Winter in Woodstock

Woodstock Vermont, birthplace of the ski lift in North America, has no shortage of things to do in the winter. Here are a few favorites (scroll down for visits and events). Feel free to call or email if you have questions. 

Woodstock and The Woodstocker featured in Yankee Magazine

Follow in the footsteps of the iconic magazine as they spend a winter weekend in Woodstock, Vermont

And read their praise of The Woodstocker B&B for delivering on style, and breakfast in bed, too!


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

Yankee Magazine, Jan/Feb 2021

Outdoor Snow Fun

  • Saskadena Six (a 10-minute drive from the B&B), is a smaller and sweet resort with a nice mix of beginner, intermediate, and advanced trails, a super cozy lodge complete with massive fireplace, bar, food, rentals, and shop.
  • Killington, aka The Beast of the East, is the Northeast’s largest ski resort and is open for skiing and riding from late Fall to the Spring. In 2019, Killington will be once again hosting the Women's World Cup over Thanksgiving weekend. Its Skyeship gondola is only 20 minutes from The Woodstocker B&B, while the base lodge is a 30-minute drive.
  • Pico Mountain is a little past Killington. It was one of the first commercial ski resorts in the state.
  • Okemo Mountain is less than a 40-minute drive south of Woodstock.

top of a slope with one skier and large open view on mountains

View from the top of Killington

View from the top of Killington[/caption]

The Nordic Center, 1 mile from the B&B, offers 45 kilometers of beautifully groomed trails which span Mount Peg and Mount Tom.

Lessons and tours are available and should be booked in advance. Equipment rental on site.

Groomed snow trail on flat expanse with hills in the background

The Nordic Center offers groomed trails for cross country ski, fat bike and snow shoeing

Snowshoeing can be as peaceful or athletic as you want! It is a wonderful way to discover the outdoors right from the front door of our B&B when the snow blankets Woodstock! The trails at the Marsh Billings National Historical Park , on Mount Tom and Mount Peg, are wonderful for snowshoeing (trail fees apply). And after a snow storm, the town is your playground!

  • We have snowshoes and poles available to borrow. Simply bring a pair of waterproof, comfortable shoes, warm clothing, and you are on your way for some simple winter fun!
  • Or, head over to the Nordic Center, rent equipment there or bring your own, and enjoy miles and miles of groomed and marked trails. On Saturdays, the Nordic Center organizes a snowshoe trek to Mount Tom Cabin where a warm soup awaits!
vertical view of trees against blue sky Snowshoes in snow

Killington Mountain offers a multi-lane, lift-serviced tubing park open Friday evening, Saturday, Sunday, and holidays, starting Dec 21, 2019 to March 29, 2020 (conditions permitting). Check out their website for more information.

The tubing park is about 30 minutes from The Woodstocker.

On your way to Killington, why not stop at Shackleton Thomas or Farmhouse Pottery for some quality shopping or just to browse through the creations of high end artisans, and at Long Trail Brewery for a sampling of Vermont beer? On your way back, a pizza at Ramunto's could be just what you need -- or order it and enjoy it at the B&B!

laughing woman sliding down on a snowtube

With 2 departure locations less than 20 minutes from The Woodstocker, Snowmobile Vermont offers:

  • one-hour mountain tours that will take you through the woods on groomed ski trails.
  • two-hour back country tours on 25 miles of trails through the Calvin Coolidge State Forest, on the Vermont State Trails system, offering varied terrain.

Contact Snowmobile Vermont for more information and to book your tour. And get ready for some wicked awesome fun!




Fat Bikes are bicycles equipped with very large tires that grip the snow and ice, letting you tackle groomed trails going down or up. In Woodstock, they are available for rent at the Nordic Center. Group or semi-private tours are also available. Trail fees apply. Please click here for more information.

Vermont Bike and Brew  now offers electric fat bikes, which adds the convenience of an e-bike to the fun of a fat bike. Contact them to arrange delivery and discuss best trails. 

In 2018, Suicide Six hosted the first fat-biking slalom in the Eastern US.

Kedron Valley Stables in South Woodstock offers sleigh or carriage rides depending on the season and weather. Please call (802) 457-1480 to make your arrangements.

Billings Farms and Museum offers sleigh rides on select dates. Please check their website (https://billingsfarm.org/)


Over the weekend surrounding the 2nd Saturday in December, Woodstock celebrates the beginning of the holiday season with a horse-drawn carriage parade, caroling, wassailing (aka warming up with hot mulled cider), concerts, and more. Visit historic homes on the Green and Elm Streets, and get your shopping done in a picture-perfect New England town all decked out for the holidays. Nothing comes closer to Christmas in Vermont! The celebration of Wassail is a weekend-long event. Book early!



When the days are warmer and the nights still cold, the sap flows through the maple trees, ready to be collected. Throughout Vermont’s magical winter landscape, thin billows of smoke signal sugar houses — where the collected sap is boiled down to syrup, with nothing added and only water removed.

Come visit these sugar houses, talk to the Vermonters who make the world’s best syrup, and partake in fun activities throughout our picture-perfect town.

The Woodstocker B&B with Christmas lightsWe are open for Christmas and New Years.

Feel free to contact us as we get closer to these dates to find out about dinner options and making reservations, whether you’d like a full on celebration or nothing special!

Winter in Woodstock was last modified: June 2nd, 2024 by Isabelle Chicoine