is delicious, as well as freshly made cider donuts. Guests craving a heartier meal will enjoy the mill’s sandwiches and cheddar cheese biscuits.

  • Best places to visit in Waterbury: The Prohibition Pig Restaurant, Camels Hump State Park, The Ben & Jerry’s Factory, Cold Hollow Cider Mill

Cold Hollow Cider Mill

  • Address: 3600 Waterbury-Stowe Rd, Waterbury Center, VT 05677
  • Hours: 8 am-6 pm daily

6 Killington

A view of the Killington Ski Mountain, a winter paradise in the beautiful town of Killington, Vermont
Photo by Ray Esteves via Shutterstock
A view of the Killington Ski Mountain, a winter paradise in the beautiful town of Killington, Vermont

Killington is one of the prettiest towns in Vermont, luring adventurers with exciting outdoor adventures year-round. But during winter, tourists access the largest ski resort in the Eastern United States, Killington Ski Resort, with 22 ski lifts and 155 trails extending across several interconnected mountains. Nicknamed the “Beast of the East,” this winter haven has the best skiing and boarding conditions, where thrill seekers take private or group lessons to satisfy their thrill. Once the snow melts, travelers can mountain bike, hike, and rock climb in the summer or leaf peep in Gifford Woods State Park.

  • Places to visit in Killington: Gifford Woods State Park, Killington Ski Resort, Killington Distillery, Greenbrier Gift Shop, Mad Hatter's Scoops

Gifford Woods State Park

  • Address: 34 Gifford Woods Acc, Killington, VT 05751, United States
  • Hours: 10 am - Sunset

5 Woodstock

Fall foliage in a farm in Woodstock, Vermont, USA
Photo by Patrick Bald on Unsplash
Fall foliage in a farm in Woodstock, Vermont, USA

Another one of the most beautiful towns in Vermont is Woodstock. Many travelers enjoy exploring Woodstock in the fall months, as it is one of Vermont’s best towns to celebrate the fall season in. The town is surrounded by bright red, orange, and yellow trees, and Woodstock’s nature trails are breathtaking in the fall months. Popular outdoor activities in the area include hiking, running, golfing, biking, horseback riding, fishing, swimming, and paddleboarding.

Guests in Woodstock seeking the traditional farm life experience will enjoy a day at Billings Farm & Museum. This museum offers exhibits, hands-on activities like milking a cow, and the ability to meet farm animals.

  • Best places to visit in Woodstock: Taftsville Covered Bridge, Billings Farm & Museum, Marsh-Billings-Rockefeller National Historical Park, Sugarbush Farm, Woodstock Town Hall Theatre

Billings Farm & Museum

  • Address: 69 Old River Rd, Woodstock, VT 05091
  • Hours: Saturday-Sunday, 10 am-4 pm

4 Stowe

Stowe, Vermont

Photo by Triyansh Gill on Unsplash
Stowe, Vermont, USA

Skiers and snowboarders should visit Stowe, one of Vermont’s charming small towns. When planning the ultimate trip to Stowe, Vermont’s ski town, travelers should learn the best ways to get around the town and the best spots to stay. There are lovely tiny home rentals throughout Vermont, including the cozy Stowe Waterfalls Cottage. The cottage includes a kitchenette, queen bed, and outdoor fire pit.

The must-visit ski area in town is Stowe Mountain Resort. The resort features ski lifts, ski and snowboarding lessons, lodging, and equipment rentals. Athletes who enjoy freestyle terrain skiing will love the resort’s freestyle terrain park, featuring jumps, ramps, boxes, quarter pipes, and more.

  • Best places to visit in Stowe: Stowe Mountain Resort, The Alchemist Brewery, Mount Mansfield, Smugglers Notch State Park, Moss Glen Falls

Stowe Mountain Resort

  • Address: 5781 Mountain Rd, Stowe, VT 05672
  • Hours: 9:30 am-4:30 pm daily
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3 Montpelier

Main Street, Montpelier
FarragutfulCC BY-SA 4.0, via Wikimedia Commons
Main Street, Montpelier, Vermont, USA

One of the prettiest areas of Vermont is Montpelier and the surrounding area. Montpelier prides itself on offering the perfect balance of small-town charm and big-city life. This town, which is also Vermont’s capital, features a mix of historic buildings, government buildings, local storefronts, and restaurants.

Located in a valley by the Green Mountains, Montpelier offers stellar nature views. During the winter months, guests enjoy sledding through the valley and admiring the snowy scenery. Other outdoor adventures include hiking at Hubbard Park and North Branch Park and kayaking the Winooski River.

  • Places to visit in Montpelier: Vermont State House, Hubbard Park, Vermont Historical Society Museum, North Branch Vineyards, Bragg Farm Sugar House, Montpelier Mud

Hubbard Park

  • Address: 400 Parkway St, Montpelier, VT 05602, United States
  • Hours: 7:00 am to 9:00 pm

2 Chester

Chester Downtown, Vermont
Kenneth C. ZirkelCC BY-SA 4.0, via Wikimedia Commons
Chester Downtown, Vermont, USA

Chester, Vermont, is known for its charming Chester Village Historic District. Listed on the National Register of Historic Places, this section of town features wood-frame buildings, mid-1800s buildings, and several shops.

Visitors enjoy the slow-paced vibe of this town, spending leisurely afternoons strolling the town’s streets. There are plenty of antique shops, art galleries, and restaurants to try in Chester. The town’s website lists a series of events, including Chester Rod & Gun Club and Bingo, held Thursdays from 6:30 pm to 7:30 pm.

  • Best places to visit in Chester: Chester Village Green, Stone House Antique Center, DaVallia Gallery & Boutique, Magic Mountain Ski Area

Chester Rod & Gun Club

  • Address: 4137 VT Route 11 West in Chester, Vermont
  • Hours: Sundays, 10 am - 1 pm

Bingo

  • Address: Grand Hall, near VT Route 103 North, Vermont
  • Hours: Thursdays, 6:30 pm – 7:30 pm
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1 Manchester

Hildene, Manchester
Rolf MüllerCC BY-SA 3.0, via Wikimedia Commons
Hildene, Manchester, Vermont,USA

A Southern Vermont town worth visiting is the beautiful Manchester. There are plenty of fun and unique attractions in this town, including The American Museum of Fly Fishing and Seven Springs Garden & Sculpture Park.

While visiting Manchester, guests should explore Hildene, The Lincoln Family Home, formerly owned by Robert Lincoln. Guided tours are available for an extra fee for guests wishing to brush up on their history and learn about this historic site. Other visitors enjoy exploring the outdoor gardens and trails.

  • Best places to visit in Manchester: Hildene, The Lincoln Family Home- Welcome Center, Southern Vermont Arts Center, The Golf Club at The Equinox

Hildene

  • Address: 1005 Hildene Rd, Manchester, VT 05255
  • Hours: Thursday-Monday 10 am-4:30 pm, closed Tuesday-Wednesday