Winter Weekend in Woodstock, Vermont | Weekend Away

Fall in love with winter in a handsome little town brimming with cold-weather adventures and amenities.

By Amy Traverso

Dec 03 2020


Winter light over downtown.

Photo Credit : Andrew Rowat

TRAVEL NOTE:Since many businesses and venues are adjusting their operations in response to COVID-19 health concerns, please contact them directly or check their websites before making travel plans.

Winter light casts a glow over downtown Woodstock, Vermont.
Photo Credit : Andrew Rowat

Winter can wear down even hard-boiled New Englanders. Many tolerate it, others take refuge in skiing, skating, and snowmobiling, while snowbirds flee southward. But there is a special subset who relish the deep snow shoveling, the long nights, the nipped cheeks and frozen toes. And if you aspire to join their ranks, there’s no better way to fall in love with this season than to spend a weekend in Woodstock.

First, there’s the snow. Woodstock sees more than 80 inches a year (twice as much as Boston, three times more than Hartford), so if you’re driving up on a Friday night, there’s a good chance you’ll roll into town with a fresh blanket crunching under your tires and flurries swirling in the air. You’re off shoveling duty, so slow down and notice the frost framing the shop windows, which are kept illuminated with twinkle lights long after Christmas.

Next, there’s the concentration of top-notch lodging, shopping, and dining options, remarkable for a town of just 3,000 year-round residents. The most committed city dweller will have no quarrel with a fine dinner followed by an art-house movie at the Town Hall Theater.

Finally, there are the locals themselves, many of whom are young and sporty types lured here by the rolling hills, good schools, and urbane amenities. Seeing young families sipping cocoa after a regional ski meet at the local mountain, Suicide Six, you may even be tempted to move here yourself.

So if the post-holiday weeks of January are looming before you like a threat, give in. Embrace the cold. Let Woodstock show you how.

Freshly renovated in 2018, the Woodstock Inn & Resort is a luxury escape with roots that reach back to 1892.
Photo Credit : Andrew Rowat


If you’re feeling hungry on your arrival, Worthy Kitchen is the perfect stop for a stellar burger and top-notch local beers, including cult favorites like Hill Farmstead and the Alchemist. Since Woodstock’s foliage season has long passed, getting a table is easier—as is finding a good hotel room (though if your visit falls in a holiday or school vacation week, book ahead).

The Woodstock Inn & Resort is the grande dame, presiding over the town green and welcoming travelers with a roaring fire. Between its plush beds, on-site spa, and off-site health club down the road (with heated pool and sauna), this is the prime destination for sporty types and hibernators alike. If you prefer more of a B&B feel, however, the nearby Woodstocker delivers on style—and breakfast in bed too.

West of town, the Lincoln Inn & Restaurant at the Covered Bridge is a romantic white clapboard farmhouse whose award-winning restaurant ensures you’ll hardly need to leave your cocoon. You can’t quite walk to town from here, but Farmhouse Pottery, the rustic-modern Vermont lifestyle brand, has its flagship store just down the street. Meanwhile, families flock to 506 On the River Inn for its indoor pool and farmhouse suites, complete with kitchens.

Starting the day off right at local hangout Mon Vert Café.
Photo Credit : Tara Donne


Most inns here offer breakfast, all quite good, but to caffeinate with the locals, head to Mon Vert Café, which specializes in “rustic, local, country food and good strong coffee.” That translates to terrific breakfast sandwiches, yummy muffins, and cozy lattes (regular, matcha, or chai).

If you’ve come to ski, there are few mountains more charming than the incongruously named Suicide Six. It’s actually a fairly low-octane spot to learn the sport (the instructors are terrific) or spend a day doing runs on its 24 trails (snowboarders welcome). Free of the crowds found on larger mountains, it boasts a hometown charm, as well as the distinction of being one of the country’s oldest ski areas and the home of the first rope tow, which must have seemed sport-changing at the time.

