Windham’s 32nd Annual Autumn Affair

Name: Windham’s 32nd Annual Autumn Affair
Start: 2026-10-10
End: 2026-10-11
Location: Main Street in Windham

Oct 10–11, 2026
Main Street in Windham

Arts & Culture
beverage
Food & Drink
Events
Family Fun
festivals
Music

Celebrate the vibrant colors of fall in the Gem of the Catskills at the 32nd Annual Autumn Affair.

Happening Columbus Day weekend in Windham, October 10 & 11, 2026, from 10 AM to 5 PM daily. This beloved Catskills tradition brings friends, neighbors, and visitors together for two days of live music, delicious food, unique shopping, and family fun.

Main Street will come alive with more than 50 vendors offering local crafts, seasonal treats, and specialty foods, plus sidewalk sales from Windham’s Main Street businesses. Festival highlights include hay wagon rides, axe throwing, chainsaw carving demonstrations, and kid-friendly entertainment.

Free parking is available at Windham Mountain Club and throughout town, and admission is free so bring the family, explore the festivities, and enjoy the beauty of autumn in the Great Northern Catskills.

Windham’s 32nd Annual Autumn Affair — image 1

Windham’s 32nd Annual Autumn Affair — image 2

1 / 6

Event Details

Start: October 10, 2026
End: October 11, 2026

Location
Main Street in Windham
Address
Main Street
Windham, NY, 12496
Visit Website
Phone
518-755-2573
Email
windhamchamberofcommerce@gmail.com

Loading map...

View on Google Maps

Find this event at

Windham, NY

Wylder Windham

There’s something different about Windham. Located in the Great Northern Catskills, it’s a place that families and friends have quietly escaped to for generations in pursuit of natural beauty and outdoor adventures. That’s exact what you will find at Wylder Windham! With 20 acres of land and the Batavia Kill running through it, our family-friendly all-season resort is filled with endless opportunities for relaxation and fun. Whether tubing on the creek, having a delicious meal at the on-site Babblers Restaurant and Bakery, gathering with friends around the firepit or going skiing at nearby Windham Mountain, this is a place that captures the nostalgic spirit of the Catskills and celebrates the timeless pleasures that this land has to offer. Elevate your Wylder Windham getaway with our Couples Retreat Add-On, designed for romance and relaxation. For just $65, enjoy: In-room bottle of Prosecco to toast to your special moments Decadent chocolate-covered strawberries for a sweet indulgence Private sauna reservation for ultimate relaxation Whether you’re celebrating an anniversary, a special occasion, or simply escaping for a cozy weekend, this add-on sets the perfect mood. How to Book: Select Couples Retreat Add-On when booking online or call 518.734.4510 to reserve your romantic escape today! Host your wedding, corporate event, meeting or retreat at Wylder Windham. Follow us on Facebook and Instagram

See Details →

Windham, NY

Union + Post

Union + Post is a boutique hotel with 12 thoughtfully designed rooms and an on-site restaurant in New York’s Northern Catskills. Located in the charming village of Windham—150 miles north of NYC and an hour south of Albany—Union + Post is surrounded by scenic beauty, hiking trails, and ski slopes, offering the perfect four-season getaway. The on-site restaurant highlights New American fare with seasonal ingredients inspired by local farms. Guests can unwind at the original hickory-wrapped bar, relax by cozy fireplaces, or enjoy stunning views from the wrap-around windows. For a more intimate setting, visit the second-floor Library or step onto the outdoor deck for panoramic views of Windham. Union + Post is dog friendly. Book your wedding, private event, leadership retreat or group getaway at Union + Post. NEW HILLTOP HOME RENTAL: Discover serenity in Union + Post’s brand-new 5-bedroom hilltop home. This elegant retreat blends privacy, tranquility, and modern sophistication, offering guests spacious interiors paired with all the comforts of contemporary amenities. Wake up to panoramic mountain views and stunning sunrises, relax in expansive outdoor spaces perfect for entertaining, and enjoy the ultimate in Windham living. Find us on Facebook and Instagram

See Details →

Windham, NY

Hotel Vienna

Our multiple mountain decks and social fire pits provide the perfect backdrop for your morning coffee or a relaxing sunset. Whether you are coming for the mountains, hiking, or just relaxing on our land, Hotel Vienna is the perfect escape for couples and meaningful gatherings among Windham, New York hotels. Hotel Vienna offers an ideal setting for Retreats, Group Gatherings and Mountain Escapes. WE ARE PET FRIENDLY! Like us on Facebook Follow us on Instagram

See Details →

Windham, NY

Eastwind

Eastwind Hotel is a scenic, welcoming boutique hotel in Windham, blending its roots as a 1920s bunkhouse for hunters and outdoor enthusiasts with Scandinavian-inspired design for an upscale mountain retreat. Set on 17 acres, the property offers 32 accommodations, including seven Lushna Cabins and three Lushna Suites with private decks and panoramic views for a refined glamping experience. Pet-friendly rooms are available for an additional fee, with thoughtful welcome amenities for furry guests. Guests can also enjoy Dandies the onsite restaurant inviting guests to savor connection, flavor, and après moments in a modern mountain setting. Our property is ideas for corporate and wellness retreats, and creative group gatherings. We also offer specially curated events designed to inspire, restore, and reconnect. Also offering EV charging stations.

