12 Greatest Cities & Villages

Vermont is known far and wide for its picturesque scenery. Aptly known as the Green Mountain State, Vermont’s hallmark is the Green Mountain National Forest and there is so much to do in the foothills. Honestly, if you’ve ever been inspired to visit New England during your annual Gilmore Girls binge, Vermont will satisfy all the images you’ve conjured in your head.

Almost as sugary sweet as the famed Vermont maple syrup that travelers come to savor for themselves, the towns in this state are so charming. Vermont’s numerous hiking trails nearly outnumber the residents. Vermont has the second smallest population of all the states–to be fair, it’s one of the smallest states by size, too.

This part of New England has more to offer than just its tremendous natural beauty. Fine dining where you least expect it, quaint towns, outdoor activities galore, and a kind populace await you.

Some of the places we’ve listed are technically cities, while others could be the smallest towns you’ve ever visited. Either way, you’re bound to walk away from this vacation with a more profound sense of why Vermont is frequently called the best state to live in. Who knows, maybe you’ll end up being a Vermonter one day.

Plus, believe it or not, some of these little towns are where you’ll find some of the best hotels in Vermont! Some have indoor and outdoor pools, spas, a restaurant on site, antique furnishings with modern comforts, and even spacious suites for family affairs.

TL;DR

• Best Area for First-Timers: Burlington
• Best Area for Budget Travelers: Brattleboro
• Best Area for Luxury Travelers: Stowe
• Best Area for Arts and Culture: Montpelier
• Best Area for Families: Woodstock
• Best Area for Foodies: Waterbury
• Best Area for Skiing: Stowe

Where to Stay in Vermont

1. Montpelier

When looking for places to visit in Vermont, it makes sense to start with Montpelier, the capital. Established in the middle of the Green Mountains, this little city of just over 8,000 residents is an obvious choice to visit, especially for Vermont first-timers. It’s known as one of the best small arts towns in the country.

Dating back to the 1800s, Montpelier is full of historic goodies for visitors to enjoy. Check out the gold-domed capital building, the Vermont Historical Society Museum, and the Kent Tavern Museum. The art scene here showcases spots like Susan Calza Gallery, Katie O’Rourke Art, and the Center for Arts and Learning.

A bonus to staying in a city as petite as Montpelier is that everything is within walking distance. You can have a car, but if you’re staying in a hotel in town, you won’t really need it. Or, if you really want to see everything, why not take a day-long guided tour of the town and Mad River Valley?

Still, if you want to get out into nature a bit during your visit, you don’t have to go far. From the 200 acres of Hubbard Park along the Winooski River to hiking Camel’s Hump or meandering the Central Vermont Path, nature is always calling.

Fun Things to Do in Montpelier

• Vermont Historical Society Museum
• See the capital building
• Hubbard Park
• Central Vermont Path
• Kent Tavern Museum
• Coburn Covered Bridge

 Where to Stay in Montpelier

2. Burlington

Just south of the Canadian border, along Lake Champlain, Burlington is a much larger city than Vermont’s capital. This highly walkable city is known for its collegiate status, museums, arts scene, and plenty of shopping. The pedestrian Church Street Marketplace is a particular favorite of locals and visitors alike.

When you take to the streets of Burlington, you quickly learn that there is a lot to absorb. You may want to take a self-guided walking tour of the city early in your trip to determine best what to focus on.

You’ll be impressed to learn that the city’s footprint goes far beyond its ties to Ben & Jerry’s Ice Cream. There is even an incredible craft brewing scene here, which could pair well with the aforementioned ice cream.

This northwestern city’s museums can help you get to know the area better with the unique perspectives of the Ethan Allen Homestead Museum and Historic Site or the Shelburne Museum. The former showcases the life of the famed Revolutionary War hero, while the latter curates American folk and decorative art in historic buildings.

Visiting Burlington also offers the chance to stay at a local hotel rather than a chain you’re familiar with. The Green Mountain Suites Hotel, an all-suites accommodation, is worth considering. Green Mountain Suites Hotel has affordable prices with complimentary breakfast and a nightly wine/beer reception with snacks.

