12 Amazing Things to Do in Woodstock Vermont in Winter 2024

Woodstock, Vermont, has a special place in my heart. It’s a town that captures the essence of New England charm in a way that’s hard to find anywhere else. You can do So many amazing things to do in Woodstock in winter.

Woodstock transforms into a dreamy winter destination from the first snowfall to the last. I’ve wandered its snowy streets, enjoyed its festive spirit, and indulged in the warmth of its community. Once visited, it’s a place that becomes a must-return on your travel list.

In this guide, I’m going to share with you 12 amazing winter activities in Woodstock. Whether it’s the thrill of skiing, the charm of a winter festival, or the simple joy of a cozy evening in a historic town, Woodstock offers a range of experiences that make for an unforgettable winter getaway.

So, let’s dive in and discover why Woodstock is the perfect winter destination, with activities beyond the ordinary and into the heart of Vermont’s winter wonderland.

Is Woodstock Vermont Worth Visiting?

If you’re asking whether Woodstock is worth a visit in winter, my answer is a resounding yes! Having spent countless winters here, I can confidently say that Woodstock is more than just a destination; it’s an experience that stays with you.

As my trip to Vermont was a memorial trip, it get to see such amazing places in Vermont and I have enjoyed my trip that’s why I kept exploring more and more. I have explored Stowe, Burlington, and then I decided to visit Woodstock also so I don’t miss any part in Vermont.

Woodstock is a town that feels draped in a blanket of snow, with twinkling lights lining the streets and the air filled with the scent of woodsmoke. It’s where you can slow down, breathe in the crisp winter air, and enjoy simple pleasures.

Woodstock apart has a unique blend of outdoor adventure, cultural richness, and small-town charm. Whether exploring its historic streets, participating in winter festivities, or enjoying its natural beauty, Woodstock offers an enriching and heartwarming winter experience.

Amazing Things to Do in Woodstock in Winter

When winter blankets Woodstock in snow, it brings a new world of activities and experiences. I mean, it’s not just about enjoying the snow, but immersing yourself in a season that turns a charming town into a winter fairytale. From unique festivals to outdoor adventures, Woodstock offers a variety of ways to enjoy its winter wonder.

Let’s dive into some of the most amazing things to do in Woodstock during the winter months:

1. Attend the Wassail Weekend Event in December

Wassail Weekend is a winter season highlight of the Woodstock. It happens on the second weekend in December. The town wraps itself in festive delight, inviting everyone to join in a celebration rich in tradition and community spirit.

The weekend starts with activities like the Wassail Scavenger Hunt, exploring old-time traditions at Billings Farm & Museum, carriage rides through the village, and a variety of musical and literary events.

The heart of the celebration features the iconic Wassail Parade, a lively artisan and food market, ornament making, a craft fair, and various performances and readings throughout the day. As evening falls, the town green hosts a Wassail bar, a luminary and tree lighting, a bonfire, and Christmas caroling.

The weekend concludes with Victorian Christmas activities at Billings Farm & Museum, including candle dipping and horse-drawn sleigh rides, ice skating with Santa, puppet shows, and the Messiah Sing event.

2. Experience Woodstock’s Snow Sculpture Festival

In February, Woodstock turns into an outdoor art studio. It’s about the Vermont Flurry, the town’s snow sculpture festival. Picture this: artists carved huge blocks of snow into incredible shapes on the Village Green. It’s a real treat to watch.

This event is notable because it’s the only one in Vermont. You’ll see all sorts of sculptures, from funny to fancy. And you get to pick your favorite by voting in the “People’s Choice” award.

The whole thing feels like a big, friendly competition. On the last day, they announce the winner, who gets to go to a national contest. Walking around these snow sculptures and talking to artists is a fun way to spend a day in Woodstock.

3. Maple Madness

Woodstock’s Maple Open House Weekend is another must-experience event. It is typically held in late March. You can taste different kinds of maple syrup – from the classic to maple cream, butter, and even unique blends like maple horseradish mustard.

Local sugar makers, the Luce family, opened their farm for this event. Using traditional methods, you can learn how maple sap is collected and boiled into syrup.

If you had a chance to experience this sweet event, do check some local Vermont cheeses, and enjoy samples from various local food producers. This weekend celebrates Vermont’s maple heritage and offers a sweet peek into the local culture and craftsmanship. It’s a perfect blend of education, tasting, and experiencing the local way of life.

