Unwind Windham Blog

Plan your perfect Catskills getaway this fall!

September is one of the best times to visit Windham, NY — the air is crisp, the leaves are starting to change, and the town is buzzing with festivals, markets, and outdoor fun. Whether you’re here for a relaxing mountain retreat or an action-packed weekend, there’s something for everyone.

And the best part? Unwind Windham is the perfect home base — a stunning mountain chalet tucked away in the heart of the Catskills, just minutes from all the local events.

Here’s your guide to exciting things happening this September in Windham:

1. Windham Farmers’ Market

📍 Main Street, Windham
🗓️ Every Saturday in September | 9 AM – 1 PM

Start your weekend like a local at the Windham Farmers’ Market!

Every Saturday, the town comes alive with fresh produce, handmade goods, artisanal cheeses, baked treats, and local crafts.

Grab a coffee, browse the stalls, and stock up on farm-fresh finds for your stay at Unwind Windham — perfect for cooking a cozy dinner back at the chalet.

Pro Tip: Arrive early for the best selection and enjoy live music while you shop!

2. Labor Day Fair

📍 Windham Mountain
🗓️ September 3 – 7, 2025

Kick off September with one of Windham’s most beloved traditions — the Labor Day Fair! Expect a weekend packed with rides, games, local vendors, live entertainment, and family-friendly activities.

From craft booths to food trucks serving Catskills favorites, there’s something for everyone. This is a great chance to soak up the lively small-town vibe before summer officially winds down.

Don’t miss: The fireworks show — the perfect way to end your Labor Day weekend getaway!

3. Catskill Mountain Thunder Motorcycle Festival

📍 Blackthorne Resort, East Durham (15 mins from Windham)
🗓️ September 9 – 14, 2025

Get ready for roaring engines, live music, and non-stop fun at the Catskill Mountain Thunder Motorcycle Festival — one of the largest motorcycle events in the region!

Whether you ride or just love the energy, you’ll find:

• Bike shows & stunts
• Live bands & concerts
• Food vendors & local brews
• Scenic rides through the Catskills

It’s an exciting, high-energy event that draws visitors from all over the Northeast — and staying at Unwind Windham gives you the perfect balance between the festival buzz and a peaceful mountain retreat.

Make Unwind Windham Your September Escape

After a day of exploring Windham’s best events, come back to your private mountain oasis. Unwind Windham offers everything you need for the ultimate Catskills getaway:

✨ Hot tub + sauna for ultimate relaxation
✨ Modern kitchen & outdoor grill for cozy meals
✨ Spacious deck with mountain views
✨ Game room & entertainment spaces
✨ Minutes from Windham Mountain & local events

Whether you’re here for the farmers’ market, the Labor Day Fair, or the motorcycle festival, Unwind Windham puts you right in the heart of it all.

📌 Slots are filling up fast! Book your getaway now and make the most of this incredible season in the Catskills!