Fun Things to Do in Burlington

• Church Street Marketplace
• Visit Lake Champlain
• Shelburne Museum
• Ethan Allen Homestead Museum
• Burlington Farmers Market
• Fleming Museum of Art

 Where to Stay in Burlington

3. Brattleboro

Known initially as Brattleborough, Brattleboro is a small city in Southern Vermont near the New Hampshire border. This ultra-artsy city is in the foothills of the Green Mountains, with the culture of a significant metropolitan area mixed with the vibes of a small, charming town. If you’re a culture vulture wondering where to stay in Vermont, look no further.

In that vein, you can’t turn a corner without encountering art in Brattleboro. From a visit to the Brattleboro Museum & Art Center, shopping at Vermont Artisan Designs or Fine Arts Vermont, and watching agape at Randi Solin Glass, you’ve got a full itinerary.

Shoppers will absolutely adore Brattleboro for its community of boutiques. This city is chock full of vibrant, local businesses to explore along the banks of the Connecticut River. Once shopping is done for the day, or you need a little break, you can pop over to Hermit Thrush Brewery or Saxtons Distillery for a quick drink.

Should you need to get out of the city altogether, head over to Fort Dummer State Park, which is just outside of Brattleboro. If you’re visiting Vermont in the autumn, you need to check out the gorgeous fall foliage at Fort Dummer. Fort Dummer was founded in 1724 and was the first European settlement in Vermont.

Things to Do in Brattleboro

• Creamery Covered Bridge
• Brattleboro Museum & Art Center
• Estey Organ Museum
• Saxtons Distillery
• Hermit Thrush Brewery
• Fort Dummer State Park

 Where to Stay in Brattleboro

4. Woodstock

No, not that Woodstock in New York, where the famed music festival took place near. Woodstock Vermont is often called the prettiest town in the country, and it’s easy to see why.

Its natural beauty abounds in the quaint town with lots of farm-fresh dining, hiking trails, and hospitality right in the state’s center. Don’t let Woodstock’s size let you believe that it doesn’t have a lot to offer.

Given its small stature, much of what you’ll find here to do takes place in nature. From exploring the Ottauquechee River to walking trails up to Mount Tom, outdoorsy folks will be right at home here.

Outdoor activities are abundant in or around Woodstock, with difficulty levels ranging from easy to challenging. It’s ideal for all abilities.

Be sure to leave time to visit Marsh-Billings-Rockefeller National Historical Park, though. This is the only national park dedicated entirely to the history of nature conservation in the United States.

It’s named for environmentalist George Perkins Marsh, conservator Frederick Billings, Billings’ granddaughter Mary French Rockefeller, and her husband Laurance S. Rockefeller, the famed conservationist.

Woodstock is also where you’ll find two of the best hotels in Vermont: the Woodstock Inn & Resort and the 506 on The River Inn. Both hotels are perfect for a romantic getaway, especially Woodstock Inn, which has an incredible spa.

Things to Do in Woodstock

• Marsh-Billings-Rockefeller National Historical Park
• Hike Mount Tom
• Ottauquechee River
• Taftsville Covered Bridge
• Sugarbush Farm
• Collective the Art of Craft
• Woodstock Farmers Market

 Where to Stay in Woodstock

5. Manchester

Located in the heart of the Green Mountains, Manchester is a former iron mining town. Now, this Vermont treasurer has the aesthetic you’d expect of a quintessential New England town surrounded by the nature of the Green Mountain National Forest. Adventurers may even want to hike their way up Mount Equinox.

Manchester may be most famous for being home to Hildene, the sprawling Georgian Revival mansion that belonged to Robert Lincoln. Robert, Abraham Lincoln’s only child to survive to adulthood, and his wife Mary had the mansion built in 1905. Lincoln’s descendants lived in the home until 1975. Now, it serves as a museum to the Lincolns and the Pullman company, which Robert ran for a time.

