Great hospitality is showing, not telling. When I arrive at Eastwind Hotel in Windham, NY, it’s well after dark, rush-hour traffic ballooning a two-hour, 45-minute drive from Brooklyn closer to four. I belly up to the bar at the Bunk House Lounge to check in and my eyes immediately fix on a guest’s bowl of fettuccine Alfredo. It doesn’t go unnoticed.
“You want some?” He asks.
A storm had just passed through, plummeting temps into the teens. A neat row of icicles festooned the hotel’s gutters and the trees, with a fresh dusting of snow, looked like Frosted Mini-Wheats. Pasta and a glass of red wine is the culinary cure-all for spent nerves, winter blues—well, pretty much anything. There was only one right answer.
“Absolutely,” I say.
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I have an inkling this isn’t just another guest when he goes straight into the kitchen and returns with a bowl. Turns out the man of the hour is Bjorn Boyer, co-owner of Eastwind Hotels. And he isn’t doling out leftover pasta from the hotel’s supper service (which I learn is only available Fridays and Saturdays; I’m here on a Monday). He’s sharing his own dinner, made from scratch.
We sit across from one another, elbows planted on the bar top, and discuss the origins of the Windham property. A sip of pinot noir, a twirl of fettuccine—the tension of the day unfurls, replaced by a quiet calm. And I haven’t even seen my room yet.
Eastwind Hotel — Windham: Past and Present
Currently, Eastwind Hotels has boutique properties in Windham, Lake Placid, and Oliverea Valley (its newest). Here at Windham, the eponymous mountain range serves as its playground. In 2018, Boyer purchased and converted a 1920s-era bunkhouse used by hunters, fly-fishermen, and outdoor enthusiasts with two partners, his wife, Julija Stoliarova, and Dan Cipriani (of Brooklyn’s Sea Wolf).
Eastwind Windham isn’t a timber-clad cabin with taxidermy animals and buffalo plaid. It has a more discerning traveler in mind. The aesthetic has a strong Scandinavian backbone with elements of mid-century modern design. The glamping cabins and suites even maintain some of the existing materials from the bunkhouse, like hardwood flooring.
“When designing each of the Eastwind properties, we pulled inspiration from the history of their respective locations and incorporated elements paying homage to local flora and fauna,” Julija Stoliarova says.
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She and Bjorn grew up exploring the Scandinavian forest, and that whimsy carries through. For example, rooms have framed photos of wildflowers and plants, and books of classic children’s literature depicting adventures like Rip Van Winkle and Other Stories and All the Mowgli Stories to reinforce a spirit of wonder.
“We were drawn to Scandinavian design as its pillars are simplicity and functionality, and inspired by the Swedish word lagom, meaning ‘just right,’ as it allows for minimalism and subtle decor to complement the serenity of the outdoors,” she adds.
Accommodations at Eastwind Hotel — Windham
In total, there are 16 rooms and 10 cabins—many of which are pet-friendly. For my two-night stay, I’m in a Lushna Suite, a freestanding cabin with a lofted queen bed dressed with Frette bedding and a navy-and-cream Faribault wool blanket. It’s a brilliant option for working remotely should you visit during the week, as it has a writer’s nook that doubles as a mud room for slushy boots. The 400-square-foot cabin has a living area with a pull-out sofa and warm yet modern touches like a leather pouf ottoman, a Persian-style rug, and a woven basket light fixture. A green-tiled en-suite bathroom completes the space with an adjacent linens cubby stocked with towels and colorful Pendelton ponchos to make snowy treks to the property’s two wood saunas.
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Triple doors open entirely to take advantage of the private deck, hammock, and outdoor shower in the warmer months, but in the dead of winter it’s all eyes on the fire pit. If you ring the Bunkhouse Lounge, they’ll light it and bring a basket of s’mores supplies and even mulled wine. Of course you can also enjoy the main lounge’s communal space. Settle into a chair by the fireplace for a nightcap (highly recommend the Old Forester negroni) and a game of chess.
One thing you won’t find on the property: TVs. It’s a deliberate choice—encouraging guests to unplug and relish the presence of nature and whomever they happen to be traveling with.
Other spacious lodging choices include Eastwind’s Suite, 600-square-foot spaces amenable for up to four guests—perfect for families. There’s a seating area that juts up to a wood-burning fireplace. In the bathroom, thoughtful touches include a rainfall shower head and farmhouse sink. Hill House Double Queenand Hill House King (with a sleeper sofa) can also accommodate four guests, but are a bit more snug at 400 square feet.
If you’re traveling solo or with a partner, the Kingis a solid choice at 250 square feet. It’s hallmarked by a black-and-white color scheme with playful embellishments (think animal wallpaper adorning the built-in cubby storage and framed photos of mushroom varietals). The Writer’s Studio, located upstairs in the Bunk House, has the same square footage but boasts a desk with a typewriter (don’t worry, you can make room for your laptop) sure to get you in a flow space should this serve as your woodland writer’s retreat.
And for those who prefer to be one with nature, the Lushna Cabinsare classic A-frames with queen size beds positioned under a triangular window to peer out at the landscape.
What to do at Eastwind Windham
You can start your morning slow and have a breakfast basket delivered to your room. It’s available all week from 8 to 10:30 a.m. and comes with a medley of croissants, parfaits, eggs, jam, fruit, coffee, and tea. If you like to be active come first light, head to The Windham Path, a 1.5-mile-long loop off Route 23 (half a mile from the hotel) that’s arguably more beautiful after a storm—when ice crystallizes over the branches and trees.
