Things to Do in Woodstock, New York

This is one of the three most-visited spots in the Catskill Forest Preserve. The round trip is under 5 miles and passes the ruins of the old Overlook Mountain House before reaching a historic fire tower. From the top you see the Hudson Valley and the central Catskills.

★ Good to know The trailhead lot is about 2 miles up Meads Mountain Road from the Village Green; go early on weekends, and stay out of the hotel ruins.

Five artists founded WAAM in 1919, and it’s still the town’s art anchor on Tinker Street. The permanent collection includes Milton Avery, George Bellows, Philip Guston and Yasuo Kuniyoshi, all tied to the Woodstock colony. Changing shows fill the galleries through the year.

★ Good to know The galleries open Wednesday through Sunday afternoons in summer; hours shift in the off-season, so check before you go.

Poet Hervey White built a “music chapel” in the woods in 1916, and it’s now home to the oldest ongoing summer chamber music festival in the country. The hand-built hall is on the National Register of Historic Places. The program mixes classical with jazz, folk and contemporary music.

★ Good to know The season runs June to September, and Maverick Family Saturdays are free for kids and adults.

Founded in 1902 and 1903, Byrdcliffe is one of the oldest Arts and Crafts colonies in the country. Its 350 acres on the lower slopes of Mount Guardian are on the National Register, and it still hosts local and visiting artists. Voice Theatre is in residence at the colony’s Byrdcliffe Theater.

★ Good to know The Woodstock Byrdcliffe Guild runs exhibitions and the Fleur de Lis craft gallery; check its calendar before you drive up.

Sculptor Harvey Fite spent decades shaping this 6.5-acre earthwork out of an old bluestone quarry, about four miles from the center of Woodstock. It sits inside a 63-acre sculpture park with quarry trails, a gallery and the Quarryman’s Museum. You can walk up, down and around the stone ramps and pools.

★ Good to know Allow at least an hour; it closes for the season in early November, and tickets can sell out on fall foliage weekends.

Tinker Street is Woodstock’s main drag, running past the Village Green, the town hall and WAAM, with galleries and shops along the way. It’s the easiest place to feel the town’s arts-colony history on foot. The Artists’ Cemetery on nearby Rock City Road holds many of the colony’s artists.

★ Good to know Park once and walk; the Green is also where the Overlook directions start.

This 11.5-mile path follows the old Ulster and Delaware Railroad along the north shore of the Ashokan Reservoir, just south of Woodstock. Its crushed-stone surface is flat and wheelchair-accessible, and the Woodstock Dike trailhead in West Hurley has wide reservoir and mountain views. It opened fully in 2019.

★ Good to know For the best views in the least distance, walk the dikes near the West Hurley trailhead.

Founded in 2000, this festival screens independent films and is Oscar-qualifying in three short-film categories. It’s the town’s big fall event, and it fits neatly into a foliage weekend.

★ Good to know It usually runs from late September into early October; buy passes early.