Things to Do in Woodstock, New York

Woodstock, New York, is a charming and historic town in the Catskill Mountains. Known for its bohemian spirit and artistic community, Woodstock has long been a haven for artists, musicians, and free thinkers. Its unique blend of natural beauty and the cultural richness continues to draw visitors worldwide.

The town is surrounded by scenic hiking trails, waterfalls, and lakes, making it a popular destination for outdoor enthusiasts. At the same time, Woodstock is home to a thriving arts scene, with numerous galleries, theaters, and music venues showcasing local and international talent. Woodstock offers something for everyone, whether you’re looking for adventure, inspiration, or a peaceful getaway.

Things to Do in Woodstock, New York

Opus 40

Opus 40 is a fantastic artwork that has inspired thousands of people across the country. Artist Harvey Fite created this large-scale environmental sculptural installation.

The sculpture is located near the town of Saugerties, New York. It is an homage to the Hudson River region and the local arts scene.

Three buildings make up the sculpture, including a large wood and stone home and a blacksmith shop. It is an impressive structure that is open to the public. You can walk around the sculpture and visit the museum.

Best places to visit in Woodstock - Opus 40
Best places to visit in Woodstock – Opus 40

The park is also home to several hiking trails. You can take in the views of the Catskill Mountains. In addition, some ponds and trees help to create the perfect atmosphere.

The museum at Opus 40 features an outdoor sculpture exhibition, and there are plenty of events for the whole family. On Friday nights, the park hosts local musicians and food trucks.

Overlook Mountain Trailhead

Overlook Mountain is a popular hiking destination in the Catskills region of New York. It is located just a two-hour drive from New York City.

The Overlook Mountain Trailhead is a moderately difficult trail that takes you to the cliffs and ruins of a former Catskills hotel. While the hike is fun for adults, kids will find the trail dull and tedious.

Places to go in Woodstock - Overlook Mountain
Places to go in Woodstock – Overlook Mountain

Overlook Mountain is the centerpiece of the Overlook Mountain Wild Forest area of Catskill Park. It covers 590 acres.

There is a lot to see and do in Woodstock, NY, a town awash with shops, art galleries, restaurants, and boutiques. The city is also home to a variety of overnight accommodations. You can choose from quaint inns to funky Air BnBs.

Phoenicia Diner

The Phoenicia Diner in Woodstock, New York, has the quintessential diner feel. It’s set in a small town on a secluded state highway. Yet, despite its rural setting, it’s easy to access by bus and car.

It’s a great place to eat, drink and enjoy the scenery. You’ll find all-day breakfast and brunch menus with thick specialty shakes. There’s also a lounge serving local-inspired cocktails. In addition, they’ll soon add a food truck to the property.

What to do in Woodstock, New York - Phoenicia Diner
What to do in Woodstock, New York – Phoenicia Diner

If you’re in the mood for something more elevated, try Graham & Co. This restaurant is located on three acres. For dinner, you can enjoy a variety of entrees and desserts. They also have 20 rooms on the property.

Another local favorite is Dixon Roadside. This retro-cool diner offers a modern take on classic 1950s dine-and-go restaurants. It features an authentic mid-century vibe near the Bearsville Theater in Woodstock.

Overlook Mountain House ruins

The Overlook Mountain House ruins are located in the Catskills. It is a popular hiking trail.

The ruins have three parts: the main hall, the side rooms, and the main staircase. This building is now part of the Catskill Forest Preserve. While the ruins are not finished, they are not yet abandoned. On the contrary, the structure is slowly reclaimed as the forest grows.

Best tourist attractions in Woodstock - Overlook Mountain House Ruins
Best tourist attractions in Woodstock – Overlook Mountain House Ruins.

One of the best ways to get to the ruins is to take the Overlook Spur Trail. Follow the old carriage road and get a great view of the mountain. There is also a fire tower at the top of the mountain. In addition, you can see 360-degree views of the surrounding area.

Another notable feature of the ruins is the fountain. This fountain was initially filled with water but was not used much, hence its demise.

Ashokan Reservoir

If you are looking for a place to go in the Hudson Valley to experience the natural beauty of the Catskill Mountains, you may want to check out Ashokan Reservoir in Woodstock, New York. The reservoir provides about 40% of New York City’s drinking water.

It is the largest reservoir in the NYC area at over 8,000 square acres. Located in Ulster County, the reservoir was built in the early 1900s. The New York City Department of Environmental Protection owns a large part of the reservoir.

Places to visit in Woodstock - Ashokan Reservoir
Places to visit in Woodstock – Ashokan Reservoir

You will find an array of wildlife in the Ashokan Reservoir, including the American Bald Eagle, Belted Kingfishers, and Great Blue Herons. There are also several trophy fish to be caught.

While the reservoir is not a great place to swim, you can enjoy various recreational activities. For example, you can hike or bike along the Ashokan Rail Trail, an 11.5-mile multi-use trail. This trail is flat and suitable for hiking, running, cycling, and dog walking.

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