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  • Christian Morris

Christmas In Woodstock - Top 5 Most Festive Things To Do

Coming to Woodstock in the winter? Come step into a living Hallmark Christmas movie.

A generally small town during most of the year suddenly turns into arguably the most festive city in the country. Between the snow, trees and cheery resident spirit Woodstock makes for the perfect stop in your perfect winter vacation. We've made a list of the top 5 most festive things to do in Woodstock in the winter. Make sure to take advantage of the unique seasonal activities this town has to offer!

5. Snowshoeing

Get your blood pumping with some snowshoeing in the woods of Mount Peg and Mount Tom. Woodstock has many expert-led tours to help you get the most out of your adventure while maintaining important safety measurements.

Your first stop should be Woodstock Nordic Center for snowshoe rentals and guides. Their vast range of trails caters to all levels of ability and has everything you need for a successful adventure. If you’re lucky, you might even be able to catch a snowshoe trek up to the Mount Tom Cabin for lunch!

Snowshoeing is a great activity whether you follow a tour guide or trek the trails on your own. Don’t forget to stop downtown for a hot chocolate to warm you up afterward!

4. Sledding

Looking for a family-friendly thrill in those cold winter months? Look no further than Ascutney Outdoors, with a 500-foot long sledding slope! Located only 30 minutes away from Woodstock village, it’s a no-brainer for making fun memories together. The path is groomed, guaranteeing the fastest ride down for you and your kids. Their brand-new tubing shuttle pulls you back up the hill, so you can spend less time hiking up and more time sledding!

If you’re wanting a more budget-friendly sledding day, we recommend the Quechee Sledding Hill! It’s only a 10 minute drive from Woodstock village and a local favorite. The hill used to operate as a ski resort and now provides the best sledding in the area. And the best part? It’s free! Make sure to bundle up and bring your own sleds for an afternoon of guaranteed laughter.

If you are looking for a little more excitement you may be interested in one of the many ski resorts in the area. Rental equipment is available and beginner friendly for those who are coming into town to try skiing for the first time.

3. Downtown Woodstock

Downtown Woodstock in winter

Downtown Woodstock has a picturesque charm that brings in thousands of tourists each season. Small business owners add a unique flair to the shops with plenty of local goods including maple syrup, handmade souvenirs, and specialty food items. Many visitors opt to rent a bike and cruise through the streets, stopping for a snack as they ride. Pleasant Street boasts a plethora of shops including Yankee Bookshop, Pleasant Street Books & Cards, Vermont Flannel Co, and Clover Gift Shop.

Looking for a tasty meal? Downtown has all the local favorites, including Mon Vert Cafe, Soulfully Good Cafe, and Abracadabra Coffee Co. Many visitors like to stroll along the downtown area, window shopping and sampling the delicious local food. You won’t want to miss the beautiful homes that line the streets. During fall and winter, they’re always decked out for the holidays!

2. Wagon Tour


Bundle up if you're interested in taking Woodstock by wagon. Woodstock has many wagon tours that will take you siteseeing through the town.

The Woodstock Inn and Resort has a major perk for lodging with them: horse-drawn carriage rides! Ride along in a traditional carriage and tour the beautiful town dressed up for the holidays. The tours leave every half hour from the inn. You’ll feel like you’re in a storybook on this romantic ride.

Kedron Valley Stables also offers carriage ride tours that ensure 45 minutes of a winter wonderland. Taking you through the gorgeous countryside and wooded sections of Woodstock, you are able to see a part of the town you most likely wouldn’t on your own! Cozy up with their provided blankets for the most magical evening activity.

1. Wassail Weekend

Woodstock Wassail Parade

Wassail Weekend is the best time of year to visit Woodstock! Hosted in early December, the town transforms into a holiday wonderland. Wassailing is an ancient English custom that began with a feast and spiced ale. Families passed around the drink and said “Wass Hael”, meaning “Be Well”.

Woodstock carries on the wassailing tradition with fun activities including an equestrian parade, a town scavenger hunt, and a wassail feast! You’ll devour traditional items including potato soup, cornish game hen, Atlantic black cod, sticky toffee pudding, and English trifle. With twinkling lights, historic homes, sleigh bells, and decorated farms, you won’t want to miss this festive holiday weekend.

Arguably the pinnacle of Wassail Weekend is the Saturday afternoon parade. The parade draws in the majority of the town as well as visiting guests. Taking after long standing traditions the Wassail parade floats consist of mostly horses and wooden wagons. The parade is in no rush taking its time through Woodstock streets and citizens don’t seem to mind either. Everyone seems to be enjoying the moment of holiday cheer and a comforting sense of community.

Bonus Activity:

Check out the Taftsville Covered Bridge just outside of downtown Woodstock. Covered bridges have become a staple tourism attraction for the state of Vermont. The Taftsville covered bridge crosses the Ottauquechee River an impressive 89 feet into a small subsection of Woodstock called Taftsville.

This bridge serves as a unique experience being both picture friendly and excited to drive through. Because it is not as frequently visited as other activities we listed, feel free to take your time and enjoy the wooded scenery.

You can find directions to the Taftsville bridge here.

You’ll find on your trip that there is plenty more to do while visiting Woodstock. With a rich history reaching back to early settlers, this town is rooted in community traditions. Whatever you end up doing during your stay in Woodstock, just make sure to match the festive energy this little town gives off to each of its guests.

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