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Vermont Winter Getaways for an Enchanting Weekend

Is there anything as magical as a snowy winter in Vermont?

The days may be short and the roads icy, but if anyplace can embrace winter in all its glory, it’s definitely the Green Mountain State, which becomes a winter wonderland between January and March, with cold and snow stretching far beyond that.

Winter in Vermont is magical!

You may think that Vermont weekend getaways are only for skiers. Not true! While the mountains of Vermont have been attracting downhill skiers for decades, there is so much more to winter in Vermont than skiing.

The truth is, no matter where you stay in Vermont, you’re not very far from a world-class ski resort, so this post is going to focus on winter destinations in Vermont that have more to offer than just skiing.

If you’re on the fence about visiting Vermont in the winter, let me help you change your mind. Here are a few of our favorite Vermont winter getaways for the perfect snowy weekend.

Bennington and Manchester, Vermont

A snowy scene featuring Main Street in Bennington, Vermont.
Main Street in Bennington on a snowy winter day.

Bennington County in Vermont has two shire towns – Bennington in the southern part of the county and Manchester, about 30 minutes north. Between the two towns, there is no shortage of things to do in the winter, whether you’re into outdoor recreation, shopping, or cultural and historical attractions.

Where to Stay in Bennington, Vermont

We recommend spending a night in Bennington and a night in Manchester so you can explore both towns properly. In Bennington, stay at South Shire, the ‘Little Hotel’ with its beautiful Gilded Age decor on an intimate scale. South Shire houses the new Niramit cuisine of Siam, which features upscale, unadulterated Thai food.

For a more budget-friendly option, check out The Hardwood Hill, which features eclectic local artwork in every room.

The Best Hotels in Manchester, Vermont

Check out these beautiful spots for the second night of your Vermont winter getaway:

  • Inn at Ormsby Hill: For incredible luxury and attention to detail, you really can’t beat this gorgeous historic inn. Bedrooms all have luxurious jacuzzi tubs, fireplaces, and high-end linens and decor.
  • Toll Road Inn: I’ll call this a retro motor lodge. It’s tastefully designed and decorated and just down the mountain from Bromley Mountain. Oh, and it’s got a year-round hot tub for enjoying star-filled winter nights.
  • The Kimpton Taconic: We don’t often recommend chain hotels on these pages, but we always recommend the Kimpton Taconic, which is beautifully decorated, within walking distance to many shops and restaurants, and it’s dog-friendly!

What to do in Bennington and Manchester in the Winter

You’ll want to spend some time wandering around historic Old Bennington, which is just west of downtown Bennington.

Check out the Bennington Monument at the top of Monument Avenue and then stroll past 18th-century homes as you make your way to the Old First Church. You can also visit Robert Frost’s grave, which is located in the cemetery behind the church.

The Burt Henry Covered Bridge in Bennington, Vermont during a snowstorm.
The Burt Henry Covered Bridge

Since you’ll be driving north to Manchester anyway, be sure to embark on a covered bridge tour of Bennington County, which is fun no matter what time of year you visit.

In Manchester, be sure to visit Hildene, the former home of Robert Todd Lincoln (son of President Lincoln). This historic home was built in 1905 as a summer estate. Guided tours are offered throughout the year.

If you can’t imagine visiting Vermont without skiing, head east to Bromley Mountain for a day on the slopes. Bromely is a wonderful family-friendly mountain with trails for all levels of experience.

For a more mellow outdoor experience, rent snowshoes at the Mountain Goat and head to Equinox Preserve for a quiet woodland walk.

If this sounds like the perfect collection of things to do in Vermont in the winter, be sure to check out the complete winter itinerary for exploring Bennington and Manchester.

Woodstock, Vermont

A covered bridge in downtown Woodstock, Vermont, one of the best Vermont winter getaways.
Middle Covered Bridge in Woodstock, Vermont.

Woodstock is another town that fully embraces winter. While Woodstock is a popular Vermont destination year-round, winter is probably our favorite time to explore the area without the insane crowds that flock here in the summer and fall.

