undefined Itinerary

Spend the morning exploring the charming shops and galleries in downtown Woodstock. From unique art pieces to handmade crafts, you'll find plenty of treasures to take home as souvenirs. Make sure to visit the Tinker Street Cinema, a local independent theater that screens a mix of classic and contemporary films.

Embrace the winter season with some outdoor activities. Head to Overlook Mountain Bikes and rent some snowshoes or cross-country skis. Explore the beautiful trails in the area and enjoy the peacefulness of the winter landscape. If you prefer something more adrenaline-pumping, try snowboarding or skiing at nearby Hunter Mountain.

After a day of outdoor adventure, warm up with a hearty meal at The Bear Cafe. Located in a historic mill, this restaurant offers a cozy atmosphere and a menu featuring locally sourced ingredients. Don't miss their signature Bear Burger made with grass-fed beef and topped with caramelized onions and Vermont cheddar.

Begin your day with a visit to the Woodstock Museum. Learn about the town's fascinating history, including its role in the 1969 Woodstock Festival. The museum showcases artifacts and memorabilia from the iconic event. Afterward, take a leisurely stroll along the Tannery Brook Waterfall Trail and enjoy the serene beauty of nature.

Explore the Ashokan Rail Trail, a scenic path that follows the route of the old Ulster and Delaware Railroad. Rent a bike from Overlook Mountain Bikes and pedal along the trail, taking in the picturesque views of the Ashokan Reservoir and surrounding mountains. Pack a picnic lunch to enjoy at one of the trailside picnic areas.

Treat yourself to a fine dining experience at the Red Onion. This upscale restaurant offers a menu inspired by farm-to-table cuisine, using locally sourced ingredients. Indulge in dishes like roasted duck breast or seared scallops, paired with a glass of wine from their extensive selection.

Immerse yourself in the natural beauty of Woodstock by visiting the Catskill Mountains. Take a scenic drive along Route 28 and stop at the Kaaterskill Falls, one of the tallest waterfalls in New York. Enjoy a short hike to the viewing platform and marvel at the cascading water surrounded by snow-covered trees.

After your outdoor adventure, warm up with a visit to the Woodstock Museum of Glass. Admire the stunning glass art pieces created by local artists and learn about the techniques used in glassblowing. You can even try your hand at creating your own glass artwork during a workshop.

End your day with a cozy dinner at the Bearsville Theater Complex. This unique venue combines a restaurant, bar, and live music venue. Enjoy a delicious meal while listening to live music performances by local and national artists. Check their schedule for upcoming shows and book your tickets in advance.

Start your day with a visit to the Woodstock Farm Sanctuary. Take a guided tour and meet rescued farm animals, including cows, pigs, chickens, and goats. Learn about their stories and the importance of animal welfare. Afterward, stop by Sunfrost Farms to grab some fresh fruits and vegetables for a healthy snack.

Explore the scenic beauty of Woodstock by taking a horse-drawn carriage ride. Enjoy a leisurely ride through the snow-covered streets and immerse yourself in the peaceful atmosphere. Afterward, visit the Woodstock Artists Cemetery, where you can pay homage to the famous artists and musicians buried there.

Indulge in a farm-to-table dining experience at The Pines. This restaurant focuses on using locally sourced ingredients to create delicious and innovative dishes. From homemade pasta to grilled meats, their menu offers a variety of options to satisfy your taste buds. End your evening with a glass of wine or a craft cocktail at the cozy bar.