Labor Day weekend is the perfect excuse to hit pause, escape the city, and soak up the last days of summer in the Catskills. Whether you’re craving outdoor adventure, family-friendly activities, or a cozy cabin retreat, Windham, NY has something for everyone.
To help you plan your getaway, we’ve rounded up the best things to do in and around Windham — plus tips on making the most of your long weekend at Unwind Windham, your home base for four-season relaxation and fun.
1. Hit the Trails & Enjoy the Views
The Catskills are famous for their scenic hiking trails, and Labor Day weekend is one of the best times to explore them.
- Windham High Peak Trail — A moderate 6.5-mile hike with stunning panoramic views.
- Kaaterskill Falls — A must-visit! This two-tiered waterfall is one of New York’s tallest and most breathtaking.
- The Windham Path — Perfect for families, this 1.5-mile loop offers mountain views and a peaceful stroll.
Pro Tip: Pack a picnic, stop by a local market for fresh bites, and take in the gorgeous late-summer scenery.
2. Explore Local Events & Live Music
Windham comes alive over Labor Day weekend with food, music, and community celebrations. Some local highlights:
- Windham Mountain’s Labor Day Festivities — Enjoy live bands, food trucks, and craft beers.
- Tannersville Crazy Race & Street Fair — A short drive away, this quirky tradition features live music, street vendors, and a soapbox derby that’s fun for all ages.
- Outdoor Dining & Local Brews — Check out spots like Ze Windham Wine Bar, The Vineyard at Windham, or Hunter Mountain Brewery for good food and relaxed vibes.
3. Cool Off at Local Lakes
If the summer heat lingers, take advantage of the Catskills’ refreshing swimming spots:
- Colgate Lake — Perfect for a family picnic and a quick dip.
- North-South Lake — A short drive from Windham, this scenic lake offers kayaking, fishing, and plenty of space to relax by the water.
4. Family Fun at Windham Mountain Adventure Park
For families or friend groups looking for something exciting, the Windham Mountain Adventure Park is a must:
- Mountain biking trails
- Scenic chairlift rides
- Ziplining and outdoor climbing
- Snow tubing in winter — but late summer offers plenty of warm-weather thrills, too!
5. End Your Days Unwinding in Luxury
After a day of adventure, there’s no better place to relax than Unwind Windham. Our luxury 4-bedroom mountain retreat has everything you need for a perfect long weekend:
- Outdoor hot tub with sweeping mountain views
- 3-person sauna to melt away stress
- Private home gym for fitness enthusiasts
- Ultimate game room with arcade games, foosball, and virtual pinball
- Kids’ playset, family amenities, and plenty of space to sleep up to 12 guests
Whether you’re spending the day exploring Windham or simply want to enjoy a slow, cozy weekend with loved ones, Unwind Windham is your ideal Catskills home base.
Plan Your Labor Day Escape
Labor Day weekend fills up fast in the Catskills, so now’s the time to plan your getaway. Whether you’re hiking, sipping local wine, catching live music, or soaking in the hot tub, Windham has everything you need for an unforgettable weekend.
Book your stay at Unwind Windham and make this Labor Day one to remember!
Unwind Windham Blog 
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