A Winter Weekend Guide to Woodstock, Vermont

The idyllic New England town is wonderful in all seasons but particularly magical when blanketed in snow

February 3, 2023 8:37 am
woodstock inn and resort in the winter after snowfall
It doesn't get much prettier than this.
Woodstock Inn & Resort

I’ll admit, I’ve never been a big fan of winter. Although I love New York, every year post December, I lament the cold and would much rather escape it than deal with frigid temperatures until April. But after a recent trip to Woodstock, Vermont, which just might be the most charming town in America, I have a newfound appreciation for the coldest season of the year. 

I arrived on a Thursday afternoon, and by Thursday evening, the snow had already started to make its heavy fall. Come Friday morning, the entire town was blanketed in white, and it was one of the most delightful things I’ve ever seen. The energy was high as both locals and visitors geared up for snow sports, warmed themselves in front of fireplaces and fire pits, and sipped on whiskey and wine to keep extra toasty. If it sounds kind of perfect, it’s because it was —and only the beginning of a beautiful winter season in Woodstock.

The Vermont city is only a four-and-a-half-hour drive from NYC and a mere two and a half hours from Boston, which makes it a perfect place to escape for a long weekend. If you’re in need of a cold-weather getaway — and perhaps a new appreciation for the season — dig into our winter weekend guide to Woodstock, Vermont for everything to do in the charming New England town. 

woodstock inn and resort lobby with wood burning fireplace
The Woodstock Inn & Resort’s lobby fireplace, a perfect spot for cocktail hour
Woodstock Inn & Resort

Stay at a Historic Hotel

Although Woodstock Inn & Resort has been rebuilt since it first opened in 1892, the property boasts a charming, historical elegance and friendly, relaxed atmosphere that will make you feel right at home. All of the guestrooms and suites were renovated in 2018, and there are even some dog-friendly rooms so you don’t have to leave your pet behind. Four-legged friends are welcome to hang with you throughout the hotel, save for the onsite restaurants, both of which are delicious. The Red Rooster serves an expansive buffet breakfast every morning, plus lunch, dinner and cocktails at the cozy bar. Settle into a plush seat in front of the wood-burning fire at Richardson’s Tavern and tuck into warming dishes like fondue and confit duck with cabbage and apple. Much of the produce served at both restaurants is sourced from Woodstock Inn’s very own Kelly Way Gardens. If you’re in need of an afternoon boost, drop by the gift shop from 4-5 p.m. for homemade cookies (the oatmeal raisin is a true revelation), coffee and tea.

There are a ton of cozy nooks throughout the hotel where you can sip a dram or play cards, and there’s even a dedicated game room with billiards, air hockey and vintage arcade games. All guests have access to the Woodstock Athletic Club, which is a two-minute drive down the road. This place has everything you could possibly want in a fitness center — indoor and outdoor tennis courts, weight training equipment, a cycling studio, yoga classes, outdoor trails and an indoor pool with hot tub, sauna and steam room.

drinks on a table at au comptoir bar in woodstock vermont
Drinks await at Au Comptoir.
Au Comptoir

Eat and Drink Around Town

Like a lot of restaurants in Woodstock, Santè is truly farm-to-table — many of the kitchen’s ingredients are sourced from the owner’s farm. The globally-inspired shareable plates have a local lean, like seared sweet potato with olive and chive and Vermont rabbit with Parisian gnocchi, crispy mushroom and Parmesan. Mon Vert Cafe is a local favorite, and in the warmer months, the sidewalk outside the charming A-frame eatery is packed with people waiting for tables. Things are a bit calmer in the winter but no less delicious, and it’s a perfect place to grab breakfast or a hearty sandwich for lunch. At the newly-opened Au Comptoir, take a seat at the long bar, at a cozy corner table or outside by the fire pit. Order a signature cocktail — we’re partial to the Hibernator, made with Michter’s Rye, apple brandy, Vermont maple syrup, house bitters and Amaro Nonino — and salty snacks or local chocolate truffles to share.

