Vermont infallibly feels cozy, whatever the time of year. Winter undoubtedly takes the cider doughnut, though: nostalgic towns decked out for the holidays, après-ski haunts with fireplace seating, enchanting historic inns, and snow-filled scenery. There’s a reason Vermont villages are considered “Hallmark movie towns.” With more than 20 ski resorts across the state and countless protected lands for outdoor recreation, it offfers plenty of ways to play in the snow, too.
Having grown up less than an hour from the Vermont border in Upstate New York, and after living in Burlington for several years, I’ve spent time exploring the entire state. As a photographer, I’m lured by the yearly autumn foliage, criss-crossing rural roads, camera in hand. I love waterfall chasing in the spring or hiking in the summer, and uncovering natural swimming holes. But nothing captures my heart like a Vermont winter. There’s something pure and magical during this season—the childlike wonder of it all.
The best way to experience Vermont is by car, so if you’re planning to fly to the Northeast region, I’d recommend getting a rental car upon landing. Driving in Vermont during the winter months can be tricky, especially if you’re not used to snowy or icy conditions. The president of the Woodstock Inn & Resort, Bruce Grosbety, advises building flexibility into your trip.
“Be prepared to add another night if there’s a snowstorm,” he says. “Our weather is unpredictable, and we always use caution on the roads during winter. If you have to stay another night, the plus side is there’s nothing like waking up to a fresh snowfall.”
While there are ample worthwhile spots to visit in Vermont, this four-day journey through the state stars the places that always have me coming back for more.
Day 1: Gallery hopping and pottery spinning in Wilmington
Peruse the galleries and shops on Wilmington’s cozy Main Street.
Photo by danf0505/Shutterstock
- Breakfast sandwiches and blueberry pancakes at Dot’s of Vermont
- Maple meat sandwiches at River Valley Market
- Dinner at Alpenglow Alpine Bistro
- Browse art galleries in Wilmington
- Take a pottery class at the Uncommon Robin
- Ski or tube at Mount Snow Ski Resort
- Après-ski at Snow Republic Brewery
Morning: Shops in Wilmington
Sandwiched between Bennington and Brattleboro, the town of Wilmington is one of southern Vermont’s tiny treasures. Wilmington is like a Vermont charcuterie board, with a little bit of everything to snack on displayed in an artful arrangement. Start your day off right with breakfast at Dot’s of Vermont, a lively old-school diner popular with locals and visitors alike. Fuel up with the McDot, its classic breakfast sandwich with Vermont cheese, or the blueberry pancakes topped with real Vermont maple syrup, of course.
Next, wander the appealing downtown, popping into a smattering of galleries. View Vermont landscape paintings at the Jim McGrath Gallery, then dip in to Arthouse, an artisan collective space housed in a 200-year-old Greek church.
Local Susan Motyl, owner of Alpenglow Alpine Bistro, suggests taking a pottery class at the Uncommon Robin as “the perfect winter activity.” The studio offers a variety of hands-on workshops, from private lessons to Paint & Sips, where you put your personal creative touch on bisque mugs and bowls.
Afternoon: Ski at Mount Snow
The afternoon is your outdoor oyster. Head to River Valley Market for a made-to-order sandwich from the deli (try the maple-meat-stacked Vermont Club). Then forge on about 10 minutes north to Mount Snow Ski Resort, where you can buy a half-day afternoon ticket at the window (subject to availability, as they can sell out). There is also a tubing park, if that’s more your speed.
En route back to Wilmington, enjoy a post-ski brew and snack at Snow Republic Brewery. The double-fried wings and a crisp Kolsch Pond Skim hit the spot.
Evening: Alpine dinner
Check into the boutique hotel the Vermont House and enjoy a quick refresh before heading to an après-ski-style evening of dinner and drinks at Alpenglow Alpine Bistro, where the music and vibe are very much mountain chalet. Motyl says you can expect “alpine-inspired dishes featuring fondue, Wiener schnitzel, bratwurst, and French onion soup.” Order a festive cocktail like the Winter Alps, a concoction of brut rosé, blood orange vodka, and cranberry, to sip while you check out the menu.
Day 2: Shopping, eating, and horse-drawn sleighs in Woodstock
Long Trail Brewing Company has hearty sides to pair with its drinks.
Photo by Lauren Breedlove
- Pastries and coffee from Starfire Bakery
- Craft beers and lunch at Long Trail Brewing Co
- Dinner at Richardson’s Tavern
- Ride on a horse-drawn sleigh at Billings Farm & Museum
- Browse shops downtown like Yankee Bookshop and Woody’s Mercantile
- Wander the Forest of Lights
Morning: Scenic drive and sleigh ride
Rise and shine with a coffee and a pastry to go from Starfire Bakery (the flaky bear claws and custard-filled pasticciotto are phenomenal), and hit the back roads on your way to Woodstock. The drive along forest-fringed Routes 100 and 106 North, with sprawling farms and covered bridges, is an activity unto itself. In a little under two hours, you’ll pull into a real-life postcard.
