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. 

Outdoor Snow Fun

  • Suicide 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.
  • 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

Experience the thrill and magic of dog sledding through beautiful nature. Breaburn Siberians will take you on an unforgettable adventure in the Windsor, VT / Claremont, NH area! They offer:

  • 30 minute rides
  • 90 minutes excursions
  • or, customize your own experience; night ride, proposal, etc.

Dog sledding is very popular, so be sure to book online or contact them for your customized experience.

Huskys and Musher, front view

huskys pulling a sled with trees and skyline in the backgroundPhoto credits: Breaburn Siberians

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 Shackelton 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.

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



Billings Farm & Museum is a must-see in Woodstock, VT.

Start your visit by watching a 30-minute documentary which will give you an overview of the history of Woodstock as it relates to sustainable farming and environmental conservation. You will learn about the families who owned the estate and how they left an indelible mark way beyond our town and countryside.

Then, browse through an impressive museum of farming in Vermont in the 19th century. We guarantee you will not be disappointed!

Follow that with a tour of the farmhouse, and then pay a visit to the animals, especially Billing Farm’s famous Jersey cows.

Start your day with a visit to Billings Farm, then continue with lunch in town followed by some quality shopping in all of Woodstock’s independently-owned shops!

Bilings Farm & Museum is open every weekend and on holidays throughout the winter. 

The Vermont Institute of Natural Sciences is an avian wildlife rehabilitation center and an environmental park located in Quechee, less than 20 minutes from The Woodstocker B&B. They offer special presentations at different times of the day, and you are welcome to take self-guided visits all day long. A new canopy walk open in October 2019 gets you even closer to the trees! A visit not to be missed when you stay in Woodstock, VT.

VINS is open 7 days a week, year round.

Vermont is the state with the most micro-breweries per capita in the country! The best way to discover these world-class craft breweries, as well as some great distilleries and hard cideries, is with a guide who knows all the right places, the most scenic routes, and will take care of the driving!

Please visit this page to learn more about a Brewery & Distillery tour, then reach out directly to Vermontology to book.

The New England Falconry located in Woodstock, VT is a unique opportunity to experience the handling of a Harris’ hawk. Various types of sessions are offerered, from 45 minutes to 2 hours. Click here to learn more and register.


General Store

Gillingham’s. Founded in 1886, this is a must-visit for anyone staying in Woodstock. A genuine Vermont general store, where you will find anything you need (including a nice wine selection).

Art galleries

Gallery on The Green

Woodstock Gallery

Fox Gallery Fine Arts

The Art Collaborative

Fossil Glass


The Vermont Flannel Co.



37 Central


Encore (high-end consignment)

Who is Sylvia (vintage)

Elevation Clothing

Woodstock Sports

Home Décor, Gifts and Specialty

Clover Gift Shop: home décor, gifts, and now a line of CBD products (+ workshops and presentations)

RT Home


Danforth Pewter

Red Wagon (toy shop)

Jewelry Stores

N.T. Ferro


The Art Collaborative, Danforth Pewter, Unicorn, and the clothing boutiques also carry jewelry.

Beer, Wine and Alcohol 

Enjoy our BYOB policy! The Woodstocker B&B provides glasses, ice buckets and an ice machine, as well as bottle openers for the enjoyment of your personnally purchased alcoholic beverages anywhere on the property.

Hops and Barley (at the East entrance of town) has a wonderful selection of local craft beers. If you don’t shop there for yourself while in Woodstock, consider stopping on your way home to bring back some hard to find beers.

Vermont Liquor store, also on route 4 East

Gillingham’s on Elm Street.

The Village Butcher on Elm Street.


This is just a selection of stores a discerning shopper might want to visit while in Woodstock.

In or Towards Bridgewater (route 4 West)

Shackleton Thomas

Farmhouse Pottery

In or Towards Quechee (route 4 East)

Andrew Pearce bowls

Simon Pearce glass

Cabot Cheese and tasting station

Vermont Antique Mall


Deirdre Donnelly jewelry

Vermont Spirits

Fat Hat Clothing Co.

In Windsor’s Artisan Park (route 5 south)

Blakehill preserves

Vermont Famstead Cheese

Silo Distillery

Harpoon Brewery

In Weston, on Scenic Route 100 (south)

The Vermont Country Store


For an updated list of local restaurants, both within walking distance of The Woodstocker or within a short walk, please visit this page.


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: March 16th, 2020 by Isabelle Chicoine