The Best Activities For a Winter Trip to Woodstock, NY

The Relax in Woodstock House in Winter

Winter in Woodstock is a magical time of year. With the busy seasons of the summer and fall in the rearview, the area, retires for the winter into an even quieter and more cozy escape. Located just 20 minutes off of the New York State Thruway, Woodstock is incredibly accessible in the winter time no matter what the weather presents. It provides the perfect setting for a weekend of skiing, snowshoeing, hiking, or just bundling up in a cozy country home to catch up on sleep, work and life. In this blog post, we'll explore the best things to do in winter in Woodstock, New York.


Hit the slopes for some skiing

If you're a winter sports enthusiast, then you won't want to miss out on the opportunity to hit the slopes at Hunter Mountain, Belleayre, . These popular ski resorts in the Catskills and Berkshires are short drives from Woodstock and offer a variety of runs for skiers and snowboarders of all levels. If you’re looking for a great family mountain with easy, terrain, short runs and a small mountain feel, Bellayre is the right choice for you. Located approximately 30 miles west of Woodstock, it’s approximately a 40 minute drive you can easily wake up and be on the mountain for first runs.

If you’d like, a little bit more challenging terrain and a bigger mountain feel we suggest going to Hunter Mountain. Hunter has 66 trails and even has back bowls! Located 30 miles north of Woodstock approximately a 40 minute drive. If you’re a West Coast skier with an Epic Pass, Hunter is included!

Click here to read more detail on the ski resorts we recommend.

Take a scenic drive

Winter in Woodstock is a picturesque season, with snow-capped mountains and frozen streams. Taking a scenic drive through the Catskill Mountains is a great way to take in the winter beauty. Some of the popular routes include Route 28, which takes you through scenic towns like Phoenicia and Pine Hill, and Route 214, which winds through the mountains and offers breathtaking views.

Warm up with a hot drink

After a day of exploring Woodstock, warm up with a hot drink at one of the town's cozy cafes. The Garden Café is a popular spot that serves delicious coffee and tea, as well as baked goods and sandwiches. You can also check out Bread Alone Bakery for some of the best bread, pastries, and coffee in the area.

Stroll the town and eat wherever you want

Of the most underrated parts of winter time in Woodstock is being able to eat at the endless amounts of top shelf restaurants without the need for reservations or thinking ahead. During the summer months, it can be quite difficult to get a reservation or a spontaneous walk up at places like Sylvia or Cucina. In the winter this changes and it’s a great time to visit these restaurants in a more relaxed setting.

The town is much quieter in the winter and if you get a warm enough day, it’s quite charming to walk through town during this time of year the center of town. During the holiday season, there’s always great decorations to view and take photos of.

Go sledding at The Comeau Property

Take a ride over to The Comeau Property and join in the fun as kids and parents alike sled down this oversized town favorite sledding site. After you turn into the property from tinker Street, take the road to the end and park in the parking lot (upper parking lot). Walk towards the trailhead sign and then take the path straight ahead until you see a bunch of people having a blast sledding down the hill. Walk to town after you’re done sledding and grab a coffee or a hot cocoa.

Order in!

On those frigid nights, plan ahead and order in some of the best food you can get from Bistro-to-go on Route 28 with everything from sandwiches and salads to entrées and sides of the day. Most restaurants offer take-out so head on over to our Places to Eat page to find your ideal comfort food for a night in.

Plan an executive retreat or team outing

Winter is a great time to do this as all of the activities are still in play, but the pricing is much more favorable. Bring your executive team into the mountains and give them access to all the winter activities and great food that the area has to offer.


In conclusion, Woodstock, New York, is a winter wonderland with plenty of activities to keep you entertained. From skiing to ice skating, there's something for everyone. So, grab your warmest coat, put on your boots, and head to Woodstock for an unforgettable winter getaway.

 

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