4. Visit Billings Farm & Museum

Visiting Billings Farm & Museum in Woodstock during winter is a must-do. Open each weekend, this place takes you back to a 19th-century farm. You can meet and learn about different farm animals in their cozy barns. The farm offers a unique program, ‘Winter on the Farm,’ which shows what farm life was like back in 1890.

There are activities for the whole family, like crafting a dove of peace or joining a story walk. The farm also organizes special events on Martin Luther King Jr. Day weekend, including sleigh rides and historical film screenings.

If you’re into crafts, they have workshops like making felted soap using local products. And for the foodies, there are cooking workshops where you can learn to make dishes like sauerkraut and kimchi.

To top it off, there is a unique event that I have never heard or imagined, “torchlight snowshoe event”. Imagine walking the farm’s trail by torchlight in the evening, warming up later with s’mores and hot drinks by a fire pit.

5. Skiing or Snowboarding at Saskadena Six and Killington

Saskadena Six Ski Area is Known for its family-friendly and beginner-friendly slopes, Saskadena Six, formerly Suicide Six, is an excellent place for those starting out or looking to enjoy a relaxed skiing experience.

With groomed trails and a cozy alpine lodge complete with an indoor/outdoor fireplace, it’s a welcoming spot for a day on the slopes. Rentals and a restaurant are conveniently located steps from the skiing area​​.

Killington Ski Resort is one of the top ski destinations on the East Coast. It boasts 1,509 skiable acres across six mountains, with a diverse range of terrain suitable for all skill levels.

Non-skiers can also enjoy snowmobile tours, the Beast Coaster, sleigh rides, and snowshoe tours. The resort averages 250 inches of natural snowfall annually, supported by an extensive snowmaking system.

Killington Village offers a variety of restaurants, bars, and après-ski options, making it a full-fledged winter resort experience​​​​​​.

6. Snowshoeing or Cross-Country Skiing

Winter in Woodstock offers an exceptional opportunity for snowshoeing and cross-country skiing. The area boasts an extensive network of trails perfect for outdoor activities in Woodstock.

Majestic Trails is my first recommendation if you are into skiing. Woodstock transforms into a winter wonderland with dozens of natural and groomed trails. These trails are ideal for both skate skiing and classic cross-country skiing, providing a serene way to experience the snowy landscape.

Second one is “The Tubbs Snowshoes & Fischer Nordic Adventure Center”. This center features over 30 km of groomed trails throughout Mount Peg and Mount Tom. The trails cater to various skill levels, making it a great place for both beginners and seasoned skiers.

If you’re new to these activities or didn’t bring your gear, don’t worry. You can rent equipment from several local outfitters. Hiring a snowshoe guide or taking a Nordic ski lesson is an excellent option for those looking to improve their skills or explore hidden gems.

7. Fat Bike Riding

Fat tire biking is a fun winter activity in Woodstock. These bikes, with their wide tires, are perfect for snowy trails. They let you float over snow where regular bikes would sink. It’s a great workout too, challenging your balance and core strength.

The Woodstock Inn’s Nordic Center offers fat tire biking on 25 km of groomed trails on Mt. Peg. It’s a unique way to enjoy the outdoors, especially when there isn’t enough snow for cross-country skiing. These bikes handle various terrains, from snowy trails to muddy paths.

Open from mid-December to early April, it’s a fresh way to explore Woodstock’s winter landscape, combining exercise with the beauty of nature​​.

8. Ice Skating

Ice skating is a classic winter activity, and in Woodstock, you have both indoor and outdoor options. At the Union Arena, you can enjoy indoor skating with public skate times available, including options for pick-up hockey and skate rentals.

For a more traditional outdoor experience, head to Vail Field, just south of the town green. Transformed into an outdoor rink in the winter, it’s a place where you can skate under the open sky. Whether you’re into figure skating, ice hockey, or just learning to skate, Vail Field is ideal.

And the best part is, It’s a community-supported space, free and open to all, and they even have skates available for use, donated by the community​​.

9. Snowmobile Tours in Woodstock

The Woodstock area boasts hundreds of miles of meticulously groomed VAST Trails, making it a paradise for snowmobile enthusiasts.

To embark on this winter adventure, you must join a local club and register your snowmobile with the Vermont Association of Snow Travelers (VAST) is a well known club for its commitment to providing the best trails in the Northeast.

