This Weekend Autumn Magic Meets Main Street
Every autumn, as the leaves begin to drop and the air turns crisp, excitement swells in our little mountain town. It’s the sure sign that the Autumn Affair is just around the corner.
For two days, Windham’s Main Street transforms into a celebration of community, creativity, and color. Local artisans, food trucks, and musicians fill the streets, framed by the golden backdrop of the season.
Now in its 31st year, this beloved festival promises to be one of the biggest yet. The kind of fall weekend that reminds you why life in the mountains feels so special.
Windham Autumn Affair returns this weekend.
Food & Artisan Market
Stroll through the festival and discover handmade goods, cozy knits, seasonal produce, and plenty of hot cider and bites from local food trucks. It’s the perfect mix of small-town flavor and mountain charm.
Live Music All Weekend Long
Catch music all weekend long, with Ryan Clark taking the stage at the Center Church from 12–4 PM on Saturday. Enjoy live performances throughout Main Street from local and regional musicians, bringing the perfect fall soundtrack to town all weekend long.
The Great Windham Bake-Off
A hometown favorite returns as bakers from across the Catskills compete for the title of Best Autumn Dessert. Sample pies, pastries, and more. A delicious celebration of community and creativity.
Book The Outpost
Stay just minutes from Main Street and the festival action at Windham Mountain Club, where your autumn escape includes mountain-view lodging, elevated dining, access to The Spa, The Gym, and Member Dining. There’s no better way to celebrate the season than with a weekend in the mountains.
Windham Mountain Club