Woodstock, NY has long been a haven for artists, musicians, and dreamers—but come autumn, it transforms into a leaf-peeping paradise.
Recently named one of the best small towns in the U.S. to see fall foliage by Travel + Leisure, this charming Catskills town mixes vibrant fall colors with galleries, live music, and hidden natural gems, all within an easy two-hour drive from NYC.
Known as “The Arts Colony of the Catskills,” Woodstock earned its nickname thanks to a long tradition of artists, musicians, and creatives flocking to the area for inspiration.
From its gallery-lined main street to its historic studios and theaters, the town exudes a vibrant, bohemian energy that feels especially magical during the fall!
Quaint cafés, independent bookstores, and live music venues make wandering around downtown a treat, while the surrounding Catskill forests and mountains provide a perfect natural backdrop for leaf-peeping adventures.
Here’s your guide to the best spots to see the fall foliage—and the hidden gems that make Woodstock uniquely special.
Top fall foliage viewing spots in Woodstock, NY
Fall in Woodstock isn’t just about the charming main streets—you’ll find some of the region’s most spectacular colors by venturing a little further into the surrounding hills, trails, and secret spots.
Here’s where to go for the ultimate autumn experience:
Overlook Mountain Fire Tower Hike
This 4.6-mile round-trip trek is the must-do foliage adventure.
Climb past the spooky ruins of the Overlook Mountain Hotel to the fire tower for 360° panoramic views of the Catskills and Hudson Valley ablaze in autumn color.
Insider tip: mornings or late afternoons provide the best light—and fewer crowds.
Ashokan Rail Trail & Onteora Lake Trail
For a bit of an easier stroll, these trails offer radiant fall scenery without the sweat!
Rolling woods and reflections over the Ashokan Reservoir make for peaceful, postcard-perfect moments.
Kaaterskill Falls Excursion
A short drive from Woodstock, this iconic two-tiered waterfall is framed by vivid foliage!
Kaaterskill Falls is one of New York’s tallest waterfalls at 260 feet, and makes for one of the most stunning views you’ll ever see. Go early for quieter, more intimate views of one of New York’s best cascades.
Woodstock Waterfall Park
This park is one of our favorite hidden gems, and most people miss it completely when visiting Woodstock!
Tucked off Tinker Street at Tannery Brook Road, this tiny waterfall known as “Woodstock Falls” is a local favorite—perfect for a serene break amid your downtown explorations.
Tinker Street & Drum Circles
Of course the parks and woods are always best to see the foliage, but you can’t forget about the heart of the charming downtown Woodstock too!
Stroll the heart of the village, specifically Tinker Street, to soak in gallery shows, pop-up markets, live music, and spontaneous drum circles. There’s plenty of changing colors lining the main streets.
Art galleries & museums
Art AND a view?!
Why yes, Woodstock’s beloved art galleries and museums are always loaded with fall programming, and are just a quick eyeshot from loads of fiery foliage.
Some to check out include the Woodstock Artists Association & Museum, the Byrdcliffe Guild, and ever-changing local galleries.
Plus, the annual Woodstock Film Festival (Oct. 15–19, 2025) is also a huge autumn draw and it’s happening this week!
Fall events & seasonal activities near Woodstock
Ready to plan your fall foliage to excursion to Woodstock?! Consider planning it around some of these awesome seasonal activities for the ultimate autumn adventure.
- Apple picking & farm visits – Nearby Kelder’s Farm or Stone Ridge Orchard for pumpkin patches, hayrides, and pick-your-own apples are always a fun time!
- Peace, Love & Pumpkins (Bethel Woods) – This walk-through Halloween experience in nearby Bethel features magical light displays, and festive activities from Oct. 10–Nov. 2. More info