See Details →

Windham, NY

Christman’s Windham House Country Inn and Golf Resort

A family- run country inn and golf resort in Windham, NY, gem of the great Northern Catskills. 27 holes of golf, hotel, bar, casual dining, pool, stay & play packages, events, corporate and golf retreats. Families and groups welcome. Other amenities include: 300 acres of grounds 18 hole mountain golf course 9 hole valley golf course Restaurant Lounge/bar Game room Tennis EV charging stations Find us on Facebook Follow us on Instagram

See Details →

Windham, NY

Cave Mountain Motel

Children 12 and under stay free. Nestled just 1.5 miles from Windham and a short drive from Hunter Mountain, Cave Mountain Motel offers relaxed, friendly hospitality in the heart of the Great Northern Catskills. Guests enjoy clean and comfortable rooms, mountain views, and easy access to year-round outdoor adventures. From trout fishing, hiking, and biking to summer concerts, fall festivals, and winter sports there is so much to explore locally all year around. With amenities including free WiFi, cable TV, individual A/C and heat, and a complimentary continental breakfast, Cave Mountain Motel provides a cozy, convenient base for exploring Windham, Hunter, and the scenic Catskill Park.

See Details →

Windham, NY

Antique Rose Inn Windham

Enjoy daily housekeeping, with refrigerators and irons available upon request. Relax on the outdoor terrace or wander through the peaceful garden, and take advantage of tour and ticket assistance, a picnic area, and access to a nearby fitness facility at a discounted rate. A ski shuttle is available for easy mountain access. ATTENTION WINDHAM MOUNTAIN SKIERS: Guests with confirmed reservations at the Antique Rose Inn Windham or Beds on Clouds receive guaranteed access to lift tickets, even on sold-out days. Simply call us for your code to purchase your lift tickets. Wake up each morning to a complimentary full breakfast served from 7:30 to 9:00 AM.

See Details →

Windham, NY

Windham Fine Arts Gallery

Windham Fine Arts is a contemporary gallery located in the heart of historic downtown Windham, New York. After a three-year restoration of its original 1855 structure, the gallery opened in 2001 and now offers over 3,000 square feet of curated space. Showcasing both local and internationally acclaimed artists, the gallery hosts solo and group exhibitions, as well as cultural and art events year-round.

See Details →

Similar Events

Windham, NY

Next: Sep 5, 2026 (+1 more)

10th Annual Pottery Festival

Catskill Mountain Foundation invites you to the 10th Annual Pottery Festival at Thyme Field at Sugar Maples Center for Creative Arts during Labor Day weekend 2026. The festival celebrates pottery and sculptural clay, featuring 10 talented local potters, including four weekly faculty members, alongside six visiting professional ceramic artists from across the region. More than a showcase of exceptional craftsmanship, the festival celebrates the important role of art in creating vibrant, healthy communities while offering visitors a chance to enjoy the beauty of the Catskills and support local artists. Sat, September 5th, 11am – 5pm Sun, September 6th, 11am – 4pm

See Details →

Windham, NY

Sep 19, 2026

Oktoberfest at Mountain King Brewing

Get into the Oktoberfest spirit at Mountain King Brewing in Windham on Saturday, September 19th, for an afternoon of festive fun, live music, craft beer and more as the Great Northern Catskills welcomes the fall season. Celebrate with limited-edition Oktoberfest glassware, and fresh food from Chef Luke’s Fresh Start Food Truck. Come dressed for the occasion and show off your best Oktoberfest-inspired look for the Best Dressed Contest. Whether you’re planning a fall getaway to the Great Northern Catskills or looking for things to do in Windham, this Oktoberfest celebration is a fun way to enjoy local craft beer and the lively atmosphere of the season.

See Details →

Windham, NY

Next: Sep 11, 2026 (+2 more)

September Women’s Reading Retreat

Each book retreat centers on a new, trending novel or memoir, author talks, and wellness activities. Our Sept. 11–13 retreat selection, “Extra Sauce” by Zahra Tangorra, was recently named one of Amazon’s Best Books of 2026 so far! A raw and spirited memoir from chef and writer Zahra Tangorra, exploring the meals, relationships, and experiences that shaped her life, along with themes of family, friendship, grief, and the comfort found through food. The retreat begins with welcome drinks, a catered dinner, and a relaxing meditation before a day of mushroom foraging, a private chef dinner, and lively book discussions. Enjoy plenty of time to read, rest, explore, and unwind in between shared meals and activities. The weekend concludes with a final breakfast and checkout on Sunday morning.

See Details →

Get directions Visit website

Windham’s 32nd Annual Autumn Affair

Celebrate the vibrant colors of fall in the Gem of the Catskills at the 32nd Annual Autumn Affair.

Event Details