Woodstock was first settled in 1768, and the town has managed to preserve the historic nature of the downtown area. In fact, the entire downtown district is listed on the National Register of Historic Places. Early 19th-century homes and many Federal and Greek Revival buildings line Elm Street.

Where to Stay for your Vermont Winter Weekend in Woodstock

If you don’t mind putting a bit of a dent in your wallet, nothing compares to a weekend at the Woodstock Inn and Resort. Not only is this posh hotel located right downtown, but it also features four unique restaurants, a contemporary spa, and a Nordic Ski Center with 45 km of trails that are great for skiing, snowshoeing, and fat biking.

For a more affordable option, check into The Shire Woodstock, a riverfront motel with beautifully appointed rooms with fireplaces and cozy linens.

What to do in Woodstock, Vermont in the Winter

Did you know that Woodstock is home to Vermont’s only national park? Marsh-Billings-Rockefeller National Historical Park. Part nature preserve, part history museum, the National Park Service calls this unique park, “the only national park to tell the story of conservation history and the evolving nature of land stewardship in America.” 

Winter is a great time to explore the multi-use trails that crisscross the Marsh-Billings-Rockefeller property (free), as well as the groomed cross-country ski trails ($$) that are maintained by Woodstock Inn and Resort.

Meander around the Pogue, and head up to the Woodstock Star on the South Peak of Mount Tom (1,250 feet). This trail map shows the multi-use trail in yellow, which is free to hike or snowshoe on in the winter.

If alpine skiing is more your speed, head to Woodstock’s beloved local ski mountain, Saskadena Six, which is affordable and great for beginners. Nearby Quechee Club offers downhill skiing, groomed cross-country trails, and an ice skating rink, making it the perfect place to spend a snowy afternoon.

Finally, if you crave a little retail therapy, meander into downtown Woodstock and pop into a few of the many boutique shops, art galleries, and clothing stores.

The Vermont Antique Mall in Quechee is Vermont’s largest antique mall and the perfect spot to step out of the cold and back in time.

Please read our complete itinerary for your winter weekend in Woodstock, Vermont!

Burlington, Vermont

Church Street in Burlington, Vermont in the winter.
Burlington, Vermont in the winter

For a more urban winter getaway in Vermont, your only choice is the relative metropolis of Burlington.

That’s not to say that you can’t partake in dozens of outdoor activities, but those adventures can be bookended with world-class dining, cultural attractions, and shopping. This small, but vibrant city is located on the shores of Lake Champlain with incredible views of the Adirondacks across the lake in New York.

Where to Stay in Burlington this Winter

When it comes to Burlington hotels, we pretty much always choose to stay right downtown so we can get around on foot.

This allows us to take advantage of the restaurants and shopping without constantly having to get in the car. Here are our top choices for lodging in Burlington.

  • Hilton Garden Inn: While I don’t usually recommend large chain hotels, the Hilton Garden Inn in Burlington is impressive in its location, price, and comfort. Even the lobby is beautiful. This Hilton is located on Main Street, just a few blocks from the Church Street Marketplace and the waterfront. It’s also got an indoor pool and fitness center.
  • Hotel Vermont: Located very close to downtown and the waterfront, this is a boutique retro hotel with minimalistic furnishings and a fabulous restaurant. It’s well known for its dog-friendliness, customer service, and high price. Worth it? At least once!
  • Delta Hotels by Marriott: If you want to save some money on lodging, you’ll have to sacrifice location, I’m afraid. Delta Hotels has a lot going for it, though – it’s close to the airport, the rooms are comfy, and there’s an indoor pool and fitness center. Pets are not permitted.

The Best Things to Do in Burlington, Vermont in the Winter

True story – during my college days in Burlington, I would often walk downtown to buy coffee at Speeder & Earl’s on Church Street and walk back to my apartment. On more than one occasion, my coffee actually had a layer of ice on it by the time I had walked three blocks. Burlington in the winter is not for the faint of heart.

Fortunately, there are plenty of things to do indoors and out in Burlington to keep you warm, just don’t get your coffee to go. If you have your own Nordic skis, there are a lot of great spots to take advantage of free ski trails in Burlington.