In another part of the museum world, Manchester also houses the American Museum of Fly Fishing and the Southern Vermont Arts Center. Since Manchester has become such a destination town, there are also fine dining options and plentiful shopping opportunities as well. You could even visit the North Meadow Farm for some hands-on cow time.

Linksmen will love the golf course at the Equinox Golf Resort. Named for the nearby mountain, Equinox is one of the best golf resorts in the country. Another option, the Reluctant Panther Inn, with its fun name, is one of the best hotels in Vermont – especially if you’re looking for a luxury boutique experience.

Things to Do in Manchester

• Visit Hildene
• Hike Mount Equinox
• Play a round at the golf course at Equinox Golf Resort
• American Museum of Fly Fishing
• Southern Vermont Arts Center
• Visit Reluctant Panther Inn
• North Meadow Farm

 Where to Stay in Manchester

6. Stowe

Watched over by Mount Mansfield, Stowe is the smallest Vermont town we’ve mentioned so far. Also known as the Ski Capital of the East, the country’s oldest ski patrol is found here, and it was also the birthplace of Alpine skiing in Vermont.

It’s hard to ignore Stowe’s ski ties since the looming Mount Mansfield is the state’s highest peak. Checking out the mountain is easily done from Smugglers’ Notch State Park – you can even camp here if you want to!

When you can pull yourself away from the slopes, you can continue the theme in Stowe. Here, you’ll find the Vermont Ski and Snowboard Museum for all the winter sports history you could want. Temporary exhibits roll in and out of the museum, though their collection of sports equipment, photos, and other adjacent paraphernalia are always there to see.

The brewing scene in Stowe is also worth noting. Stop by the range of local breweries like The Alchemist Brewery, Stowe Cider, or Idletyme Brewing Company for a warm-up. Explore these spots on your own or enjoy a half-day guided brewery tour.

Don’t forget to visit two of Stowe’s adorable accommodations, even if you don’t stay there, too: The Little River Inn and the Austrian-inspired Trapp Family Lodge. If the Trapp name sounds familiar, that’s because it is! It’s owned and operated by the von Trapp family, who were the inspiration behind the von Trapps in The Sound of Music.

Things to Do in Stowe

• See the Trapp Family Lodge
• Vermont Ski and Snowboard Museum
• Alchemist Brewery
• Mount Mansfield
• Goldbrook Covered Bridge
• Bingham Falls

 Where to Stay in Stowe

7. Bennington

Vermont’s first town, founded in 1749, Bennington borders both New York and Massachusetts in the southwestern corner of the state. Because of its storied past, the town has a lot of historical places to visit. It is also where the Bennington Triangle nickname came from when many people went mysteriously missing in the area from the 1920s to 1950s.

To the delight of architecture fans everywhere, Bennington is also home to several covered bridges. These iconic structures, especially when placed against stunning fall foliage, are easy to access and even easier to appreciate. Here, you can see the Henry Covered Bridge, the Silk Road Covered Bridge, the Chiselville Covered Bridge, and the Paper Mill Village Bridge.

If you want to get to know the state and area a bit better, visit the Bennington Museum. With artifacts dating back to the mid-1800s, this museum encompasses the town’s history and art. There are 13 galleries in the museum with permanent collections as well as visiting exhibitions. Some permanent exhibits include Gilded Age Vermont, Grandma Moses, and Across the Street: Historic Bennington.

You also absolutely need to see the incredible Park-McCullough Historic Governor’s Mansion, which is one of the best-preserved Victorian mansions in all of New England. This 35-room grand mansion was built in the Second Empire Style with some elements of Romantic Revival style as well.

Things to Do in Bennington

• Park-McCullough Historic Governor’s Mansion
• Bennington Museum
• Covered bridge visits
• The Dollhouse and Toy Museum of Vermont
• Molly Stark Trail

 Where to Stay in Bennington

See Related: A Route 100 Vermont Road Trip Itinerary You’ll Want to Copy

8. Middlebury

Founded in 1761, the town of Middlebury is a beautiful New England town. Home to Middlebury College, it is awash in activity even when school is out for the year. In fact, Middlebury College is considered a Little Ivy or a smaller school that can compete with the big Ivy League institutions.

