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Among Woodstock's claims to fame are its ties to the famous Woodstock concert in 1969, although the event was actually held about an hour away in the town of Bethel. The Catskill Mountains region, where Woodstock is located, also was the inspiration for Washington Irving’s story about Rip Van Winkle, who took his lengthy snooze near the town of Catskill.

Woodstock is known as a great jumping-off point for exploring the Catskill Forest Preserve, particularly in autumn, when fall foliage colors light up the mountainsides. In fact, Woodstock is situated in the heart of the preserve, which is a state park spread across some 286,000 acres. There are more than 30 peaks and ridges with elevations beyond 3,000 feet, and most of them have walking trails for those looking to bask in the autumn splendor. A fall weekend itinerary can include lots of leap-peeping along with other outdoor and indoor activities.

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Mountains Galore Make Great Leaf-Peeping Opportunities

Overlook Mountain is a prime hiking spot in Woodstock for local people as well as visitors. The two-mile Overlook Mountain Spur Trail takes hikers past a fire tower and the ruins of an old hotel, the Overlook Mountain House. Two shorter trails are available, the Meads Meadow Trail and the Overloop Trail. The Overlook spur takes hikers to the top of Overlook Mountain along a former carriage road, offering prime fall foliage views.

For a captivating stop along the way, visit the Karma Triyana Dharmachakra Buddhist monastery, which is perched on the mountain overlooking the town of Woodstock. The monastery provides guided tours on weekends, and meditations and classes are offered to the public. Visitors are welcome to walk through the monastery's public areas and are asked to be respectful, with appropriate dress and a quiet presence.

Related: 10 Perfect Summertime Destinations In The Catskills

Another excellent choice for seeing fall foliage is the Kaaterskill Wild Forest and Kaaterskill Falls, a 260-foot waterfall in the nearby town of Hunter. The hike to Kaaterskill Falls is 1.4 miles roundtrip, and hikers are asked to remain only on the marked path due to the slippery rocks at the top of the falls. Peeks of the Hudson River Valley can be seen from the falls. This area is a top sightseeing attraction and is often crowded.

The Slide Mountain Wilderness is an expanse of 47,500 acres accessible through the town of Phoenicia, and is the largest wilderness area in the Catskill Forest Preserve. It sports an extensive trail network and offers excellent fall foliage views. This wilderness area is home to popular fishing opportunities, including the Esopus Creek and the east and west branches of the Neversink River. Anglers fish for brook trout, rainbow trout, and sculpin.

Indian Head Wilderness Area is another section of the state forest preserve, and it covers nearly 11,000 acres in four towns, including Woodstock. The hiking is more difficult here, with its rugged topography. Several trails are open to the public, and camping is offered, too.

Access to the whole of the state forest preserve is free.

Charming Downtown Woodstock Is A Big Tourist Draw

A traveler to Woodstock can't miss colorful Tinker Street, with its galleries, shops, restaurants, and historical sites such as the 19th-century Woodstock Reformed Church. Musical acts often perform on the village green, and many eateries offer outdoor dining. A lively flea market is held on weekends, where visitors can browse vintage clothing and jewelry, plus fresh, locally grown produce and more. From May through mid-October, the Woodstock Farm Festival draws area farmers selling everything from fresh eggs to prepared foods.

Known as an art colony from its earliest days, Woodstock is home to the Woodstock Guild and the Byrdcliffe Colony, a 350-acre art and performance center that offers art exhibits and classes, theater, dance, and concert events, and the Fleur de Lis Gallery, showing the works of some 60 artists. Byrdcliffe, founded by artists in 1902, is listed on the National Register of Historic Places. The guild’s permanent collection features 200 examples of arts and crafts, furniture, and decorative arts.

Fall season visitors to the Woodstock area also can see live theater at Performing Arts of Woodstock, a year-round organization that stages new and established plays.

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And for those visitors to Woodstock, the village, who want to know more about Woodstock, the concert, there's the nearby Bethel Woods Center for the Arts, an organization devoted to the iconic 1969 event. Located in Bethel, the museum's main gallery features “The Story of Woodstock and the 60s,” a permanent exhibit with 20 films, 164 artifacts, hundreds of photographic murals, and several interactive productions all focused on the three-day music festival. Tickets reserved online cost $17 for adults and $15 for seniors.

Easy Access To Woodstock By Public Transport Or Car

Located roughly two hours north of New York City, Woodstock is accessible by bus, train, and car.

  • By train: From New York Penn Station, travel to Rhinecliff station, then take a taxi to Woodstock.
  • By bus: From Port Authority Bus Terminal in New York, Trailways offers direct service to Woodstock's downtown.
  • By car: Take Interstate-87 to exit 19 and follow signs to the center of Woodstock.