This Charming Catskills Ski Town Is Almost Unrecognizable—Here’s What’s New

Are we really in Windham?” my mom asked me for the third time that day. It was 7 p.m. on a Saturday last winter, and we were sitting in a corner booth at Babblers, a restaurant in the Wylder Windham hotel. The bar was packed with groups of friends in Canada Goose jackets and cashmere turtlenecks, laughing over martinis while a classic-rock cover band was getting ready to play.

Set about three hours north of New York City, the tiny hamlet of Windham, in the eastern Catskills, is often overlooked. At least, that was the narrative I grew up with. This is where my grandpa and his cat, Magic, lived in a log cabin; it’s where I would go to ski and shoot BB guns at cans a few times a year before returning home to the Boston suburbs.

For my mom, the story is a bit more convoluted. She was just five when her family moved to Windham from the Upper East Side. Her parents divorced three years later, and both remarried soon after. While she lived with her mom (first in Kingston, New York, then on Long Island), she visited her dad in Windham every other weekend. She rode ATVs with her brothers and taught her five half-sisters how to ski. She knew everyone, and everyone knew her. 

From Left: The grounds of the Wylder Windham, in upstate New York; the library at the Henson hotel.

From Left: Wylder Windham; Jessica Olm

Last January, my mom and I were overdue for a vacation together, and Windham seemed like the perfect place. It’s between her home in Massachusetts and mine in New York City, she had never visited as a “tourist,” and I was eager to show her the new Windham I had heard about—a town that has, over the past decade, welcomed luxury hotels, fine dining restaurants, and, most recently, an exclusive members’ club. 

After picking me up from the Amtrak station in nearby Hudson, my mom drove the fadliar mountain roads, past trees white with a fresh layer of snow. “There it is!” she 
 exclaimed as we passed the town sign: welcome to windham est. 1798 “gem of the catskills.” Throughout the weekend, she would recognize little else.

On Main Street, the former national bank now houses Windham Local Public House, a restaurant that my aunt—who still teaches at the school across the street—says has great live music. A short drive down the road, we came across Gardenheir, a boutique selling high-quality gardening tools and apparel that opened in 2022. Objects on the artfully arranged shelves included work jackets, French clogs, and watering cans—the latter for the hefty price of $328.

From Left: Amish chicken at the Henson’s Matilda restaurant; the Gardenheir store.

From Left: The Henson; Gardenheir

We checked in to Wylder Windham. Like many of the newer businesses in town, the Wylder replaced a longtime staple my mom knew well, the family-run Thompson House hotel. The new property has 110 rooms spread across seven Victorian buildings, all a short walk from one another. I sipped my welcome drink—a hot toddy—while observing a stream of families in ski gear stumble into the main lodge, fresh off the shuttle. 

That night at Babblers, we were surprised by the party-like atmosphere. Chatter from diners was reverberating around the room, and it took 15 minutes to get seated. My mom and I barely spoke over dinner—we just listened to the music, enjoyed our French onion soup and roast chicken, and took it all in.

In the morning, after much-needed croissants and coffee from Babblers Bakery, we went to the Windham Mountain Club—the newest and perhaps greatest force of change to hit the area. In 2024, the formerly public Windham Mountain, where I learned to ski, was rebranded as a semi-private resort—with a buy-in of $200,000 and annual dues of $15,000. (It’s the latest venture from Sandy Beall, cofounder of the revered Blackberry Farm and Blackberry Mountain in Tennessee.) 

While the public can still purchase day or season passes, the transition has spurred some backlash in Windham. The family-friendly mountain had always appealed to everyday skiers; now it caters to wealthy New Yorkers (Blade offers helicopter service from Manhattan). An aquatic and racquet center are coming soon, and the 18-hole golf course—which opened to the public in 1927—will be updated in stages over the next few years.

The lobby of the Wylder.

Wylder Windham

Having not skied in a decade, I had forgotten what it felt like: the anxiety in my gut as I strapped on the chunky boots, the crisp air entering my chest as I reached the top of the mountain. Unlike my mom, I was never a good skier, and being so out of practice, I feared the worst. But after a few slow and steady runs, I realized I was actually having fun. 

Stress levels were tempered by the perks, too. We were treated to membership benefits at the Mountain Club, which gave us access to priority lift lines, a private locker room, and a restaurant called the Grill, which has fireplaces and a clear view of the trails. Halfway down the slopes, we stopped for lunch at Cin Cin!—another members-only restaurant, which is modeled on a chalet in the Dolomites. The calamari, handmade pappardelle with Bolognese, and bold red Italian wine matched the caliber of the design (and made my ride back down the mountain all the more thrilling).

Weary from our ski day, we relocated to the 16-room Henson, a hotel that opened in May 2024 and is housed in a restored late-19th-century building. Inside, the cedar paneling and smell of burning wood created an immediate aura of calm. After we’d freshened up in our farmhouse-modern room, I selected The Diaries of Franz Kafka from the library, then planted myself by the fire in the common living room.

A corner booth at Matilda.

Jessica Olm

Matilda, the hotel restaurant, was just as inviting. “If there’s something on the menu that seems strange to you, order it,” our waiter said. I chose the tuna belly with nasturtium (an edible flowering plant, I learned) and the hay-aged duck. Both were complex and exquisite—dishes that I never expected to find in a place like Windham. 

We were in no hurry to leave the next day, so we spent the morning exploring the back roads of my mom’s youth. We headed to Larsen Drive—named after my grandpa, Gordon Larsen, who lived at the top of the hill in the late 1980s. At every street corner, she listed names of childhood friends, not knowing where they are now, but vividly recalling what they were like then. 

Our last stop, the Catskill Mountain Country Store & Restaurant, was my childhood favorite. Its shelves are still filled with local goods like mugs and honey sticks. The diner still serves classics, like a roast-beef sandwich. As I was browsing, I overheard my mom chatting with one of the waitresses, who lit up at the mention of my grandpa. “Gordon? He came here every morning!” the woman said. It was a nice reminder that Windham may still be, after all, just a tiny ski town in the Catskills. 

A version of this story first appeared in the December 2025 issue of Travel + Leisure under the headline “Winter Warmer.”