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The Weekender: The Catskills, New York

Rich in wildlife, culinary experiences, and snow-filled activities, it is no wonder New York’s finest are heading upstate

There’s a secret about the Catskills region of upstate New York that its own residents hope doesn’t get out too far: It’s about as good living as it gets. Don’t believe them? They’d prefer it to stay that way.

Tucked away two-and-a-half hours north of New York City, the Catskills have blossomed into a collection of picturesque, remote towns that have experienced their own kind of resurgence. The area provides locals and visitors alike the tastes and pleasures of the Big City, while still maintaining the rich wildlife it has always been celebrated for. While many conveniences of city life aren’t necessarily found here, there are plenty of reasons to unplug and head up to this oasis.

During the winter, a time during which most New Yorker’s dread the outdoors, there are still some of us that crave a breath of fresh air—just not amidst the high rises of Manhattan. Enter: the Catskills. Here, you can find the quintessential winter experience—yes, so much hygge—from roaring fireplaces and s’mores, to skiing that’s friendly for all levels, and luckily, all the trappings you love so very much. Including Shandaken Inn, a luxury bed and breakfast that promises to feel like a home away from home, a brewery that feels more new-age than Williamsburg, and drinking by the fire, below, find our perfect itinerary for a weekend in the Catskills.

Where to Stay:

Shandaken Inn, 1 Golf Course Rd, Shandaken, NY

Once you make your way upstate, check-in to Shandaken Inn. With 15 rooms and a modern aesthetic, the inn’s intimate feel makes for a pleasurable, luxurious stay. The decor skews more towards that of a tasteful home—something you might find in a Tour DuJour, rather than in Into the Wild. For that reason, every city person who truly considers themselves a ‘city person,’ for better or for worse, might actually come to fall in love with this particular stay. That’s not to say you won’t find what you’re looking for, if what you want is to truly feel one with the Catskills—Shandaken Inn finds a way to compromise.

Shandaken Inn

Feel like you’re a world away as you enjoy the property’s 12 private acres and amenities—Malin & Goetz bath products, a state-of-the-art fitness room with Peloton bikes, plenty of board games available by the inn’s bar, an indoor fireplace and outdoor firepit—and don’t worry about losing touch with reality, thanks to smart televisions in every guestroom and high speed WiFi. An attentive, small-but-mighty team takes care of your every need, whether it be a few hand-crafted cocktails and a delectable breakfast, or a personally-drawn map of the surrounding area in the case you’d like to head out and explore. The only thing that might tempt you to leave the premises might be a run down the bunny slopes.

Where to Ski:

Belleayre Mountain, 181 Galli Curci Rd, Highmount, NY

About a 10-minute drive from Shandaken Inn, consider taking your shredding skills to Belleayre Mountain. An up-and-coming mountain that’s seen a shift towards becoming the family-friendly mountain of choice upstate, Belleayre’s compelling quality might just be that—because it’s admittedly less of a go-to for visitors, the experience of skiing at this mountain is less one waiting on line, and more, well, skiing. Consider reaching out ahead of your experience to schedule lessons—from beginner to seasoned skier, Belleayre’s experts can head up to the highest peak with you to show you the ropes, or rather, runs.

The Shandaken

The Shandaken

Where to Eat:

Shandaken Inn, 1 Golf Course Rd, Shandaken, NY; Peekamoose Restaurant and Tap Room, 8373 NY-28, Big Indian, NY; Prospect, 13 Scribner Hollow Rd, Hunter, NY

Breakfast is a no-brainer on this itinerary—Shandaken Inn serves a mighty one—but for your other meals, primarily a good ol’ country dinner, consider taking a trip down the road to Peekamoose Restaurant and Tap Room. Let yourself get carried away by the restaurant’s quirky, downright-country decor—besides the many taxidermy’s, there also happens to be a chandelier made of tree branches—and make sure to order the butternut squash soup. If your weekend allows for another culinary run, also consider making the drive to Prospect. If the seared steelhead trout or 90 day dry aged ribeye doesn’t catch your eye, any of their handmade pastas definitely should.

Where to Drink:

Woodstock Brewing, 5581 NY-28, Phoenicia, NY; Peekamoose Restaurant and Tap Room, 8373 NY-28, Big Indian, NY

Woodstock Brewing

After dinner at Peekamoose, it’s worth a quick walk down the hall to the establishment’s bar. There, seats are in-demand and the cocktails are aplenty until midnight—if one was to say that there was “a scene” up in the Catskills, this would be where to find it. That being said, New York’s more forward-thinking set, dare one say the hipsters, have also set ground in the upstate area. One haunt that makes this clear is Woodstock Brewing, a restaurant and bar that serves its own supply of craft beer and was co-founded by a Wall Street transplant. Come for the beer and tasty bar nibbles, and stay for the Williamsburg-meets-Catskills vibe. In all the best ways, Woodstock Brewing provides locals, beer aficionados, and city folks alike a meeting-place to cheers.