Whether you’re a seasoned snowmobiler or trying it for the first time, the trails in Woodstock offer a diverse range of experiences. From tranquil forest paths to more challenging routes, every turn brings a new and stunning vista. The trails are well-maintained and offer safe yet thrilling rides through the winter landscape.

If you don’t own a snowmobile, don’t worry. There are several rental and tour companies in the area that can equip you with everything you need for a memorable ride. Also, if you were born after July 1, 1983, you must complete a safety course before hitting the trails.

Once all set, you’re free to explore the vast network of trails throughout the state, ensuring an unforgettable snowmobiling experience in the heart of Vermont​​.

10. Tubing at Killington

Consider tubing at Killington Tubing Park for a delightful winter activity that offers fun for the entire family. Located at the Clubhouse on East Mountain Road, right across from the Killington Grand Resort Hotel, the park features multiple tubing lanes and a convenient lift service.

Tubing sessions at Killington are an hour long and begin every hour from when the park opens. The park’s lift service efficiently takes you to the top for another thrilling slide down the hill, allowing you to maximise your tubing session. The park caters to all ages, provided participants are at least 36 inches tall.

The pricing is also accommodating, with rates for a single session ranging from $15.00 for Vermont residents with a valid ID to $59.00 for a season pass. For those under 18 years, a single session costs $20.00; for adults 19 and older, it’s $25.00. Note that there is an additional $5.00 charge for youth and adult tubers during peak days.

Group bookings offer a discount, with groups of 12 or more saving 20% when pre-purchasing tickets. This makes it an excellent option for larger gatherings or family reunions looking for a fun and memorable winter activity.

11. Indoor Rock Climbing at Green Mountain Rock Climbing Center

For a unique and adventurous indoor activity in Woodstock, Vermont, head to the Green Mountain Rock Climbing Center (GMRCC). Located at 223 Woodstock Ave in Rutland, this center is a haven for climbing enthusiasts and novices.

With a 4.5 rating and recognition as one of Rutland’s top fun and games centers, GMRCC offers an engaging and supportive atmosphere for climbers of all levels.

The center, renowned for its high-quality equipment and expert guidance, caters to beginners and advanced climbers. Personalized experiences are a highlight here, with opportunities to challenge yourself under the guidance of skilled instructors like Steve, known for his patience and extensive outdoor experience.

The center frequently updates its facilities, including adding a boulder room, ensuring a fresh and exciting experience for repeat visitors.

12. Shopping in Woodstock, Vermont

Woodstock, Vermont, is a shopper’s paradise, especially for those who appreciate the charm and quality of local artisans and boutique stores. The village and its surrounding area are pedestrian-friendly, making shopping a leisurely and enjoyable experience. Here are some highlights:

The Yankee Bookshop: It was established in 1935, this bookshop offers a big-city selection in a small-town setting, featuring a wide range of books, vinyl records, stationery, and bookish gifts. It’s known for its friendly and knowledgeable staff, ready to help you find your next favorite read.

Billings Farm & Museum: If you are in Vermont, then you must visit to this working dairy farm and museum. It’s a unique shopping experience where you can learn about farm life and find products directly from the farm.

Ferro Jewelers: It is Known for its vast selection of Vermont charms, many handmade and inspired by local imagery, Ferro Jewelers is a go-to destination for exquisite jewelry.

Artisan Galleries: Woodstock is home to galleries owned and operated by local artisans, where you can meet the artists and explore their creations.

Elevation Clothing: Providing stylish clothing and accessories for an active lifestyle, this store caters to both men and women, offering quality apparel for outdoor adventures or casual wear.

Handcrafted Pottery and Homeware: The town boasts shops where you can discover handcrafted and modern homeware, engage with master potters, and even participate in workshops to create your artisan souvenirs.

Things to do In Woodstock Conclusion

Woodstock, Vermont, is a winter wonderland that offers many activities for visitors of all ages and interests. From the thrill of snowmobiling through picturesque trails and the joy of tubing down the slopes at Killington, to the challenge of indoor rock climbing and the delight of unique shopping experiences, Woodstock truly has something for everyone.

Its blend of outdoor adventures, cultural experiences, and the warmth of a small-town atmosphere make it a must-visit destination. Whether seeking adventure, relaxation, or a taste of Vermont’s charm, Woodstock in winter is an experience you won’t forget.

FAQs: Things to Do in Woodstock, Vermont