Cross-Country Skiing and Ice Skating in Burlington

The Intervale grooms seven miles of trails for both classic and skate skiing. It’s totally free and dogs are permitted. Another option is to ski on the side of the Burlington Greenway. The middle is often plowed for walkers, but there is usually plenty of room for classic skis on the path’s edge.

If you are new to cross-country skiing, I recommend starting at Catamount Outdoor Center in Williston, where you can rent skis, take a lesson, and enjoy more than 35 km of groomed trails.

Ice skating is another great way to get outside in Burlington. I grew up ice skating at the indoor rink at Leddy Park, but the six outdoor rinks in Burlington are a great free alternative if you have your own skates.

Indoor Activities in Burlington, Vermont

When the winter winds blow across Lake Champlain and freeze the coffee in your mug, you need to find something to do indoors. We get it! Here are a few indoor activities that we’d recommend checking out while you’re in Burlington.

  • Visit the Echo Center on Lake Champlain: This science and nature museum features live animals, changing exhibits, and a 3D theater. Learn all about the history, geology, and ecology of the Lake Champlain Basin.
  • Take a Burlington Brewery Tour: Most of the craft breweries on the Burlington Beer Trail are within walking distance of each other, but if you don’t want to hoof it, check out the Sip of Burlington Tour, which provides a designated driver and VIP access to local breweries.
  • Check out Burlington City Arts Center: Part gallery, part art education center, Burlington City Arts features rotating exhibits, classes, and open studio time.
  • Go Climbing at Petra Cliffs: This indoor climbing facility in Burlington appeals to every type of climber, even folks that have never done it before. Great for kids and adults.
  • Visit Get Air Trampoline Park: Visiting Burlington with kids? Get Air in Williston is one of the best ways for them to burn off energy indoors. Not only does Get Air have thousands of square feet of trampolines, but they’ve also got foam pits, slack lines, and special events.

Brattleboro, Vermont

The Latchis Hotel at night in Brattleboro, Vermont.
The Latchis Hotel at night.

A winter weekend in Brattleboro is the perfect escape for city dwellers. It’s just three hours from Boston and four from NYC, plus it’s one of the few towns in Vermont with an Amtrak station, so you can easily plan a car-free adventure.

The historic downtown community in Brattleboro is nestled in the foothills on the western bank of the Connecticut River. While the population of Brattleboro is just over 12,000 people, the town embraces an urban identity with eclectic restaurants, live music, theater, and shopping.

Where to Stay in Brattleboro, Vermont

Whether or not you bring a car to Brattleboro, you should stay downtown if you can. There’s only one downtown hotel, but it’s a good one!

The Latchis Hotel is housed in an 80+-year-old Art Deco building. The hotel has tried to retain the historic charm of the building while adding the modern amenities that travelers need for comfort. This is one of only two Art Deco buildings still functioning in the entire state of Vermont.

The Latchis Theatre operates right downstairs and features both Hollywood and Indie films.

If you need a bit more room to spread out, try this cute bungalow with room for five people. It’s just a few blocks from the downtown area and has off-street parking.

The Best Things to Do in Brattleboro in the Winter

If you look beneath the surface in Brattleboro, you’ll find that it has several unique winter gems that you won’t find anywhere else in Vermont.

The first is Harris Hill Ski Jump, which celebrated its 100th anniversary in 2022. Each year in February, ski jumpers gather from all over the world to compete in the annual Harris Hill Ski Jumping competition. This is a celebrated Brattleboro tradition and absolutely worth traveling to Vermont for.

If you are not visiting during Ski Jump weekend, you can still climb the stairs to the top of the jump and wander more than 10 miles of trails at Retreat Farm. Snowshoes or Microspikes might be required.

Another unique and fun experience is a visit to the all-volunteer-run Brattleboro Ski Hill, which got its start in 1937. A 1300-foot T-bar brings skiers to the top of the hill and lift tickets are only $5 per person. Unfortunately, they do not offer rentals.