Unlike the covered bridges of Bennington, the bridges in Middlebury aren’t as aesthetically vibrant. Even so, the Halpin Covered Bridge and Pulp Mill Covered Bridge are still worth seeing. These wooden bridges don’t have the trappings of other New England-covered bridges, yet they still carry the unique style that made these structures so fascinating to visitors.

Middlebury isn’t the oldest town in Vermont, yet the Henry Sheldon Museum demonstrates much of the state’s history. Started in 1884, it is the country’s oldest community-based museum. In addition to the temporary exhibits, the museum holds a permanent collection of 19th and 20th-century Vermont artifacts and art.

For more art, head over to the Middlebury College Museum of Art. This college museum holds both Asian, European, and American art ranging from 4000 BC to the present day. Some of the collection highlights include House of Fabregé, Kongo-Vili Power Figure, and Shahzia Sikander’s The Perennial Gaze Takes Pride of Place.

Things to Do in Middlebury

• Middlebury College Museum of Art
• Halpin Covered Bridge and Pulp Mill Covered Bridge
• Henry Sheldon Museum
• Town Hall Theater
• Lincoln Peak Vineyard
• Appalachian Gap Distillery

 Where to Stay in Middlebury

9. Waterford

A neighbor to Concord, Waterford was established in 1870 as Littleton. Though small, Waterford is a visitor’s haven for getting out of the hustle and bustle of city life. It has several hotels, restaurants, attractions, and even a dog chapel.

That’s right, there’s a dog chapel in Waterford. Dog Mountain’s Dog Chapel was founded in 2000 by artist Stephen Huneck to represent peace, love, and remembrance.

Since its creation, visitors have helped transform the space with notes, photos, and art. These little tokens can be left to spread the memory left behind on the chapel walls.

Just outside of Waterford in St. Johnsbury, the Fairbanks Museum & Planetarium is an amalgamation of natural science museum, planetarium, and history museum.

The museum’s personal collection includes 30,000 objects. Permanent exhibits demonstrate various elements of natural history and space, while temporary exhibits like Dinosaurs Among Us keep the museum fresh for repeat visitors

You should also consider a visit to the award-winning Rabbit Hill Inn. This historic inn is one of the best hotels in Vermont.

A luxury bed and breakfast experience, this hotel is best for couples since there are dress-for-dinner attire requirements. Plus, since the hotel doesn’t have televisions, it’s a great excuse to relax and unwind.

Things to Do in Waterford

• Dog Mountain Dog Chapel
• Fairbanks Museum & Planetarium
• St. Johnsbury Athenaeum
• Northeast Kingdom Artisans Guild
• St Johnsbury History & Heritage Center

 Where to Stay in Waterford

See Related: Things to Do in Massachusetts & Places to Visit

10. Grafton

Grafton is where you go if you need a Vermont-style vacation without the crowds or overly planned itineraries. This tiny town doesn’t have much stuff; instead, it is a place for disconnection and slow living. For fall foliage lovers, head to Grafton for all the autumnal colors you could want without crowded roads of visitors doing the same thing.

When you want to escape nature, you don’t have to go far to still enjoy what nature entails. At the Nature Museum, you can learn more about the natural world and how to protect it.

Or, if you visit in September, perhaps you can even pay a visit to the museum’s annual Fairy House Festival. The museum itself is open on weekends (and Fridays); however, the Magic Forest Playscape and Chapman Meadow areas are open every day from dawn until dusk.

Outdoorsy travelers will love the easy access to Jamaica State Park from Grafton. This park, with over 700 acres, is perfect for all kinds of recreational activities like cross-country skiing, mountain biking, hiking, and swimming. Jamaica State Park is also where you’ll find the Hamilton Falls Natural Area, which includes a six-mile out-and-back hike to the waterfall.

If you haven’t had maple syrup in Vermont, you can also visit Plummer’s Sugar House in Grafton. This working sugar house produces all kinds of maple syrup and other maple products. They offer a free facility tour with a purchase from their shop.

