Event Information

WINDHAM’S 32ND ANNUAL AUTUMN AFFAIR

Saturday and Sunday, October 10-11 - 10 AM-5 PM
Main Street and WAJ School Grounds - FREE Admission and Parking

Windham’s 32nd Annual Autumn Affair returns Columbus Day Weekend with two full days of fall fun, live music, great food, shopping and activities throughout the village.

WEEKEND HIGHLIGHTS INCLUDE:

- Live Music and Entertainment: Lexy Grey and the Urban Pioneers take the Main Stage Saturday, with Steel performing Sunday. Enjoy even more live music and entertainment throughout the weekend at Windham Local, Windham Wine and Liquors, Millrock and other Main Street locations.

- Autumn Affair Baking Competition: Calling all bakers! Saturday inside Centre Church, amateur and professional bakers are invited to enter their favorite cookies, pastries and pies. Plus, stop in to sample treats from the Sharing Table while supporting the Windham Community Food Pantry.

- Family Fun: Wes Laraway Wildlife Exhibit, Hudson Valley Reptiles, Vidbel Homestead Petting Zoo, Mike the Juggler, Touch-a-Truck, Spooky Hay Maze, kids arts and crafts, temporary tattoos, K-9 Sheriff demonstrations and axe throwing.

- Main Street Happenings: Stroll Main Street and discover seasonal food and drink specials, sidewalk sales, tastings, live entertainment and plenty of reasons to stop into Windham’s local shops and businesses throughout the weekend.

- Food and Local Flavor: Methodist Church Apple Fest with its famous apple fritters and baked goods, Main Street Market’s sausage and peppers, authentic Greek specialties, wine and spirit tastings, autumn cocktails, Oktoberfest offerings and more.

- Shop and Stroll: More than 50 vendors, artisans and makers join Main Street shops for a weekend filled with local shopping and fall finds.

- More Weekend Favorites: WAJ Ski Swap, Coldwell Banker Village Green Realty’s Doggie Photo Contest and plenty more happening throughout the village.

Come spend the day, meet up with friends, shop local and enjoy one of Windham’s favorite fall traditions.

Presented by the Windham Chamber of Commerce
movingwindhamforward.com


Website: https://go.evvnt.com/3853393-0?pid=5268

Date and Time: On Sat, 10 Oct 2026 10:00 - Sun, 11 Oct 2026 17:00

Category: Festivals