Indoor Activities in Brattleboro for Winter Fun

As much as we love getting outside year-round, we’re well aware that a fun winter destination needs more than snowshoe trails and ski hills. Aside from some great independent shops, including several bookstores, record stores, and an awesome outfitter, Brattleboro also has some incredibly unique cultural attractions, including:

  • New England Center or Circus Arts: Offering special events and workshops throughout the year, if you’ve ever wanted to learn to juggle, swing on a trapeze, or try wire walking, you may want to check this out. Even if you don’t fancy yourself a circus performer, there are spectator events throughout the year.
  • Brattleboro Museum and Art Center: BMAC is a non-collecting contemporary art museum focused on the work of living artists. Exhibits are housed in six galleries and are rotated every three to four months. The galleries are open Wednesday-Sunday, 10-4.
  • The Stone Church: If you are fortunate enough to be in Brattleboro when there’s a performance at the Stone Church, be sure to buy tickets. This unique performance space has amazing acoustics, and the musical talent is always impressive.

Need more ideas? Check out our complete itinerary for a winter weekend in Brattleboro, Vermont.

St. Johnsbury and the Northeast Kingdom

A person walks through the snowy forest on a Vermont winter getaway.

If you’ve been looking for snow in all the wrong places, it’s time to head a little farther north into Vermont’s Northeast Kingdom.

St. Johnsbury will be your home base for this Vermont winter getaway. Home to 7,500 residents, St. Johnsbury is the largest town in the Northeast Kingdom of Vermont, and the perfect place to experience winter in Vermont. Like many of the Vermont towns in our list, St. Johnsbury has some unique offerings that you won’t find anywhere else.

Where to Stay in St. Johnsbury, Vermont

If you want to stay right in town, Cherry House Bed & Breakfast on Frost Avenue comes highly recommended by everyone who has ever had the pleasure of staying there. This 1901 Victorian Dutch Revival features beautifully decorated rooms, a full breakfast, and delightful hosts. In addition to standard guest rooms, there are also a few cottages available onsite. Pets are permitted for a small fee.

Another unique option is a stay at this spectacular treehouse listed on Airbnb. It’s tucked away in the woods on top of a mountain and is just .5 miles from the famous Dog Mountain. Pets are permitted too, of course.

Read Next: 6 Amazing Treehouse Rentals in Vermont

The Best Things to Do in the Northeast Kingdom in the Winter

Vermont’s Northeast Kingdom is home to two premier ski resorts. If you’re staying in St. J, the closest ski area is Burke Mountain, just 16 miles north.

The nearby Kingdom Trails feature a beautiful network of trails for winter use, including 31 miles of fat biking singletrack, 7.3 miles of groomed cross-country ski trails, and 38 miles of snowshoeing trails. You must purchase a day pass to use Kingdom Trails and dogs are not permitted.

If you don’t have equipment of your own, or just don’t want to bring it all the way to Vermont, you can rent Nordic skis, fat bikes, or snowshoes at the Village Sports Shop in Lyndonville.

Another great option for getting outside? Ice skating!

St. Johnsbury Recreation Department operates two free outdoor skating rinks in the winter: one at the Four Seasons Park on Main Street and the other at the Buck Park on Portland Street: heating huts and lights at each.

The inside of the Dog Chapel on Dog Mountain in St. Johnsbury, Vermont.
The Dog Chapel at Dog Mountain in St. Johnsbury, Vermont

You can’t visit the Northeast Kingdom without paying a visit to Dog Mountain in St. Johnsbury.

Set on top of a mountain with more than 150 acres to explore, Dog Mountain is a place for dogs and their owners to adventure together off-leash. The trails are great for snowshoeing in the winter but don’t forget to stop into the dog chapel to pay tribute to all the pups you have loved and lost.

Indoor Activities in Vermont’s Northeast Kingdom

Planning ahead for foul weather, let’s check out some of the unique indoor offerings in this part of Vermont.

