The Best Activities For a Fall Trip to Woodstock, NY
Mill Hill Rd in Woodstock with Overlook Mountain in the background.
As the leaves change and the air turns crisp, Woodstock, New York, comes alive with a myriad of fall activities. Located in the Catskill Mountains, this picturesque town is a popular destination for leaf peepers, outdoor enthusiasts, and art lovers alike. Here are some of the best things to do in Woodstock in the fall.
Enjoy the Fall Foliage on a Hike
The Catskill Mountains are famous for their coloraful fall foliage, and there's no better way to experience it than on foot. Woodstock has several trails that offer stunning views of the changing leaves, including the Overlook Mountain Trail, which features a fire tower with panoramic views of the Hudson Valley, and the Kaaterskill Falls Trail, which leads to one of the highest waterfalls in New York State.
If you are a beginner and you’re just looking for an east stroll in the Catskill’s beautiful nature landscapes, we suggest looking at the Onteora Lake Trail or the Ashokan Rail Trail for a beautiful view of the Ashokan Resorvoir. These two trails are very close to Woodstock and offer a relaxing walk or a walk for exercise while taking in great views in nature.
If you are more serious about hiking, we suggest using Alltrails to map out your hikes. The information on AllTrails for the Catskill region is very reliable and you’ll find some of the best tips and tricks regarding optimal time of day, hazards and parking.
Explore the Art Scene & Local Markets
Woodstock has a rich history as an artist colony, and fall is a great time to explore the town's galleries and art spaces. The Woodstock Art Colony was founded in 1902, and the legacy of the artists who flocked here in the early 20th century can be seen in the town's many galleries and museums. The Woodstock Artists Association & Museum is a great place to start, with rotating exhibitions featuring both historical and contemporary works. It’s worth check the schedule at The Woodstock Playhouse which features a wide range of productions, festivals and events at a landmark playhouse site in the pages of American theatre history.
The Woodstock Playhouse at the entrance to town in Woodstock , NY
The Mower’s Saturday flea market runs through the end of October and is a quick stop right off the main street in Woodstock. Located directly behind Bread Alone on Saturdays this is great place to get a true feel for Woodstock with local artisans and vendors of all different walks of life.
The Woodstock Byrdcliffe Guild is a historic arts and crafts community located just a few miles from the center of town. The Guild offers a variety of workshops, including pottery, printmaking, and woodworking. During the winter months, they also offer special events like holiday markets and concerts.
Visit a Farm and Go Apple Picking
Fall is harvest season in the Catskills, and the area’s many farms and orchards offer a bounty of fresh produce and seasonal activities. Apple picking is a popular fall pastime, and several local orchards, including Kelder's Farm and Stone Ridge Orchard, offer pick-your-own apples and other fall produce. Many farms also offer hayrides, corn mazes, and pumpkin patches, making them great destinations for families.
Attend a Festival or a Music Show
Woodstock hosts several festivals and events throughout the fall, celebrating everything from music to film to food. The Woodstock Film Festival, held annually in October, showcases independent films from around the world and attracts filmmakers and movie buffs from near and far. The Belleayre Fall Festival has a ton of fun-filled activities for the entire family as you can sample tons of food & beverages, listen to live music, take in the sights with a fall foliage gondola ride, decorate a pumpkin, and much more.
Woodstock’s music scene is active all year round given it’s rich history in all types of music. we suggest checking out the schedules at The Colony (“The Smartest Rendezvous in the Catskills!), Levon Helms Studio (“The Home of the Midnight Ramble” and Bearsville Theater, where Bob Dylan took the safe and cozy world of folk music and married it to rock & roll.
The entrance to Bearsville Theater
Relax and Recharge
Fall in Woodstock is a great time to unwind and recharge. Go on a drive and get lost in the Catskills! As long as you can find your way back to Route 28 and head East you will find your way back to Woodstock. The town's scenic beauty and laid-back vibe make it the perfect destination for a fall getaway. Whether you're sipping hot cider by the fire or soaking in the fall colors on a quiet country drive, Woodstock offers plenty of opportunities to slow down and savor the season.
Fall is an incredible time to visit Woodstock, New York. From the fall foliage to exploring the art scene and local markets, there's no shortage of things to do in and around the town. Fall is still the busy season in Woodstock so it’s suggested to plan your trip and book a few months in advance. We always recommend checking out the Woodstock Chamber of Commerce Calendar of Events.
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