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 will help 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.
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 ice cream 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 being 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.
The woman walks us through the restaurant, where a floor-to-ceiling window on the far end overlooks the firepit—”there was a fun group out there enjoying themselves last night,” she tells us—past an in-progress pool area, where she says they hope to incorporate a cold plunge section, toward our room. We’re staying in one of the brand’s “signature luxury cabins,” called a Lushna Suite, behind the main building. Inside, light wood panels extend from the floors up the walls and pitched ceilings. There’s a small working nook with a built-in desk and storage to the left of the entrance. The lounge space, which has very clearly been curated with outdoors-inspired decor, opens up to a spacious deck overlooking another grassy area. Across it, there’s another large building, similar in style to the lobby/restaurant, which we learn holds standard rooms and suites for guests not staying in the A-frame cabins.
3:30 p.m.: We climb up to our Lushna’s lofted sleeping area, which has just enough space for a queen mattress below a large triangular window that looks out to the trees. We decide to read for the next half hour until it’s time to get ready for our sauna session. My girlfriend, who never naps, in fact generally has trouble sleeping, dozes off for about 20 minutes.
4 p.m.: There are two robes hanging on wall hooks in our cabin’s green-tiled bathroom. We throw them on over our swimsuits (and under our long winter jackets) and run the couple hundred feet to the A-frame saunas on the other side of the property. Tonight, there are no other guests signed up for this time slot. We spend thirty minutes in each sauna—dry first, infrared second. On our way back, we pass the couple with the dog we’d seen earlier. I ask the dog’s name in passing—Sadie.
6 p.m.: Relaxed (and showered), we emerge from our cabin for dinner at Dandelion. Helmed by chefs Josh Bettencourt and Daniel Cipriani, the restaurant offers a seasonal menu and is open to both hotel guests and the public. We’re seated in a corner below the massive window that looks out to the firepit and hammocks. Near us, there’s a cozy fireplace area where a few people are enjoying drinks from the bar on a couch and stools. Across the room, I spot another dog (not Sadie!) sleeping under its owners’ dinner table like a Perfect Little Angel. It’s time to order: we opt for delicata squash with maple, honey, herbed goat cheese, and spiced pepita; ribeye with spicy broccoli rabe; and roasted eggplant with herbed cucumber tzatziki and farro tabbouleh. While we’re eating, I notice Sadie walk in with her owners.
I’d expected the hotel’s feel to be a bit more, influencer-y, if not for its branding and New York City proximity, then for its wellness offerings. Surprisingly, though, the crowd here seems more low-key than I imagined. There is, however, the woman at the table next to us who makes the (seemingly) older man across from her—relationship unclear—take multiple photos of her with arms outstretched between the pillars of the dining nook before their meal arrives. (The rest of the dinner they mostly sit in silence.)
8 p.m.: We try and lay in the hammocks for a bit, but it’s too cold to be outside and not by the fire, so we join a man who is already standing by it and slowly strike up a conversation. He’s from Romania, but isn’t visiting from there; he lives in Brooklyn’s Greenpoint, of course, with his wife and young daughter. We talk for a bit—about increasingly unaffordable rents in the city, the costs of raising kids there. Eventually, we head back to our cabin for the evening.
9 a.m.: We snag a booth at Phoenicia Diner just before the morning rush goes in full-swing, and order breakfast with eyes much bigger than our stomachs, but have little problem finishing it all. The air is brisk, and since the foliage has already fallen and the trees are bare and sad-looking, we decide we’d rather drive around to nearby towns and do more antique shopping than go hiking. Because we hadn’t planned our day before breakfast, we left Eastwind this morning without signing up for a sauna session to close out our visit. We decide to drive back—about 20 minutes on winding mountainous roads—to sign up for a slot in the afternoon. But the list is already much fuller today than it was yesterday when we arrived. We write our names down in a column next to another couple’s and hope for the best.
1:30 p.m.: It’s been at least an hour since we got to the sprawling Antique Warehouse in Hudson, and we haven’t stopped gawking at furniture and decor we can’t afford (nor would our apartment have room for). We do the same with the knitted clothes at the Nikki Chasin shop on Warren Street, and the homewares at Minna (though we can actually afford some of the inventory here, and leave with a lilac mug and woven basket), then start making our way back to Eastwind.
3 p.m.: Our plan is to have our final sauna session, then head home after our late checkout. As we’re pulling into the gravel driveway, ready to quickly change and hop into whichever one of the saunas the couple next to us on the sign-up sheet aren’t already occupying, we see Sadie and her owners walking in their robes toward the A-frames. We consider ditching our plan, feeling awkward about knocking on the sauna door, potentially disrupting their session, to coordinate a switch off. But, not wanting to pass up our final chance to sauna, I walk up the steps to the infrared one. Before I can knock, one of the pair opens the door, surprised by us as he exits. He says he and his partner actually planned to switch between the saunas in order to take turns watching Sadie.
It’s getting dark and it’s supposed to start raining, maybe snowing, on our 2.5-hour drive home, so we decide to cut our losses and head back to the city. Before, though, we add one detour to end the trip on a high note: Back to Fortunes Ice Cream for a glorious scoop to tide us over through winter hibernation.
Top photo by Lawrence Braun