One Night in a New York City Getaway With A-Frame Cabins and Saunas

This story is part of Everyone Loves an A-Frame, our week-long celebration of simple structures with a cult following.

There’s a maxim among New York City residents that part of living in the city is thinking about moving out of the city. For the lucky ones for whom this actually just translates to buying a second home within driving distance, the Catskills, Hudson Valley, and further upstate regions have long provided a not-too-far-away refuge. (Hence the wildly competitive real estate market.) I myself am nowhere near being able to afford a second, let alone first, home. But I have become the type of New Yorker who likes to squeeze in at least one fall or winter trip north of the city, convincing myself that even one weekend of rural sweetness help will counteract the dreariness of cold, short days in the city. Because I am just one of many of this particular type of New Yorker, the region has experienced something of a hospitality boom in recent years, with a slew of boutique hotels and rentals that largely cater to city weekenders (increasingly to the dismay of locals). 

Even if you’ve narrowed your focus slightly, say, to one area: the Catskills, and know you want to stay in a boutique hotel over an Airbnb, choosing an accommodation can still be overwhelming, and I don’t just say that because I have ADHD and am a Libra. (I’m not huge on zodiac-based behavioral diagnoses, but the chronically indecisive trait does resonate.) In the Catskills alone, spots like Scribner’s Catskill Lodge, Piaule, and Urban Cowboy Lodge, though on a sliding scale of cost and luxuriousness, are all driving distance from quaint main streets of 20th-century villages (some lined largely with the same types of boutiques and wine shops you can find in gentrified Brooklyn), and as far as aesthetics go, pull from a similar bucket: Scandinavian, Japandi, or Americana-inspired mountain lodge. However, over the holidays, when my girlfriend prompted me about the possibility of a last-minute Catskills trip, Eastwind Oliverea Valley quickly and easily came to mind. The rates (ranging from around $250 to $530 per night, depending on room type) were within our budget if the hotel couldn’t comp our stay as a press visit, and we were both excited about the site’s A-frame cabins—and its wood-framed saunas. I reached out and, to our delight, the hotel agreed to host us for one night after Thanksgiving.

Saturday

9 a.m.: We’re on the road after a brief snafu with our Kyte rental car (the long and short is there was a miscommunication around the keys drop-off). Since check-in at Eastwind isn’t until 3 p.m., we’ve decided we’ll stop in a few towns on our way up to do some window shopping.

11:30 a.m.: Our first stop is Kingston; more specifically, Rough Draft, a coffee shop, bar, and bookstore in an old stone-and-wood building with massive windows that look out onto Kingston’s historic Four Corners. The place is pretty packed and there’s a bit of a line for the restroom; as I wait, I scan the fliers tacked on a large bulletin board—community book readings, film nights, queer dance parties. Admittedly, we mostly popped in to use the restroom, but the large, open space is filled with bookshelves and tables displaying all types of titles. We scan the selection for a while, and I’m tempted to try a pastry, fresh-baked from Rough Draft’s sister shop Kingston Bread + Bar, but I decide to just go with a coffee. 

We walk a block or two to Kingston Consignments, a tw0-level antique shop packed with everything from vintage furniture and decor (lamps, stools, homewares) to collector’s memorabilia (posters and figurines) and secondhand clothing. We find some great scores: a miniature wooden chair, a couple of records, and a pair of embroidered pants that I pulled off the rack as we were walking to the register and only eyeballed for size but, thankfully, fit well (which doesn’t always happen!) and are now among my most prized possessions. We stop at Moonburger, a "plant-based drive-thru burger joint," for a quick, in-car lunch, and it’s not long before I have my mind on ice cream. There’s a homemade, small-batch ice cream shop we’ve been to and loved in Tivoli—about 20 minutes north, and just across the Hudson—so we drive toward Fortunes Ice Cream.

1:30 p.m.: We scarf down our scoops and remark on the sign announcing the shop’s seasonal closure in a few weeks. (Fortunes, founded by a couple who met at nearby Bard more than a decade ago—one of whom eventually studied architecture at Columbia—shutters during winter.) We feel rather delighted by our good timing.

3 p.m.: Wanting to maximize our 24 hours at Eastwind, we arrive promptly for check-in. Pulling into the gravel driveway, there’s a large grassy area grounded by a firepit. Near it, a smattering of trees have hammocks hung between them. A collection of small dirt trails lead up to various A-frame cabins built into the hill overlooking it. We assume that the large black building with a slanted roof and wooden beams is where we should check in, because as we’re parking, we see another couple—presumably also millennials, and potentially also New Yorkers—walking in with their dog. I hadn’t realized Eastwind was dog-friendly (an oversight, based on their Instagram presence). I’m thrilled.

We’re greeted in the small lobby area by a really friendly woman who checks us in and walks us through the basics: we can book dinner at the hotel restaurant Dandelion (which comprises the rest of this building) on Resy; they start up a bonfire in the evenings, and we can grab blankets and s’mores kits from the lobby; and the two clipboards on the front desk are where we can sign up for turns in the on-site dry and infrared saunas. The sheets are organized by the hour, with two columns—"for when we’re really busy," the woman tells us—the idea behind that two guests (or groups of two, as the structures can accommodate) can sign up during the same time slots and switch off between the saunas when the hotel is super busy. There aren’t strict rules or oversight for this system, she tells us, but it normally works out without a problem. We sign up for an early evening sauna session and book a dinner reservation for shortly after.