You can run it as a there-and-back instead of a loop to make it a three-mile route, or simply walk along for a leisurely stroll. Eastwind has Hunter boots and snowshoes if it’s muddy or the snow is deep. You can even stash your gear in the hotel’s Ski Room if you’re using this as a basecamp for snowboarding or skiing at Windham Mountain.
Hikers should seek out Kaaterskill Falls, 15 miles from Eastwind, as the scenic two-stage waterfall tends to freeze over, leaving its usually thundering cascade frozen in time. It’s arguably better to come here in winter (especially during the week) as it gets busy with tourists in peak season. The hike itself is quick, just a mile-and-a-half, and easy to moderate depending on your fitness.
For something more challenging, try West Kill Mountain Trailin Hunter. The 6.5-mile out-and-back trail has some great lookout points—just be sure to bring crampons for your trail runners or hiking boots if there’s snow (snowshoes may even be necessary depending on the depth, so check the conditions and come prepared). Now that you’ve worked up an appetite, try some local favorites for breakfast and/or lunch.
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Best Places to Eat Breakfast and Lunch Near Eastwind Hotel — Windham
- Fellow Mountain Cafe: On Main Street in Hunter, Fellow boasts a menu of elevated hand-helds. Build your own breakfast sandwich or stroll in for lunch with options like roasted chicken salad with paprika aioli on sea salt focaccia or a roast beef melt with arugula, Swiss, and horseradish-onion aioli on sourdough. You can also get specialty beverages like golden turmeric lattes, matcha lattes, and mushroom-based MUD\WTR lattes.
- Shandaken Bake: A quick drive to Tannersville yields big dividends if you want hot coffee and a sweet treat. Try a butternut squash and olive oil muffin crowned with a crunchy molasses crumble or go for the bakery’s famed Chubby Squirrels: Apples are stewed in molasses and vanilla, then folded into a scone-coffee cake hybrid studded with cinnamon crumbs and orange zest.
- Gracie’s Luncheonette: If you’ve got a sweet tooth, do yourself a favor and get a half-dozen, dozen—actually just go straight for a baker’s dozen (13) and take a bite out of inventive flavors like Brown Butter Hazelnut Crunch (yeast donut), Pomegranate + Cardamom (yeast donut), Fluffernutter (filled donut), and Butterscotch Blondie Old Fashioned (cake donut; available on weekends only). There are plenty of classic diner eats like a tuna melt, fried green tomato BLT, and country fried steak and eggs should you want something savory.
- Phoenicia Diner: You’ll strike gold at this all-pleasing diner. It serves up buttermilk pancakes, smoked trout or lox on a Brooklyn bagel, and nearly a dozen gourmet spins on classic sandwiches (Oyster Mushroom Cubano, anyone?). It’s located in the town of Phoenicia, a village west of Woodstock, roughly 23 miles from Eastwind. If you’re trekking back to NYC, this is a great place to stop as it’s on your route home.
In the afternoon, warm up in one of the two dry saunas on Eastwind’s property, then relax in the main bunkhouse.
“Recently, we invited guests to join us for a guided whiskey tasting in our main bunkhouse and coming up we’re offering a hot chocolate bar,” Stoliarova says. In the future you can also expect candle-making classes where guests can create their own personalized scent.
Check the property’s “happenings” calendar to see what’s available during your stay. A Saturday itinerary may include an evening tarot card reading, live music in the lounge, then Saturday Supper. Guests will receive invitations for the prix fixe service ($65 per person) a few days prior to check-in and be required to make a reservation to join.
The menu changes each week, but always boasts seasonal ingredients and dishes served family-style (mains can include cabbage steak, Atlantic salmon, and red wine-braised short rib). On Friday and Saturday evenings, in-room beer, wine, and cocktail delivery goes until 9 p.m. The bar is also open to guests and non-guests Monday through Sunday from 5 to 10 p.m.
For dinner, you’ve got no shortage of incredible options. The hardest part is selecting where to try first…
Best Places to Eat Dinner Near Eastwind Hotel — Windham
- Tabla: For expertly made small plates with a Mediterranean flair and inventive signature cocktails, head to this neighborhood joint in Tannersville.
- Jessie’s Harvest House: Also in the neighboring village of Tannersville, this cozy spot serves up locally sourced American-style cuisine. You can get elevated comfort food like crispy Brussels sprouts smothered in local clover honey and banana vinegar; beef, veal, and pork meatballs (a family recipe); and Hudson Valley steelhead trout with butter beans.
- The Maker Restaurant: Encapsulated within a glass conservatory, this hotel’s restaurant celebrates community by showcasing ingredients from Hudson Valley farmers and purveyors. Enjoy duck breast and confit with celeriac and Asian pear, and olive oil cake paired with buttermilk ice cream and marcona almond for dessert.
- Wm Farmer & Sons: In Hudson, this rustic barroom and restaurant offers an upscale winter menu fit for a king. Share oysters, Burgundy snails, and beef tartare, but keep the smoked Berkshire pork shank ramen pot all to yourself.
- Prospect at Scribner’s: Just 10 miles away in Hunter is Scribner’s Lodge, whose restaurant is open on select days for brunch, lunch, dinner, and après-ski. It celebrates local cuisine with entrees such as rabbit, venison, and fowl stew; pressed chicken cooked with chardonnay and local mushrooms; and bone-in Berkshire pork schnitzel with aioli.
You’ll come to find your jaunt to the Catskills goes by in a flash. But here’s the beauty of local getaways (if you’re lucky enough to be local, that is): It urges you to explore your own backyard more—and pencil in your return faster than you can inhale a bowl of complimentary bowl of fettuccine Alfredo.
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