Windham NY Chamber of Commerce

Welcome to Windham, New York
est. 1798
Gem of the Catskills

Save the Date October 10 & 11th 2026

Windham's Annual Autumn Affair Celebrating 32 years of Fall Fun

Presented by the Windham Chamber of Commerce, this two-day celebration brings Main Street and the Windham-Ashland-Jewett School grounds to life with arts and crafts, local makers and vendors, delicious food, live music, demonstrations, children’s activities, and plenty of fall fun for all ages

Enjoy live music at the Centre Church stage from 12–4 PM both days, featuring Lexy Gray and the Urbaniers on Saturday with classic rock and R&B, and Steele on Sunday bringing an energetic mix of rock and funk.
Throughout the weekend, visitors can explore 60+ vendors, shop local businesses, enjoy food and drink specials, and take part in activities throughout town. Look for spooky hay maze, wildlife exhibits, lawn games, demonstrations, face painting, temporary tattoos, wine and spirit tastings, and more. On Sunday, don’t miss our Autumn Affair Baking Competition and the chance to earn some serious Windham bragging rights!
Surrounded by spectacular Catskill Mountain foliage, Autumn Affair is the perfect excuse to spend a fall weekend in Windham—shop, eat, explore, listen to some great music and celebrate the businesses, organizations and people who make our community special.
Admission is FREE. Rain or shine.
Saturday & Sunday, October 10 & 11, 2026
10 AM–5 PM
Main Street & WAJ School Grounds | Windham, NY
Mark your calendar and come celebrate 32 years of Autumn Affair in Windham!

Vendor applications are still open, but space is limited. Apply online below link:

Windham Chamber of Commerce Autumn Affair Vendor Application Oct 10 & 11, 2026 10 am-5 pm Daily

Check out What's Happening at Windham's Community Center

The Main Street Community Center is a 501c(3) nonprofit organization dedicated to to building a healthy, caring, welcoming, and inclusive environment for all residents and visitors alike.

Main Street Community Center offers a wide range of classes and events for people of all ages.

In addition to our physical location, the Center offers virtual classes, partners with other local organizations and provides off-site opportunities.

The Center's warm and welcoming atmosphere celebrates the idea that unity is at the heart of every community.

See the Programs page to learn what classes and events are upcoming.

5494 Main Street Rt. 23
Windham NY 12496
518-734-4168
Click below for calendar of events

http://www.mainstreetcenter.org/

Photo: Francis X. Driscoll

Native Americans called Windham "The Land in the Sky"

Nestled in the heart of the Northern Catskill Mountains, our beautiful town will enchant you with its gracious way of living. From our beautiful Main Street dotted with outstanding restaurants, breweries, wine bar, award winning accommodations, unique shops and services to an array of outdoor sporting activities nearby.

Windham provides a wealth of year round activities for residents and tourists alike. The surrounding mountains are perfect for hiking, skiing, golfing, biking, fishing, snowmobiling and horseback riding.

Scenic views abound and nature lovers will find much to see. Our streams and rivers provide the angler with a variety of fish, and hunters will find deer, wild turkeys and other game abound.

Fine dining establishments, community festivals, church socials, youth programs, movie theaters, fine art galleries, full service spa, music concerts at the Windham Civic center, cultural events, two golf courses and world class ski resort, Windham Mountain, make Windham a destination to remember and fabulous place to call home