Windham Chamber of Commerce Announces 31st Annual Autumn Affair

WINDHAM — The Windham Chamber of Commerce will host the 31st Annual Autumn Affair on Columbus Day weekend, October 11–12, 2025, from 10:00 a.m. to 5:00 p.m. along Main Street in Windham. Admission and parking are free.

Now in its 31st year, the Autumn Affair has grown into one of the Catskills’ most anticipated seasonal festivals, attracting thousands of visitors to enjoy the sights, sounds, and flavors of fall.

Entertainment & Music: On Saturday, country-pop recording artist Ryan Clark will perform live, while Sunday will feature the return of Soulsense, bringing R&B favorites from the summer concert series.

Family Attractions: The festival offers something for all ages, including Wes Laraway’s Wildlife Exhibits, Hudson Valley Reptiles, the Vidbel Homestead Petting Zoo, and the Windham Fire Department’s Touch-a-Truck. Children can enjoy crafts, games, axe throwing, and the Catskill Mountain Country Store’s Spooky Hay Maze, while adults can test their swing at the new golf simulator.

Community Traditions: Local favorites return, including the Methodist Church Apple Fest on Saturday with its famous apple fritters, enter the Baking Competition inside the Centre Church, and the Coldwell Banker Village Green Doggie Beauty Photo Contest.   Food & Vendors: With more than 60 vendors, visitors can browse handmade crafts, sample seasonal treats, and enjoy local favorites like Main Street Market’s sausage and peppers, along with wine and spirit tastings at Windham Wine & Liquors.

The Autumn Affair is a celebration of Windham’s community spirit, Main Street charm, and the beauty of fall in the Catskills.

For more information, visit www.movingwindhamforward.com.