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Shop Local

It’s amazing how many quality shops are packed into Woodstock’s two main streets. F.H. Gillingham and Sons has been in operation since 1886 and is still a family-run general store. Set aside ample time to peruse its many rooms where you’ll find everything from local maple syrup, cheese and other provisions to children’s toys to Carhartt gear. Don’t miss the small but mighty wine room where a lot of our time was spent shopping for both new discoveries and old favorites. 

Hop across the street to The Vermont Flannel Company for some of the softest, highest quality flannels we’ve ever worn. While the fabric is sourced in Europe, each garment is actually hand-cut and sewn in the United States. If you forgot any mountain gear or need quality activewear, Elevation Clothing carries brands like Blundstone, Patagonia and Cotopaxi.

Whether you’re shopping for a gift or just want to treat yourself to something nice, Woody’s Mercantile has a well-curated selection of kitchen and tabletop goods, home bar essentials, candles, art, decor and more. It’s easy to spend hours in Yankee Bookshop perusing every nook and cranny of books, stationary and vinyl, where we snagged the recently remastered and repressed Nancy & Lee album. Recreational cannabis is legal in Vermont, so take a quick ride to Sunday Drive where the helpful staff will guide you on the best flower, edibles and accessories to sample. 

the mill restaurant at simon pearce
The Mill restaurant at Simon Pearce
Simon Pearce

Take a Quick Trip to Quechee 

Located a mere 15-minute drive from Woodstock, Quechee is a small Vermont village that’s known for its beautiful surroundings. It’s also the location of the Simon Pearce flagship store and glassblowing studio where you can watch the brand’s talented artisans at work. With an onsite restaurant and bar, it’s easy to make a night out of the experience.

Start by perusing the retail store for fancy drinkware, pottery and other home goods. Afterwards, mosey downstairs to the glassblowing studio where you can watch Simon Pearce’s expert artisans at work. Don’t forget to step outside the back door for an up-close look at the Ottauquechee River waterfall, but the best view of the falls can be enjoyed in the dining room of Simon Pearce’s onsite restaurant, the Mill. Sip on a beautiful cocktail while snacking on a Vermont cheese plate or digging into a main, like the cider-brined pork chop. Reservations are highly sought-after, so make sure you plan ahead. If you don’t have a res, the bar takes walk-ins.

After dinner, follow the path to the historic Parker building next door. Climb the stairs to the second floor and take a seat in the cozy WhistlePig Whiskey Parlour, a tasting room experience where you can sample your favorite expressions, plus a few harder-to-find bottles (we’re partial to the 15 Year Estate Oak Rye Single Barrel). Make a reservation to ensure you get a seat.

Enjoy the Fresh Powder

Vermont often conjures visions of snow-capped mountains and warming libations by wood burning fireplaces. The state’s reputation as a winter wonderland is obviously spot-on, and Woodstock offers the best of snowy activities. Saskadena Six is only an eight-minute drive from the center of town and has 24 trails to enjoy. It’s a smaller mountain, but there are enough runs for both beginners and advanced skiers and snowboarders. If you’ve never skied before (like this particular writer), a private lesson with one of the excellent instructors will have you flying down the bunny hill in no time. Onsite Perley’s Pourhouse offers a lively après ski scene that’s often punctuated by live music. If you’re looking for higher elevation with significantly more trail options, Killington is only about 30 minutes from Woodstock. But if downhill isn’t your thing, Woodstock Nordic Center has 45 kilometers of groomed trails that are perfect for snowshoeing, cross-country skiing and fat biking, and both lessons and guided tours are also available.

Come Back in the Spring, Summer or Fall

Woodstock is a stunning locale in all seasons, so if you love it as much as we do, you’ll definitely want to come back for warm-weather al fresco dining and fiery fall foliage. Everything in this guide (save for the snow sports) is wonderful year-round, but once the town has thawed, make sure to visit Billings Farm & Museum, hike the Mount Peg Loop, and try activities like fly fishing and falconry. 


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