Snow-covered trails at Windham Mountain offer classic Catskills terrain and wide-open winter views. Photo: c/o Windham Mountain Club
EB’s Top 5 in Windham:
• Hiking the Black Dome and Blackhead Mountain Trail: A favorite among seasoned hikers, this six-mile loop delivers some of the most dramatic vistas in the Catskills. Rugged terrain and steep elevation gains make this a more advanced route — sturdy boots and solid footing are strongly recommended.
• Shopping & Coffee at Paracasa: Part provisions shop, part coffee bar, this curated spot is ideal for stocking up on pantry staples, local goods, and housewares. Grab a coffee at the counter, then take your time exploring the shelves
• Skiing at Windham Mountain: The mountain stretches 3,100 feet high and features 285 skiable acres for skiers of all abilities. Windham’s adaptive sports program also expands access to the mountain.
• Dinner & Dessert at Matilda: When at Matilda, be sure to save room for dessert and an after-dinner drink – specifically, the chocolate mousse paired with an espresso martini or flavorful amaro.
• Pitstop in Kingston, NY: Many visitors make a pitstop in Kingston en route to Windham, exiting at Exit 19 off the NYS Thruway. The Stockade District and Rondout area are both worth a visit. Check out our Guide to Kingston for specific recommendations.
Tucked into the northern Catskills, the town of Windham has long drawn visitors with its mountain air and small-town charm. Best known for its ski resort, it wears its winter reputation well — but there’s just as much to explore when the snow melts. Think ridge-top hikes with sweeping views, browsing shops on Main Street, and winding down with cocktails by a fire pit after a spa treatment.
Some come for Windham Mountain’s well-groomed trails and adaptive ski programs; others come for fall hikes along the Blackhead range or summer brunches overlooking the Catskills. Season to season, Windham strikes a balance between outdoor adventure and small-town ease — the kind of place where both a mountain summit and a greenhouse-scented home goods shop can be trip highlights. Read on for our Windham area guide to inspire your itinerary.
What to Do in Windham, NY: Skiing, Shopping, and Scenic Hiking
The shelves at Gardenheir’s Windham location are stocked with gardening attire, gifts, decor, and more. Photo: c/o Gardenheir
In winter, Windham Mountain draws skiers and snowboarders from across the Northeast. The public-private resort is especially notable for its adaptive snow sports program, which includes options like two-track skiing, three-track skiing, bi-skiing, and monoskiing, making the mountain more accessible than most.
Once the snow melts, Windham becomes a hub for hiking and outdoor exploration. The Windham Path offers an easygoing 1.5-mile loop past open meadows, woodlands, and the Batavia Kill stream. It’s ideal for a short stroll with scenic mountain backdrops. For more experienced hikers, the Black Dome and Blackhead Mountain trail climbs over nearly six miles of rugged terrain, delivering panoramic Catskill views that are particularly stunning in the summer.
Those looking to unwind can head to The Windham Spa, a Certified Green Spa offering a full slate of treatments, including cannabis-infused therapies. Afterwards, browse the curated selection of home goods, gardening tools and apparel, skincare, and more at Gardenheir, whose Windham location blends contemporary design with the town’s rural charm.
Where to Eat + Drink: The Best Bars and Restaurants in Windham, NY
After a day skiing, hiking, or shopping in town, settle into a seat at The Henson’s wraparound bar. Photo: c/o The Henson
Windham’s dining scene strikes a balance between casual comfort and refined mountain fare. Start the day with breakfast at Day June Luncheonette in nearby Hensonville, where diner staples like pancakes and omelets are served in a space that blends nostalgic design with modern sensibility. For a brunch with views, Babblers at Wylder Windham offers seasonal menus and a polished yet relaxed atmosphere.
Dinner options range from elevated regional cuisine at Matilda at The Henson, where ingredients are sourced locally and dishes change with the seasons, to fireside cocktails and hearty mains at the Bunkhouse Lounge in Eastwind Windham – a cozy, alpine-inspired hotel with expansive views of the surrounding landscape.