  • Fairbanks Museum and Planetarium, St. Johnsbury: A natural history museum and planetarium with more than 30,000 objects, special event offerings, and the weird and wacky collection of “Bug Art,” created with thousands of beetles, moths, and butterflies, meticulously positioned on wood and framed for your viewing pleasure.
  • Catamount Arts, St. Johnsbury: The only full-service arts center in northeastern Vermont, Catamount Arts is the perfect place to catch a film, a show, or an exhibit.
  • Jay Peak Pump House and Indoor Waterpark, Jay: Jay Peak Resort is another of Vermont’s most adventurous ski mountains, but it also houses Vermont’s only indoor water park, this is the perfect place to come in out of the cold. Jay Peak is located on the Canadian border and is about an hour’s drive from St. Johnsbury.

Stowe and Waterbury

A snow-covered Mount Mansfield in Stowe, Vermont, one of the best posts to spend winter in Vermont.

When it comes to amazing winter destinations in Vermont, most people think of Stowe, which is in the very heart of the northern Green Mountains, and the epicenter for downhill skiing and other outdoor pursuits.

For a quintessential Vermont winter getaway, Stowe is hard to beat, but of course, you’ll be sharing your vacation with others who feel the same way, so be sure to book your reservations well in advance.

Where to Stay in Stowe in the Winter

If you’ve never stayed in the mountains of Austria and want a similar experience, transport yourself to the Trapp Family Lodge in Stowe. Located on 2,500 acres in the Green Mountains, you could spend your entire Vermont winter getaway on the property and be perfectly content.

Where else can you explore miles of cross-country ski trails in the morning, embark on a mountainside horse-drawn sleigh ride in the afternoon, and sip locally brewed beers as the sun sets over the mountains?

The Trapp Family Lodge is a pet-friendly establishment with 96 beautifully appointed rooms and suites.

The Best Things to Do in Stowe in the Winter

Stowe Mountain Resort is one of Vermont’s most iconic ski resorts, with 116 trails on the side of Vermont’s highest peak. If you’ve come to Vermont to ski, then a trip to Stowe Mountain Resort is one of the best things to do in Vermont in winter.

The mountain receives more than 300 inches of snow annually, and the 40 miles of trails are spread over 485 acres. The Cross-Country Center adds an additional 45 km of groomed Nordic trails and another 30 km of backcountry trails. Rentals are available for both downhill and XC skis.

While enjoying Stowe Mountain Resort, be sure to visit the outdoor ice skating rink at Spruce Peak Village. It’s free to use and open to the public.

For guided adventures to all the outdoors has to offer in the area, connect with Umiak Outdoor Outfitters, which offers dog sledding tours, snowshoeing, and ski tours throughout the winter.

Indoor Activities in Stowe and Waterbury

Here are a few more things to do in Stowe and nearby Waterbury when you need to come in from the cold.

  • Ben & Jerry’s Factory Tour, Waterbury: As of early 2022, the factory tours are on hold at Ben & Jerry’s, but the scoop shop is open from 11 am to 6 pm.
  • Spruce Peak Performing Arts Center, Stowe: Spruce Peak Arts is a year-round venue that offers world-renowned entertainment, including live music, art shows, dance, comedy, film, lectures, and emerging artists and performers from around the region, the United States, and the world. Be sure to check their calendar before booking your trip.
  • Vermont Ski and Snowboard Museum, Stowe: Located right in downtown Stowe, this small museum has a mission to collect, preserve and celebrate Vermont’s skiing history.
  • Take a Brewery Tour, Stowe: The Stowe area is another mecca for craft brewing. Let 4 Points Vermont take you around on a tour and tasting. They’ll even pick you up at your hotel!
  • Cold Hollow Cider, Waterbury: Learn how cider is made, snack on cider donuts, visit the gift shop, and do a tasting in the hard cider room!

Visiting Vermont in winter is an amazing experience! Have you ever spent a winter weekend in Vermont? What are your favorite spots for indoor and outdoor fun?

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A collage of photos featuring Vermont winter getaways. Caption reads 6 awesome winter getaways in Vermont.

Tara Schatz is a freelance writer and the founder and editor-in-chief of Vermont Explored and Back Road Ramblers, an American road trip blog. She is also the co-author of the 3rd edition of AMC’s Best Day Hikes in Vermont, released in May 2023, and the author of 100+ Wonderful Ways to Experience Vermont.