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A Winter Wonderland Weekend in the Catskills

Winters can be brutal in New York City. Following the recent nor’easters, that’s more apparent than ever. All you can do is hit up your neighborhood bodega, fire up the Netflix queue, and bundle under your favorite blanket.

Or you can plan your escape. Instead of spending what’s left of winter avoiding the icy sidewalks and chilly bars, find your winter wonderland. Just a short drive north of the city is the snowy charm of the Catskills. It’s the perfect getaway for a long weekend.

Day 1:

Whether you’re ducking out of work early or playing hooky, hop on a train or jump into a rental and head north. Once you’re out of Manhattan, it’s a quick cruise up to Catskill.

Stop for lunch at Rip Van Winkle Brewing Company. Named after the local folklore, it serves as a charming mascot for the region. With seven in-house microbrews and a menu of delicious bar food, it’s the perfect preface to the weekend.

Walk it off down Main Street in Catskill. A slice of classic Americana, the wooden storefronts invoke an aesthetic of simpler times. Stop at Catskill Country Store for unique souvenirs, artisan soaps, and fresh-baked goods. Hit the stacks at Magpie Bookshop for a good second-hand read. Follow it up with a vintage treasure hunt at House of Tuki.

Head over to Scribner’s Catskill Lodge, and check into your room with a sweeping view of snow-covered mountain-scapes. After an extensive renovation in 2016, the lodge retains its vintage charm infused with a modern motif. It’s a warm mountain oasis for a weekend of snow sports.

Upstate chillin’ ❄️

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Meet up with friends in the Whiskey Lounge for a pre-dinner cocktail until your table is ready. Prospect Restaurant and Bar serves a fun twist on local cuisine, inspired by the Hudson Valley. Chef Joseph Buenconsejo utilizes fresh local ingredients, drawing from the region’s rich agriculture.

Start off with a butternut squash soup, made with pumpkin seed granola, vadouvan crème fraiche, and cashew. The roasted chicken is a perfectly savory main course, served with cauliflower, pine nut milk, and chicken jus. For dessert, enjoy the warm bread pudding, with burnt marshmallow ice cream and cookie crumble.

After dinner, move things to the library. Open up a bottle of local cider over a board game or a round of eight ball. Or just get cozy around the fire until you’re ready for bed. You have a big day tomorrow.

Day 2:

Start your day with brunch at Prospect. You’ll need a healthy and hearty meal for a day at the slopes. Grilled avocado is a perfect choice, served with sprouts, seeds, red onion, seaweed, and fried egg.

Head over to Windham Mountain Resort for some skiing or snowboarding. Lessons are available, for whatever your skill level may be. A full-service spa is also available for your post-ski massage or some high elevation yoga.

Head over to Tannersville for an unbeatable lunch at Mama’s Boy Burgers. A classic diner experience with a colorful Instagram-worthy touch, the menu comes with all our nostalgia-driven favorites. Burgers are made from locally-grown, grass-fed beef with healthy vegetarian options available. They also offer 26 flavors of frozen custard and frozen yogurt.

After lunch, take a stroll down Main Street. Enjoy a coffee and some antique shopping at Twin Peaks Coffee & Donuts. To further please your appetite for thrifting, head over to Out of the Closet Vintage Boutique for an unbelievable selection of unique items from every decade. For an eccentric display of taxidermy, jewelry, and other goods, stop by Bones & Stones.

Drive into Roxbury to check in at the one-of-a-kind Roxbury Motel. This unique establishment is a creatively kitsch stay for the colorful and playful at heart. Rooms are inspired by various films and TV series from the ‘60s and ‘70s, providing a much-appreciated sense of whimsy and originality in the hospitality industry. Guests can stay in rooms themed after the likes of Wizard of Oz, Indiana Jones, and Gilligan’s Island.

Walk across the street to Public Restaurant & Lodge for a sense of the local environment. Panko-crusted fried goat cheese, grilled Atlantic Salmon, and four cheese tortellini make it a perfect place for dinner. It’s also great for some pre or post-dinner drinks with hot cider and other cocktails on the menu.

If you crave a bit of a more upscale scene for dinner, take a drive to Brushland Eating House in Bovina Center. The warm and intimate environment is located in a classic, three-story, colonial house. The menu offers the palate a comforting, yet rich aesthetic that complements the cozy environment. The cast iron chicken makes the perfect main course, with the brown butter blondie as a delectable dessert.

Day 3:

Enjoy a traditional pancake breakfast with a gourmet touch at Phoenicia Diner, a retro-chic eatery that opened in 1962, moving to Phoenicia in the ‘80s. Topped with fresh fruit, the pancakes are perfectly complemented with a glass of freshly-squeezed grapefruit juice. The beer-battered onion rings make for an irresistibly indulgent side dish.

Craving some good Catskills breakfast...

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Head to Belleayre Mountain for day two of your ski lessons. With 50 trails, parks, and glades, as well as eight ski lifts and four lodges it’s one of New York’s best skiing destinations. If you’re done with the physical part of the trip, hang around Stone and Cooper, a bar located in the Discovery Lodge with gorgeous views of the mountains.

After hitting the slopes, head back to the Roxbury to unwind. Onsite is the Shimmer Spa, where you can take a soothing dip in the hot tub or relax in the sauna. Wash it all away in a shower made of black river rock.

Before heading back to the city, stop at Wayside Cider for some locally brewed ciders and a hearty cheese and charcuterie board. Agriculturally inspired, the location is decorated with pieces of rural charm. During warmer months, the outdoor bar becomes a popular local venue with live music.

There’s no better way to recharge your batteries than with a picturesque Catskill weekend, before braving the remainder of another brutal New York City winter.


Glenn Garner

Glenn Garner is a southern boy, a Drag Race fan, and the love child of Paula Abdul and MC Skat Kat.

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