From The Blog 25 Things To Do in Woodstock, VT This Winter

Winters in Woodstock, Vermont are both cozy, charming, adventurous, picturesque and magical. Bundle up and don’t let the cool weather deter you, because Woodstock has something for everyone to enjoy. Cozy up by the fireside with a good book, hit the slopes, relax at the spa, or hit the streets of downtown for shopping and delicious bites to eat.

25 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.

Christmas at the Farm

Travel to Victorian Christmas past at Billings Farm & Museum throughout December. Enjoy the farm decked out for the holiday season with special festive offerings during December weekends and daily from Saturday, December 21, 2024 – Sunday, January 5, 2025, 10:00 AM – 4:00 PM. (Closed December 24 & 25.)

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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.

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Woodstock Nordic Center

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.

*Don’t miss a new addition to Woodstock– Sip & Shop, for special sips and surprises from 5-7pm in the 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.

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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.