Things To Do in Woodstock, VT This Winter
Wassail Weekend
Wassail is Woodstock’s premiere holiday event and 2024 is the 40th Annual Wassail Weekend, December 13th-15th. It is a festive and fun event that draws big crowds and inspires the magic of the season. Throughout the weekend enjoy scavenger hunts, carriage rides, a historic Victorian Christmas, a parade, and more! The town is bustling with holiday cheer and it’s an event that cannot be missed! See below for events you won’t want to miss this Wassail Weekend! For more information about Wassail Weekend in Woodstock 2024 see our post.
Wagon Rides at Billings Farm
Experience the beauty of Billings Farm from a horse-drawn ride, pulled by their hearty team of draft horses. Both wagon rides and sleigh rides are available on select days throughout the year, conditions permitting.
Simon Pearce Glass Blowing
Experience the awe of glass blowing at the Simon Pearce Flagship store in Quechee, VT. Simon Pearce is a short 15-minute drive outside the village of Woodstock. Glassblowing can be viewed daily, Monday - Tuesday, 10 am - 4 pm, and Wednesday - Sunday, 10 am - 6 pm. While you’re visiting, make reservations for lunch or dinner in the restaurant overlooking the falls, grab a drink at their chic bar, and purchase some holiday gifts in the store.
Cross Country Skiing
Woodstock has a great network of Cross Country Ski trails accessible throughout town. The Woodstock Nordic Center, part of the Woodstock Inn & Resort, is an oasis for all things cross country, fat biking, and snowshoeing. See the website for trail maps, conditions, and pass info. The trails are diverse and great for beginner to advanced levels. You can also access a more advanced network of trails via the Marsh-Billings-Rockefeller National Historical Park.
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Hiking Trails
For those looking for a wintery adventure on the trails, Woodstock has plenty of winter hiking options. Explore the trails in the Marsh-Billings-Rockefeller National Historical Park on Mount Tom or venture to Mt. Peg on the other side of town. Both trails are within walking distance from the village. There are several access points and varieties of trails. Check maps and plan your route taking conditions into account. Conditions during the winter can be wet, slushy, icy, and snowy. Wear appropriate attire and footwear.
Shopping
Woodstock is known for its quaint village with unique and charming boutique shops. Load up on holiday gifts, Vermont souvenirs, and outdoor gear at some of our favorite downtown shops. Check out, Shop Local: A Woodstock Village Guide for a more detailed take on all you need to know for shopping in the Woodstock Village.
Downhill Skiing & Snowboarding at Saskadena Six
For a family-friendly outdoor adventure head to Saskadena Six, one of the longest-operating ski resorts in America! The magic carpet is a great place to introduce the sport to your little ones and trails range from beginner to advanced for those looking for a challenge. Enjoy delicious food and drinks on their outdoor patio with a roaring fire overlooking the slopes.
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Spa Day
There is nothing cozier on a snowy winter day in Vermont than a morning or afternoon at the spa. Head to the Spa at the Woodstock Inn & Resort for a day of luxury and relaxation. Enjoy the whirlpool, sauna, steam room, gorgeous great room with a wood stove, and the treatment of your choice. If you're looking for something more intimate, book with celebrity facialist and Woodstock-local Abigail Zsenai for a bespoke luxury skincare treatment in her cozy space along the Village Green.
Cozy Drinks and Farm-To-Table Food
Enjoy a warm seasonal beverage from Mon Vert Cafe, like their Gingerbread Latter or a hot toddy from Au Comptoir. Their craft cocktails cannot be beat, enjoyed on the patio fireside or in the cozy indoor quaint French cocktail bar. Sante is the perfect destination for seasonal farm-to-table small bites, entrees, and craft cocktails. For more food and drink options in Woodstock, see our dining guide.
Brewery Tour
Check out local breweries in the area with a self-guided tour. Long Trail Brewery in Bridgewater, River Roost in White River, and Harpoon Brewery in Windsor make great apres stops post outdoor adventure. During the winter months, Long Trail offers outdoor sugar shacks you can rent for parties of 4-8 to dine outdoors.
Special Events this Winter in Woodstock, VT
See our full events calendar here.
Torchlight Snowshoe at Billings Farm & Museum
Experience a winter evening at the farm with an after-hours adventure along the illuminated Billings Farm loop. Along the way hear fascinating stories about local wildlife, the land’s history, and its past inhabitants. After exploring the trail, families and friends can gather by the outdoor fire to enjoy storytelling and complimentary s’mores, hot cocoa, and coffee. Find tickets and more information here.
Dates: Friday, January 17 and Friday, February 14.
Apres Ski at Saskadena Six
Saturday evenings in February and March enjoy live music, local beers from Perley's Pourhouse, and great eats at Saskadena Six! Cozy up by the fire after a day on the slopes.
Dates: Saturdays in February and March, 3:30-5pm
Winter Naturalist Series at Marsh-Billings-Rockefeller National Park
Join a Park Naturalist on a guided snowshoe hike or cross-country ski in the Marsh-Billings-Rockefeller National Historical Park this winter. All levels are welcome for both snow sports to explore the trails and discover winter wonders in nature. Pre-registration required, more information here.
Dates: Wednesdays 10am-12:30pm in January and February
Fireside Après Ski at the Nordic Center
Enjoy live music fireside at the Fairway Grill restaurant and bar at the Woodstock Nordic Center.
Dates: Select Saturdays and Sundays, January-March
Fisk Trophy Race at Saskadena Six
Saskadena Six is host to the longest-running ski race in North America, The Fisk Trophy Race, which is a rite of passage for serious Eastern ski racers. This year's Fisk Trophy slalom race, the 88th running of the event, proves to be the embodiment of why ski racing is so easy to love. The race has been in existence since 1937 and is the oldest alpine trophy race in North America. More details here.
Date: February 2
President's Week Torchlight Parade & Party
Celebrate winter with Saskadena Six. Sign up to ski down The Face and create the magical parade of lights, or bring the family and enjoy the view. Torchlight Parade will begin shortly after sunset followed by family festivities, Top Hat Entertainment cranking out tunes, and a cash bar. More details here.
Date: February 15, 4-8pm
