Craving a peaceful mountain escape that works in every season? Let me introduce you to Windham. Tucked into the Catskills, Windham has that just-right blend of cozy village vibes and outdoor adventure. I’ve come here to ski in the winter, hike through blooming trails in spring, admire fiery foliage in the fall, and unwind at a spa any time of year. Whether you're after adrenaline or total relaxation, this spot never disappoints. It’s the kind of place I return to again and again.
Best Time to Visit
Windham is honestly a year-round gem—it just depends on what you’re in the mood for. Winter (December through March) is perfect if you're into skiing and snowboarding. I’ve spent entire days on the slopes and evenings by the fire. Fall (September through October) is absolutely stunning, with leaf-peeping drives that’ll blow you away. And in spring and summer, I’ve hiked wildflower-covered trails, biked scenic routes, and enjoyed local festivals that give the whole town a lively, welcoming buzz.
How to Get There
- By Car: I usually make the drive up NY-23—Windham is about 2.5 hours north of NYC and just an hour from Albany. It’s a beautiful drive, especially as you start climbing into the mountains.
- By Air: If you’re flying, the closest airport is Albany International (ALB). From there, it’s an easy 1-hour drive, and you’ll be breathing that crisp mountain air before you know it.
- By Bus: Trailways has routes from NYC to nearby towns like Hunter and Cairo. I’ve used that route before, and from there, you can grab a local taxi or rideshare to get the rest of the way to Windham.
Where to Stay
- Albergo Allegria Hotel & Breakfast Restaurant – I stayed here for a weekend and still dream about the gourmet breakfast. The rooms are cozy and full of country charm—it feels like a home-away-from-home with a touch of luxury.
- Windham Mountain Club Lodging – If you’re skiing, this is the way to go. You can roll out of bed and hit the slopes. It’s upscale, super convenient, and perfect if you want to stay close to the action.
- Hotel Vienna – I’ve recommended this place to friends for years. It’s got chalet vibes, beautiful mountain views, and it’s just minutes from the heart of Windham. Great for couples, families, or a relaxing solo trip.
Top Attractions in Windham, NY
Windham Path
I began with a walk on the Windham Path, a gentle 1.5-mile loop that cuts through meadows and over wooden bridges, with rolling mountains never too far in the background. The trail was well-kept and stroller-friendly, but still quiet enough to hear the crunch of gravel and the rustle of tall grass. Birds called from somewhere off-trail, and the smell of pine mixed with something sweet—clover maybe, or late-season wildflowers. I walked slowly, unhurried, watching sunlight catch on dragonfly wings. The kind of path that doesn’t demand anything from you, but gives plenty.
Windham Fine Arts
Back in town, I stepped into Windham Fine Arts, expecting a brief browse and ending up in something closer to a meditation. The gallery was light-filled and surprisingly expansive, with pieces ranging from abstract oil paintings to stonework that looked like it belonged outside, in the woods. One room had landscapes so vivid they felt like memories you hadn’t made yet. “There’s more quiet in here than outside,” I thought, and let myself linger a while longer.
Five State Lookout
Next came a short drive to the Five State Lookout, perched high enough to see—on a clear day—New York, Massachusetts, Vermont, Connecticut, and New Hampshire. The view lived up to its name. Hills rolled into ridges rolled into distance, with nothing but layers of blue and green all the way to the horizon. A gust of wind pushed at my jacket. I stood at the railing for a long time, just watching, saying nothing, letting the scale of it all do the talking.
Elm Ridge Wild Forest
I took the slower road back into town via Elm Ridge Wild Forest, where trailheads dart off into deeper Catskill territory. I didn’t hike far—just enough to feel surrounded by trees and step onto a soft dirt path that smelled like moss and damp bark. The woods here are old, tall, and quiet. Every branch creaked like a sentence waiting to finish. Even a short loop felt like a reset, like the kind of quiet that stays with you longer than you expect.
Ski, Snowboard, or Hike Year-Round at Windham Mountain
I swung past Windham Mountain after, off-season but still impressive, its trails bare and grass-covered, lifts hanging silent in the wind. I could imagine the winter buzz, the early lift lines and clatter of skis, but today it was still—a mountain catching its breath. A few bikers rode down one of the single-track trails, and someone was raking leaves by a rental lodge. Even without snow, the place carried purpose. Just different layers of the same heartbeat.
Shop and Dine with Charm at The Catskill Mountain Country Store & Restaurant
Lunch was at The Catskill Mountain Country Store, where the menu is part comfort, part local legend. I ordered the grilled cheese with tomato and basil on thick-cut sourdough, plus a side of their butternut squash soup. The sandwich was buttery and crisp, the cheese just sharp enough, and the soup tasted like it had been simmering since sunrise. I sat on the porch, sipping hot cider, listening to wind chimes tap out something tuneless but soothing. Nearby, someone bought a mason jar of jam and a tiny wooden bear. I could’ve done the same, but I had food to finish and no reason to rush.
Windham House
After lunch, I stopped by Windham House, one of those timeless inns that seem built more for front-porch sitting than overnight stays. The lawn stretched wide and green, dotted with Adirondack chairs and one very determined chipmunk. I didn’t go inside—I just walked the grounds, peeking into garden beds and watching a hammock sway slightly in the breeze. It felt like a place that collects stories slowly, in soft voices, over long stays.
Unwind with a Glass at the Cozy Ze Windham Wine Bar
I ended the day with a stop at Cozy Ze, a small wine bar on Main Street. I didn’t drink—I just wanted the view, the vibe, the end-of-day hush. I sat at a table outside with a cup of hot mint tea and a slice of lemon tart. The tart was bright, creamy, edged in a shortbread crust that flaked just enough. Couples chatted softly nearby. Lights glowed under the awning, and the mountain air cooled as the sun dipped. “There’s nothing I need to change about this moment,” I thought. And I didn’t.
Windham At a Glance
- Drive Time from NYC: ~2.5 hours north
- Vibe: Artistic calm wrapped in Catskill air
- Highlights: Gentle trails, sweeping overlooks, small galleries, farm-to-fork comfort
- Best Time to Visit: Fall for foliage and hiking; winter for skiing and fireside views
- Cost: Moderate; most outdoor activities free, dining and lodging range by season
- Hours: Trail access year-round; galleries, shops, and eateries often closed midweek
- Address Base: Start along Main Street and branch out from there
Final Thoughts
Windham isn’t dramatic—it’s composed. It offers still trails, handmade art, porch meals, and the kind of views that don’t shout—they echo. I came looking for a short mountain escape. I left with longer strides, a deeper breath, and a lemon tart I’ll be trying to recreate for weeks.