There are few places more charming than the Catskills. Located in southeastern New York, the area is only a two- to three-hour drive from NYC, depending on how far north you venture. I’ve explored a lot of the region during my 16 years living in Brooklyn, and although there are so many towns and areas I love, Windham is truly one of my favorites.
Situated in Greene County, Windham is known for snow sports, but there is so much more to the town than skiing and snowboarding. It’s a year-round destination with plenty of hiking and swimming, and it’s home to some of my favorite restaurants. Even if you don’t live in New York City, this beautiful mountain town is worthy of your attention. Here’s everything to see, do and eat in Windham, New York.
Things to Do and See in Windham
I’m trying to become a better skier, so a day on the slopes at Windham Mountain Club was the main event of my weekend. I booked a two-hour private lesson and was paired with Charlotte, who is an absolutely incredible instructor (and a bona fide local celebrity — everyone in town knows and loves her!). With her guidance, I was able to ski my first two green runs. The weekend was warm for March — it was 55 degrees on the mountain the day we were there. But Windham’s snowmaking program is excellent. While it was a bit slushy, it never got icy; even my husband, who learned to snowboard in the much fluffier powder out west, was impressed. As expected, après ski was a party, complete with an outdoor bar and live DJ.
In addition to snow sports, Windham Mountain Club offers all types of year-round activities, including hiking, mountain biking, fly fishing, skeet shooting, horseback riding and golf. While certain spaces of the club are members-only, if you stay at the on-site lodging, you’ll have access to things like the spa, gym and The Grill restaurant.
The Windham Path is a stunning, dog-friendly 1.5-mile nature walk that’s perfect for experiencing in any season. If you’re looking for a more difficult hike, Windham High Peak is a 6.8-mile trail with gorgeous views and ample bird watching opportunities. When summer rolls around, there are plenty of beautiful lakes with sandy beaches, including CD Lane Park and Colgate Lake.
Windham has a lovely walkable main street that’s lined with local restaurants and shops; Catskill Mountain Country Store is a favorite for locally-made pickles and jams, plus other fun souvenirs. A quick turn on NY-296 will get you to Gardenheir, an idyllic shop with the chicest gardening clothes and tools you’ll ever see. A few doors down, Briars & Brambles Books has a well-curated selection of reads with the best shelf talkers. Strike up a convo with owner Jen or one of the other helpful booksellers if you need a recommendation. If you’re looking for gourmet provisions, Paracasa is a perfect place to stop for cheese and charcuterie, local fish and meat, small-batch condiments, and coffee and tea.
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Where to Eat and Drink in Windham
Even if you’re not staying at The Henson (more on that later), you must have dinner at Matilda. Helmed by chefs Jeremiah Stone and Fabián von Hauske Valtierra of New York City’s Bar Contra and Wildair, the food is exactly as good as you’d expect from two critically-acclaimed restaurateurs. Matilda’s house-cultured butter is hands-down the best butter I’ve ever tasted, and every other guest I talked to at breakfast agreed. Also, don’t miss the lentils with tête de cochon, walnut and smoked gouda; Hudson Valley trout with clams, potatoes and green garlic; and the côte de cochon with broccoli di cicco and sauce moutarde. The wine list is superb, but pay Pat and Kathleen a visit in the bar next door to the dining room. This bartending duo is incredibly cool and creative, with drinks like the Hey Jealousy, made with gin, apricot, pisco and dry vermouth.
Millrock is one of my favorite restaurants in Windham. The staff is always so friendly, and the food is excellent. You can’t go wrong with pasta or pizza, but also pay attention to the specials. On my last visit, I had a great veal dish in a lemon butter sauce with broccoli rabe. The Windham Local is an excellent spot for breakfast or lunch. Their menu is a mix of American and Thai classics; try the pork soup dumplings and hearty chef’s salad. Prominence is a great Italian American steakhouse with a lively bar scene. And be sure to stop by Eastwind’s Bunkhouse Lounge for beautiful views and a nice classic cocktail.
Where to Stay in Windham
As mentioned above, you have to stop by The Henson, if only to eat at Matilda. But it’s also one of the best places to stay in the area. The hotel is dog-friendly, which is always a plus for driving-distance destinations, and my Goldendoodle Spaghetti loved the big fenced-in yard where he could run and play with other four-legged guests. The design of the property is just beautiful — I loved our room’s warm, inviting tones, and the common living area is awash in natural light and features a wood-burning fireplace. I already talked about how great restaurant Matilda is, and the breakfast is just as spectacular. There’s also a private wellness room you can book by the hour, which includes a sizable workout space and infrared sauna. And the staff is great. They helped us with area recommendations and connected us with Dawn 2 Dusk Car Service when we needed a ride one night.
While The Henson is located in a charming hamlet about a six-minute drive from Windham proper, Wylder Windham is closer to the action. While there are quite a few warm-weather amenities we weren’t able to use, the property is absolutely full of them — it has a heated pool, wood-fired saunas, pickleball courts and a dog run (yes, Wylder is also dog-friendly). But the downstairs game room was where we spent a lot of our time; it features a pool table, ping pong, cornhole and arcade games. We stayed in the main house and had a very sizable room with a sitting area and private balcony. On-property restaurant Babblers is open for lunch and dinner (and is quite delicious), but the hotel doesn’t serve a proper breakfast (but complimentary coffee and pastries are available in the morning).
Editor’s note: After accepting the Ikon Pass for years, Windham Mountain will not be one of its destinations for the 2025/2026 season. I talked to a lot of people during my trip, and no one is happy about the change. Locals are nervous that it will reduce tourism, and those who have traveled to Windham yearly to ski on the Ikon Pass are devastated that the mountain is no longer included. That said, there’s no better time to visit and support this amazing little town. Go take ski and snowboard lessons from the knowledgeable instructors. Book a couple nights at one of the independent hotels in the area. And remember there are amazing nature adventures to be had in every season, plus excellent restaurants and shops that are open year-round.
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