Plan a Winter Escape to the Catskills

The Catskills have long been a lure for New Yorkers looking to escape the urban chaos, and enjoy fresh air and an outdoor lifestyle. The area’s golden age was in the 1940s and 1950s, when families would decamp here and stay in a resort for the entire summer. This era was perfectly depicted in episodes of The Marvelous Mrs. Maisel, when the aspiring stand-up comic swapped steamy New York for the Catskills.

While those huge resorts are mostly gone, the Catskills are still enticing New Yorkers (and those from further afield) craving fresh air and outdoor pursuits, even for just a weekend. Large hotels have been replaced by smaller boutique properties and the area has become a design driven destination. Here’s how to spend the perfect winter weekend in the Catskills that combines winter sports with stylish stops.

The new Eastwind hotel in Windham is a hipster take on a mountain lodge-- think battered leather armchairs and faded rugs alongside mid-century modern pieces. The vibe is casual and family friendly, and everyone shows up at breakfast in their ski gear.

The 16 guest rooms are spread out among the main lodge, or in a separate building that looks like a retro motor lodge. The most stylish accommodation here is a row of A-frame glamping cabins but guests will hardly be roughing it. The cabins have Frette linens and the separate bathrooms are just as beautiful. None of the rooms have televisions which encourages guests to warm up by the fire in the main lodge with a drink or make a dash for the outdoor sauna. On weekend mornings there’s a continental breakfast buffet which doubles as a bar area when the sun goes down.

Eastwind makes a perfect base if you’re looking to ski at Windham Mountain Resort which is just minutes away. Windham Mountain has 1600 vertical feet to enjoy, and plenty of new upgrades for the season. There’s new RIFD lift passes and a high speed six passenger chairlift. It can be a challenge to eat healthy on a ski day but not at Windham—lunch options include steaming bowls of ramen as well as sushi. If your muscles are sore after a day on the slopes, Windham Mountain has an onsite spa for massages and yoga classes.

If cross-country skiing is more your speed, head to the track on North-South Lake – or just hike around the lake and breathe in the crisp air. If you’re tempted to try fat biking, which is essentially mountain biking in the snow on large tires, Bearpen Mountain rents everything you need. They also rent out snowshoes and ice skates. If you prefer to keep it simple, just go for a bracing walk along the Windham Path, an easy loop that starts just outside of downtown Windham. You’ll be rewarded with views of the Catskills Mountains and the path meanders past streams and a covered bridge.

When it’s time to thaw out, Windham and the surrounding area offer plenty to do. Shop for one of a kind pieces at the Tannersville Antique & Artisan Center, which is home to 80 vendors or make a pilgrimage to nearby Woodstock, which will soon celebrate the 50th anniversary of the iconic music festival. Some of the best shops are clustered on Tinker Street and Mill Hill Road, such as small batch chocolatiers Fruition Chocolate and the independent bookstore The Golden Notebook. Another indoor option is to make a small detour to explore Olana, the 250-acre estate of the Hudson River School painter Frederic Church. Reservations are essential to tour the Persian-style mansion as well as the landscaped grounds which Church designed himself.

To fuel up for a day on the slopes or exploring the Catskills, try the charmingly ramshackle Maggie’s Crooked Café for oatmeal pancakes, egg white omelets and a green juice, or dig into shakshuka at the Phoenicia Diner, which serves local, seasonal food in a classic diner setting.

One of the best parts of any ski getaway is enjoying après ski so after a day on the slopes pull on your best furry boots and head to Ze Windham Wine Bar. It’s housed in a Victorian home in an unlikely location just behind the Windham post office. But step inside and Ze Windham Wine Bar is the feminine après ski bar of your dreams, complete with marble topped café tables, twinkling lights and plates of charcuterie and a superb wine list. Children are welcomed and can enjoy hot chocolates while adults sip their wine.

For dinner make a reservation at Chicken Run (you’ll have zero chance of getting in without one). It’s an unassuming spot on the outskirts of town but the main reason to come here is for the outstanding aged beef. This is a place that takes it meat seriously. There’s a butcher counter onsite, and you’ll hear the butcher using his band saw to cut thick slabs of rib eye and porterhouse while you’re enjoying drinks. There’s also live music and s’mores pits outside.