10 Best Things to Do in Windham, NY on a Regular Summer Weekend

Windham rocks, but don't take my word for it! Experience it yourself.

There was a lot of controversy surrounding Windham Mountain turning into a private club in the last few years. Longtime skiers grumbled, Ikon Pass holders felt shut out, and locals worried the change would drain the town of its energy. But from the hustle and bustle on Main Street, it seems the change did the town and the surrounding areas a lot of good. The place is happening! Restaurants have reservation lines, boutiques are humming, and the whole village has a polish that feels earned rather than manufactured. Here are the coolest and most fun things to do in Windham this summer, from the perspective of a sophisticated traveler.

1. A Country Brunch with the Animals. Before you head out for the day, swing by the Catskill Mountain General Store for a relaxed brunch. This General Store is the kind of spot where you can linger over coffee while the kids wander over to the on-site petting zoo. It's a genuine crowd-pleaser, and the store's resident cat, Mexican Hat, has no problem mingling with the barnyard crowd or soaking up attention from visitors. A perfectly local, unhurried way to start a Windham morning.

2. Stroll the Town Windham's walkable strip is the heart of the weekend. Pop into Windham Mountain Outfitters for gear, Briars and Brambles Books for a Hudson Valley read, and Gardenheir for the chicest garden tools you never knew you needed. Grab a pastry from Babblers Bakery along the way.

3. Hike the Windham Path. This dog-friendly, 1.5-mile nature walk is easy enough for a lazy morning but scenic enough to feel like an accomplishment. It's the perfect low-commitment intro to the Catskills before you tackle anything steeper. Please remember to pick up after your dogs!

4. Summit Windham High Peak. For travelers who want their views earned, this roughly 6.8-mile trail delivers sweeping ridge lines and solid birdwatching. Start early, pack water, and save the afternoon for recovery mode.

5. Chase Kaaterskill Falls. A short drive away, this out-and-back trail leads to a dramatic 260-foot cascade — one of the most photographed spots in the Catskills, and worth the moderate climb.

6. Cool off at a lake beach. CD Lane Park and Colgate Lake both offer sandy stretches for swimming and lounging, a refreshing counterpoint to a morning of climbing.

7. Tee off with Mountain Views. Windham Country Club's 18-hole championship course rewards good players with elevation changes and postcard scenery, while Christman's Windham House offers a mellow 9-hole round for anyone who'd rather not keep score too closely.

8. Taste something local. The Vineyard at Windham runs a reservation-only tasting room pouring rosé, sparkling, and estate reds — a genuinely upscale addition to a town once known mainly for lift tickets.

9. Eat like you mean it. Reserve a table at Matilda inside The Henson, order the veal at Millrock, or settle into the lively bar scene at Prominence for Italian-American classics. For something more casual, The Windham Local blends American comfort food with Thai flavors — try the pork soup dumplings.

10. End the day with a cocktail and a view. Head to Eastwind's Bunkhouse Lounge or Babblers at Wylder for craft cocktails, live music, and that unmistakable resort-town glow as the sun drops behind the ridgeline.

The irony isn't lost on longtime visitors: a controversial members-only shift at the mountain seems to have pushed the town itself upmarket in the best possible way. Restaurants have gotten better, shops feel curated rather than touristy, and streets have the kind of buzz that used to be reserved for peak ski weekends. Whether you're hiking to a waterfall at sunrise or sipping rosé at sunset, Windham in summer proves that a mountain town's appeal was never just about the mountain.

Planning your trip? Check StayCatskills.com for the best places to stay in and around Windham this season.

Whether you're visiting for the first time or a Catskills regular, there is always something new to discover. We hope to see you at the Barnhouse soon.