“Woodstock has been called ‘the prettiest small town in America,’” says Grosbety. “But what makes it special goes far beyond the aesthetics of the village. Winter feels warm here with the welcoming care and charm of the people, the great snow sports, and the quiet culture that allows you to slow down and experience all that is around you.” Truly, Woodstock is one of those places that just feels snug, even when the windchill dips into negative degrees.
Head to Billings Farm & Museum, where you can hop on a horse-drawn sleigh ride through snow-covered fields, peruse the Vermont-centric exhibits, or say hello to the resident farm animals.
Afternoon: Long Trail Brewery and Woodstock shops
It’s time for lunch; enjoy the hill-studded eight-mile drive along the Ottauquechee River to Long Trail Brewing Co. For the ultimate Vermont winter brewery experience, reserve one of the riverside sugar sheds for $25. You’ll need to bundle up, but there is a small heater, full service, and they’ll even bring a Vermont Flannel dog bed for your pup, if you have one in tow.
Post-lunch calls for a wander in town, and lucky for you, Woodstock has no shortage of cute local shops. Browse books at Yankee Bookshop, souvenirs at Woody’s Mercantile, and artwork at Collective the Art of Craft. If strolling among twinkly lights sounds romantic, head to the Vermont Institute of Natural Science for its annual Forest of Lights (November–January).
Evening: Hearty dinner
Check into the Woodstock Inn & Resort, an 1800s-era New England hotel. When it comes to dinner, Grosbety advises, “Don’t opt for your go-to and ‘safe’ classic this time of year.” He says the on-site Richardson’s Tavern serves hearty winter dishes, “from our maple old-fashioneds at the bar to rich cassoulets (a slow-cooked French stew), and even warm vegetable plates like the Brown Butter Parsnips. The flavors of winter are exceptional.”
Day 3: Hit the slopes in Killington and relax in Stowe
Killington is famous for some of the best skiing on the East Coast.
Photos by Michelle Heimerman
- Coffee and doughnuts from Farmer and the Bell (Woodstock)
- Lunch at one of Killington’s eateries
- Take-out dinner from Raja Restaurant
- Skiing or snowboarding at Killington Ski Resort
Morning: Doughnuts to go
Head out of Woodstock bright and early, but not without getting some of the best doughnuts I’ve ever had at the Farmer and the Bell. Choose from French crullers in flavors like lemon coconut, maple, and apple cider crumb.
Afternoon: Ski at Killington
The first portion of the drive today takes approximately 40 minutes and lands you at one of Vermont’s top ski resorts: Killington, otherwise known as “the Beast of the East.”
In between runs, grab lunch at one of the many eateries serving various dishes from warm slope-side waffles to jerk chicken.
Evening: Drive to Stowe and Indian takeout
After skiing, it’s worth setting aside two hours to get back on Route 100 and drive (past the roadside waterfall Moss Glen Falls) to Stowe. Here, you can settle into your room at the Brass Lantern Inn, a family-run bed-and-breakfast in an early 19th-century farmhouse.
For a restorative dinner, owner of Brass Lantern Inn and restaurant Michael’s on the Hill Andrew Kohn recommends his favorite hidden gem spot, “Raja Restaurant; a take-out only Indian restaurant next to the famous Stowe church.”
Day 4: Everything snow and après-ski in Stowe
Spend your monring snowshoeing at Smugglers Notch.
Photo by Lauren Breedlove
- Breakfast at Butler’s Pantry
- Aprés-ski cocktails at Après
- Dinner at Michael’s on the Hill
- Snowshowing at Smugglers’ Notch
- Skiing/snowboarding at Stowe Mountain
Morning: Snowshoe past waterfalls
After a restful night’s sleep, it’s time for more adventures in Stowe. Kohn suggests a hearty breakfast at the Butler’s Pantry, where the homemade biscuits are sublime.
Then embark on a one-of-a-kind snowshoeing experience. Smugglers’ Notch is known for its narrow mountain pass with giant boulders, waterfalls, caves, and hiking trails. While it’s closed to vehicle traffic during winter months, it is open for snowshoeing. Rentals are available at A.J.’s Ski & Sports.
Skiers and snowboarders can instead opt for the slopes at Stowe Mountain.
Afternoon: Après drinks
Post-snowshoe, Kohn says the cocktails downtown at Après are not to be missed. Warm up with a Tom Cat Toddy, which swaps traditional whiskey with local Vermont Barr Hill Gin, and adds an amaro apéritif twist, and nibble on the locally sourced cheese plate.
Evening: Farm to table dinner
Get spiffy for this evening’s dinner, as you’re in for a real treat at Michael’s on the Hill in neighboring Waterbury (a 10-minute drive). The farm-to-table winter menu celebrates everything local: a salad with baby greens and red wine–poached pears, with a maple balsamic vinaigrette, and chicken coq au vin are among the seasonal offerings. A festive gingerbread margarita is the perfect finishing touch.
“Stowe is amazing year-round,” says Kohn, “but in winter, we come alive.”