Things to Do in Grafton

• Nature Museum
• Jamaica State Park
• Plummer’s Sugar House
• Grafton Trails & Outdoor Center
• Bellows Falls Opera House
• Grafton Historical Society

 Where to Stay in the Grafton area

See Related: Best Things to Do in Boston, Massachusetts

11. Chittenden

Nestled between Lake Champlain and the Green Mountains, Chittenden is a natural haven for travelers in Vermont. While being part of the Crossroads of Vermont is a feat in and of itself, Chittenden’s main draw is its vast natural resources.

Whether you’re visiting for mountain biking or downhill skiing, there’s always something to enjoy. It’s also an easy visit from nearby cozy lodgings at Mountain Meadows Lodge or Mountain Top Inn. The latter, in Chittenden, is our pick or best overall accommodation in Vermont. This luxe Inn has a heated outdoor pool, outdoor hot tub, fitness center, and spacious guest rooms.

A short drive away in Proctor, the Vermont Marble Museum introduces visitors to the state’s rich history of geological discovery. There are 16 galleries in the museum devoted to demonstrating how marble has been used throughout the country and the world. Some of the exhibits include The Tomb of the Unknown Soldier, the Geological/Historical Display, the Marble Chapel, and the Hall of Presidents.

Also, in the nearby town of Proctor, the only actual castle in Vermont resides. The Wilson Castle, built in 1885, is a unique building because it combines several architectural styles, including Queen Anne and Romanesque Revival.

Several different owners lived in the castle until the 1950s. By 1962, it opened for public tours.

If you’re up for an hour’s drive out of town to see an incredible work of art, head up to Randolph to see the Whale’s Dance. Actually named Reverence, the sculpture was created in 1989 out of 36 tons of African black granite. This incredible work of art is meant to reflect the planet’s fragility.

Things to Do in Chittenden

• Gifford Woods State Park
• Vermont Marble Museum
• Wilson Castle
• Chittenden Reservoir

 Where to Stay in the Chittenden area

See Related: 2 Days in Boston: A Complete Itinerary to See Everything

12. Shelburne

Another town along the shores of Lake Champlain, Shelburn, is probably best known as the home to the Vermont Teddy Bear Factory and Shelburne Farms. Just a few miles away from Burlington, this town is a lovely day trip to add to your itinerary or a place to stay if you’d rather avoid a larger city. Shelburne has plenty to keep you busy with a small town fell to boot.

Shelburne’s cuddliest stop is definitely the beloved Vermont Teddy Bear Factory. Established in 1981, the factory has since become the largest handcrafting teddy bear factory in the United States.

They sell more teddies than most manufacturers worldwide, and their bears are too cute to miss. Take a tour of the factory and even stop by the Make a Friend for Life station to assemble your own Vermont teddy.

The town’s other most notable location is Shelburne Farms. This is a working farm that also runs as a non-profit sustainability education center.

Depending on the time of year you visit, there are different activities you can participate in or watch at the farm. In addition to learning about things like cheesemaking, you can also explore the historic manor house and five onsite cottages. You can even stay here!

If you stay downtown, you are within walking distance of Shelburne’s adorable shops and restaurants. When it comes to things to keep you busy, there is far more than just teddies and farms. You can indulge in local history at the Shelburne Museum, go antiquing, relax at the Shelburne Vineyard, or live your autumnal fantasies at Shelburne Orchards.

Things to Do in Shelburne

• Vermont Teddy Bear Factory
• Shelburne Farms
• Fiddlehead Brewing Company
• Shelburne Orchards
• Wild Hart Distillery
• Shelburne Museum

 Where to Stay in Shelburne

See Related: Best Hikes in New Hampshire to Try This Year

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Amanda is a Chicago-based queer travel, arts, and lifestyle writer who is passionate about exploring the world. Her work has been featured in Newcity Stage, The Chicago Reader, Huffington Post, and Yahoo, as well as the November 2022 book, “Chicago Like a Local” and other travel journals available on Amazon. Amanda’s favorite destinations include Costa Rica, Prague, Dublin, Hong Kong, and every Disney park she’s visited.