Pint-size skiers at Suicide Six.
Photo Credit : Tara Donne

Cross-country skiers and snow-shoers, meanwhile, can take advantage of the groomed trails maintained by the Woodstock Inn at its Nordic Center. These converge with the paths that snake up Mount Peg and Mount Tom, so you can add as much elevation as your skill set allows.

Such exertions merit a hearty lunch, and the Mountain Creamery will fill you up with its famous VerMonte Cristo sandwich (ham, turkey, and Swiss on egg-dipped bread, served with maple syrup), mile-high apple pie, and homemade ice cream. It’s located in the heart of the village’s commercial district, so don’t miss the opportunity to visit the Yankee Bookshop, a fixture since 1935. Across the street, Sudie’s specializes in modern-preppy-meets-Vermont-chic clothing, and Unicorn is a great place to get lost amid a heaving inventory of fine jewelry, toys, home accents, and gag gifts.

A window filled with snow-day reading inspiration at the Yankee Bookshop.
Photo Credit : Tara Donne
Neapolitan-style pizza at the Ransom Tavern.
Photo Credit : Tara Donne

Looking for more outdoor adventure? The Vermont Institute of Natural Science in nearby Quechee hosts a winter wildlife weekend in January, as well as live raptor programs, wildlife rehabilitation workshops, and a wheelchair-accessible forest canopy pathway that gives visitors a bird’s-eye view of the woods.

Cap off your day in town at the Daily Catch, the unlikely Vermont outpost of Boston’s favorite Italian seafood restaurant (the Freddura family bought a country house up here and decided to expand north). Or, head to South Woodstock, where the Ransom Tavern in the Kedron Valley Inn serves excellent Neapolitan-style pies and antipasti in a modern tavern setting.

Heading off on an old-fashioned sleigh ride at Billings Farm & Museum.
Photo Credit : Joel Laino


As the weekend winds down, it’s time to go deep on Vermont charm. Start with Woodstock’s iconic general store, F.H. Gillingham & Sons, a rambling 135-year-old mercantile that sells everything from French wine to Carhartt essentials. Ounce for ounce, a gallon of maple syrup here is a solid deal compared with those little glass bottles back home, and the toy and home goods departments should take care of any gift-giving you need to do.

For a glimpse into 19th-century Vermont life, spend a few hours at Billings Farm & Museum, which captures the moment when dairy farming emerged as one of the state’s dominant industries. Established in 1871 and now overseen by the Rockefeller Foundation, the farm is still home to a thriving herd of Jersey cows, plus Berkshire pigs and Southdown sheep. Visitors can wander through the fields and barns, sample cheese made from the farm’s own milk, and, on special weekends, take sleigh rides pulled by draft horses.

A staff artisan at work at Miranda Thomas Pottery.
Photo Credit : Tara Donne

Before hitting the road, swing by the Woodstock Farmers’ Market for some road snacks. This indoor market highlights the most noteworthy Vermont-made foods, from cheeses and jams to bread and chocolate; many aren’t sold beyond the state’s borders, so stock up. While you’re at this end of town, don’t miss Shackleton​-Thomas, where furniture maker Charlie Shackleton and potter Miranda Thomas make and sell their wares. These heirloom pieces offer a vision of the slower, more handmade life that draws all those young families to town. And if you’re feeling sad to leave, you might even consider joining them.

More Photos from a Winter Weekend in Woodstock, Vermont

Middle Bridge, one of Woodstock’s three historic covered bridges.
Photo Credit : Justin Cash
A cozy corner of the Woodstock Inn & Resort.
Photo Credit : Tara Donne
A rustic-chic guest room at the Woodstocker B&B.
Photo Credit : Tara Donne
Handmade wares at the South Woodstock Country Store.
Photo Credit : Tara Donne
A colorful nook at Miranda Thomas Pottery, one half of the ShackletonThomas studio-showroom complex.
Photo Credit : Tara Donne
Billings Farm & Museum offers the chance to get up close with the barnyard set.
Photo Credit : Tara Donne