Upstate New York is mostly recognized for its diverse scenic landscapes, which offer endless opportunities to unplug. Woodstock, in particular, uniquely blends nature and art, offering an incredible variety of activities. It’s known for its relaxed pace of life, breathtaking vistas, and welcoming atmosphere. Discover the best things to do, from outdoor activities to art and dining experiences.
Drive the Scenic New York State Route 212
New York State Route 212 winds through Ulster County, connecting Saugerties and Woodstock. The two-lane roadway is known for its gorgeous views of the Hudson Valley. You’ll pass through a range of breathtaking natural features, including Cooper Lake, the Catskills’ largest natural lake. The lake, which is Kingston’s main water supply, is a popular outdoor area with scenic nature trails.
Explore the Scenic Woodstock Waterfall Park
If you are seeking a serene retreat with views near downtown, explore Woodstock Waterfall Park, right off of town’s Main Street. The tiny park along Tannery Brook Road features a waterfall as its main highlight. The waterfall is small, but watching it cascade into a tranquil pool is magical. The beautiful scenery and peaceful setting make a perfect backdrop for taking photos.
Stay at the Woodstock Inn and Access Millstream
There are fantastic accommodation options in the Woodstock area, but the Woodstock Inn is unmatched. The bed and breakfast enjoys a scenic location on the Millstream, a beautiful swimming hole near Woodstock’s downtown. The hole was once a popular outdoor area but is now closed to the public due to overcrowding and irresponsible use; only guests staying at the inn are allowed access. The inn’s comfortable rooms are a perfect spot to unplug after a long day of enjoying the great outdoors.
Hike the Overlook Mountain
Overlook Mountain is one of the Catskill Forest Preserve’s most summited peaks. The hike offers many incredible features, including a historic fire tower with 360-degree views of the Catskills and Hudson River. You’ll also discover the ruins of the Overlook Mountain House, an abandoned high-elevation hotel that was one of the leading factors in the area’s tourism boom in the 1800s.
Go Shopping on Tinker Street
Woodstock is not all about spectacular natural surroundings. Stroll along the vibrant Tinker Street for a unique shopping experience. As the town’s Main Street, it teems with unique stores—from boutiques to bakeries and gift shops—and offers great entertainment options, including live music venues like Tinker Street Tavern.
Go Hiking in Sloan Gorge Preserve
Sloan Gorge Preserve is an 88-acre outdoor area with diverse features, including hardwood and coniferous forests, a seasonal stream, and more. It is known for its one-mile interpretive geology loop trail, which provides insight into the area’s rich geological history. The preserve is also a wildlife haven that is family-friendly and popular with educational tours.
Hike the Mink Hollow Trail to Twin Mountain
Hiking the Mink Hollow Trail to Twin Mountain in the Indian Head Mountain Wilderness is one of the best things you can do in Woodstock. The mountain is among the 35 peaks that tower over 3,500 feet and offers some of the most sweeping views of the region. The hike meanders through beautiful natural features but is challenging and includes steep sections and loose rocks.
Discover the Great Outdoors in Echo Lake
Echo Lake is one of the most beautiful outdoor areas near Woodstock and can be reached via the Overlook Trail. It is part of the scenic Indian Head Wilderness Area, where the headwaters of the Sawkill River originate. From fishing to camping and hiking, this area offers multiple ways to connect with nature.
Explore the Ashokan Rail Trail (ART)
Ashokan Rail Trail is one of the most scenic recreational routes you can explore in Woodstock. It follows a historic railroad route along the Ashokan Reservoir’s beautiful shore. You can enjoy various activities here, including hiking and mountain biking, while taking in the impressive vistas of the area’s diverse natural surroundings. The trail is considered one of the top outdoor areas in the Hudson Valley and offers an easy escape from nearby cities, including Jersey City.
Visit George Bellows’ House
George Bellows was one of the greatest artists in the US. Inspired by the area’s breathtaking natural surroundings, he spent part of every year between 1920 and 1924 in Woodstock. He created over 100 paintings and described this sleepy village as the “perfect combination of nature and neighborhood.” His home, now a historic site, was the town’s cultural center during his time there. You can visit his former home to learn about his life.
Visit Garden Café Woodstock for Fresh Vegan Food
If you are a vegan, don’t leave Woodstock without trying fresh, organic meals at Garden Café, right in the heart of the Hudson Valley. It has an extensive menu with numerous vegan and vegetarian options, from tofu dishes to garden bowls. The outdoor seating area is impressive, especially during warmer months.
Catch a Live Theater Performance at Woodstock Playhouse
Established in 1938, Woodstock Playhouse has been a significant part of American theater and music history. It remains a local haven for theater and music enthusiasts, hosting various events and productions—from concerts and films to festivals. It can accommodate up to 321 people and features two impressive galleries.
The Mud Club is a Perfect Spot to Recharge
Whether you are just beginning or in the middle of your outdoor adventure in the Hudson Valley, the Mud Club makes a quick stop for some eats. Dating back to 2017, the restaurant is known for its wood-fired bagels, but it also serves organic coffee, pizza, and a variety of sandwiches and pastries. The charming setting feels like a fairy tale, with everything served fresh.
Explore Local Art and Cultural Heritage at Woodstock Artists Association & Museum
Admire art at the Woodstock Artists Association & Museum, which, since 1919, has showcased some of the finest artworks in the Catskills. You’ll experience numerous exhibitions in its impressive galleries, ranging from historic to modern art.
Enjoy a Tranquil Nature Stroll in The Comeau Property
Nestled near the town center, Comeau Property is a 76-acre nature preserve with great outdoor opportunities. It is perfect for a relaxing stroll among woods, meadows, and the Sawmill Stream. It is also popular among birdwatchers, and you can bring your furry friend along for the experience.
