A Cozy Weekend in Windham, NY: Your Three-Day Mountain Getaway
Tucked into the Northern Catskills, Windham makes weekend escapes feel easy with great food, small-town charm, year-round mountain fun, and plenty of spots to slow down. Begin your stay with Red Cottage, where thoughtfully designed homes set the tone for a comfortable, unhurried weekend. Whether you’re here for skiing, foliage, hiking, or just fresh air and good meals, Windham and its surrounding towns deliver plenty to explore.
Friday: Settle In + Local Flavor
If you’re coming from the Thruway, make a stop at Red Star Café & Bakery for a fresh pastry and a perfectly brewed coffee to kick off your weekend. With your morning fuel in hand, head to your Red Cottage rental. Take a moment to unpack, kick off your shoes, and breathe in the crisp mountain air.
Once you’re settled, head into town to stock up on local treats and essentials for your stay. Paracasa Gourmet Grocery Store and Haymarket Catskills are perfect for fresh bread, cheeses, and other provisions to enjoy back at your cottage.
When it’s time for dinner, choose between an elegant evening at Restaurant Matilda or casual Italian dishes and a warm, welcoming vibe at Millrock Restaurant & Bar Room. Wrap up the night by the fire, letting the mountain views and crisp air set the tone for the weekend ahead.
Saturday: Mountains, Markets & Art
Start your day with a leisurely breakfast and a cup of coffee at The Windham Local Public House, where friendly chatter and hearty morning fare make ease you into the weekend. Once you’re fueled up, spend the morning exploring the shops and local boutiques! Gem Mercantile is perfect for unique gifts and clothes, while Windham Mountain Outfitters has everything you need if you’re gearing up for an adventure on the trails.
Head up to the mountains depending on the season: Windham Mountain Club and Hunter Mountain offer winter skiing and snowboarding for cold-weather visitors, while summer brings scenic lifts, hiking, mountain biking, and ziplining. Either way, a morning on the mountain is the perfect way to embrace the Catskills.
Stop for lunch at Catskill Mountain Country Store & Restaurant, where classic country-store charm meets hearty, satisfying fare, the perfect stop before an afternoon of exploring.
Spend the afternoon discovering Windham’s creative side. Pop into Windham Fine Arts or Lexington Arts + Science to browse local exhibitions, or explore Elm Ridge Wild Forest for a peaceful walk surrounded by forest trails and mountain views.
After a day of exploring, you have two great options for dinner: Babblers Restaurant & Bar, where comfort food and a relaxed atmosphere make for a satisfying evening, or Cin Cin, serving Italian-inspired dishes in a warm, inviting setting, perfect after a full day of hiking, shopping, and wandering. Wrap up the evening with a nightcap or a quiet moment back at your Red Cottage, letting the mountains settle around you as the weekend unfolds.
Sunday: Slow Morning + Sweet Farewells
Take your time waking up and enjoy a relaxed morning at Babblers Bakery, where fresh pastries and coffee set the tone for a slow, easy start. If time allows, treat yourself to a little pampering at The Windham Spa. A massage, facial, or soak in the sauna is the ideal way to unwind before hitting the road, leaving you refreshed and ready to carry a bit of the Catskills magic back home.
Before you head home, make a stop at Maple Hill Farm. This family-run farm offers fresh local goods and a taste of Catskills country life, making it the perfect final stop to savor the region.
Mountains, Meals & Memories
Whether you’re carving the slopes at Windham Mountain or Hunter Mountain, browsing local shops and art galleries, savoring fresh pastries at Red Star Café & Bakery, or relaxing fireside at your Red Cottage rental, a weekend in Windham is pure Catskills magic. With mountain views, charming small-town streets, and locally made food and drinks at every turn, it’s the perfect mix of adventure, cozy comfort, and a little Northern Catskills charm to recharge your spirit.
