New York's Catskill Mountains Get a New Hotel with Outdoor Fire Pits, Stunning Antiques, and the Best Strawberry Rhubarb Pie

New York's Catskill Mountains Get a New Hotel with Outdoor Fire Pits, Stunning Antiques, and the Best Strawberry Rhubarb Pie
Courtesy of Wylder Hotel Windham

The Wyndham Wilder hotel, which opened its doors in July 2022, is under the spotlight as Rich Report takes a closer look.

Since I was a child, I have driven up to Windham, a small town in the Catskill Mountains of New York. I usually turn right off New York State Route 23, toward my family's house. But this time, I turned left. That's because I decided to stay at the Wylder Windham hotel instead of staying with my parents, since it was renovated extensively and opened in July.

After crossing the small bridge over Batavia Kill's rock-strewn stream and driving up to the two-story white clapboard main lodge, I could instantly see the transformation was going to be spectacular. 

Since 1880, the hotel has been in operation, and thankfully, much of its historic charm has been preserved thanks to the renovation. After a three-hour drive from New York City, the wide-planked oak floors complement antique golden yellow couches flanking an inviting fireplace, making for the ideal spot to relax. 

It would have been impossible for me not to play a round of backgammon with a glass of something strong next to the fireplace, which is a beautifully restored heirloom backgammon set. Every shelf in the lobby is lined with old books — some purchased, some found during the renovation — giving it a warmth that only aging pages can provide. 

Courtesy of Wylder Hotel Windham

After settling in my room with a red rug and purposefully mismatched furniture, I sat on the balcony in one of the Adirondack chairs and took a breath. Leaving NYC, I was mesmerized by the carved ski runs at Windham Mountain and the lush greenery that can only be found outside the city. I gazed down at the heated pool and up at the surrounding mountains.

The setting was quiet and comfortable. That's exactly what John Flannigan, founder and CEO of Wylder Hotels, was looking for.


Courtesy of Wylder Hotel Windham

"It felt whimsical, yet really familiar," Flannigan, who grew up in upstate New York himself, shared. "It reminded me of childhood places I've been with my parents." 

A total of 110 rooms are spread out across seven buildings, and by October, all of them had been opened for guests. With 20 acres of nostalgic amenities, the property is sure to take you back to a time when screens were not around: wood-fired saunas, fire pits, pickleball courts, cornhole boards, and the (free) Ms. Pac-Man arcade game in the rec room, a Land Rover Defender 110 restored, hammocks surrounded by trees overlooking the creek and mountains.

Courtesy of Wylder Hotel Windham

"It's about nature, and it's about activating it in a way that feels natural," Flannigan said. "I think sitting in an Adirondack chair next to a streaming river without hearing car noises is divine. We try to give those experiences to people."

The creek was slowly flowing through town as the water twisted and swirled around the rocks. Following Flannigan's advice, I went down the hill outside the property and crossed over the grass to find it. The Windham Path is 1.5 miles long and has wildflowers, a covered bridge, and a rambling water as a soundtrack. It's the perfect setting in a place like Windham.

When you want to escape the city, Windham is a sleepy town. As well as putting me in a central location in the town, I was also surrounded by quirky jewelry shops selling ski pendant necklaces and quilt shops featuring floor-to-ceiling color, along with an absolutely thriving food scene.

A short walk over the creek brought me to Union and Post, where I listened to live music and sip a Ski Bum cocktail made with tequila, pomegranate liqueur, lime, agave, and cinnamon. You can also go to the Deer Mountain Inn restaurant nearby for a romantic evening, which has just enough candlelight and serves simple food that comes straight from the hotel's garden or is sourced from local farms.

Besides shopping and dining, here's plenty to do. In the winter, you can ski, and in the summer, you can ride Windham Mountain's scenic chairlift. But one of the best ways to spend the day is to take a wine flight at The Vineyard at Windham, a small winery nestled in rolling hills just outside of town. It is the perfect place to sit on the patio, enjoy olives and fruit, and enjoy a glass of your choice. 

Courtesy of Wylder Hotel Windham

Back at the Wylder, I went to the hotel's restaurant Babblers, which combines the traditional with the innovative (think blistered shishito peppers with cilantro lime crème fraîche, which my sister tried to replicate at home, but failed to do so). I ate every last flaky crumb of the strawberry rhubarb pie that the restaurant's bakery made, along with homemade vanilla soft serve, with almost embarrassing pleasure. 

It's a modern property throughout, but it embraces its past and knows exactly where it came from. The pie was simple, nostalgic, and perfectly executed.

The cost of a room varies according to the season, but starts at $215 per night. 

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