Every weekend from December to March, a certain kind of New Yorker loads the Range Rover at a Tribeca garage and points it up the Thruway toward Greene County. For years, many of them pointed it at Windham Mountain, the friendly, family ski hill in the northern Catskills. Then Windham went private, rebranding as the Windham Mountain Club, where, per the Daily Gazette’s HudsonValley360, a family membership can cost more than $250,000 a year.
Now the club wants a hotel. And the town of Windham, a Greene County town of a couple thousand souls, is having the kind of fight that would be familiar to anyone who has ever attended a Manhattan community board meeting, with the addition of charcuterie.
Twenty-six rooms, $1,200 a night
The proposal is modest in size and immodest in price. The club has asked to amend its approved master plan to replace eight townhouses off Resort Drive with a 26-room boutique hotel and a four-bedroom villa, The Overlook reported. Club president Kristen Leach has said the hotel would be a “step above” existing luxury options, with rooms at $1,000 to $1,200 a night. The Mountain Eagle put the project’s cost at $25 million, with an opening marketed for 2028.
The slopes themselves remain open to the public under a 2025 development agreement with the town, but most of the club’s amenities, including its new Adventure Center, golf course and restaurant, are for members only, HudsonValley360 reports. The hotel, opponents fear, would deepen the divide: a resort for the members and their guests, in a town that runs on visitors.
The rival hotelier
The loudest of those opponents is John Flannigan, chief executive of Wylder Hotels, whose 99-room Wylder Windham sits on state Route 296. Flannigan has argued that Windham cannot absorb more lodging. In a July letter to the planning board, he wrote that the town runs at roughly 30 percent occupancy, against a national average of 62 percent per CoStar. He has been joined in letters by several other local hoteliers, including the proprietors of Albergo Allegria and Christman’s Windham House, The Overlook reported.
Flannigan has also escalated beyond letters. Earlier this month he posted a sign at his hotel reading “Fix Windham Planning Board Immediately: Fair. Transparent. Impartial. Lawful.” A full-page newspaper ad in the same language followed, according to HudsonValley360. On Thursday, Oct. 15, he hosted a town hall at the Wylder that drew about 50 people, seated at round tables with charcuterie boards and a wine selection, before the planning board’s own meeting across town. Flannigan addressed the crowd by video call.
The irony that the most vocal critic of a luxury hotel is the owner of a competing hotel has not been lost on anyone. Nor has the fact that he has a point about the process.
Recusals and a torn newspaper
Three planning board members, Claudia Lane, Michael Troccoli and Ray Curtis, have recused themselves because of ties to the club, The Overlook reported, leaving chair Lisa Jaeger, member Nate Holdridge and alternate John O’Neill as the only eligible voters. On Sept. 3, those three unanimously determined that no further environmental review was needed. A petition circulated by opponents objects that Jaeger and O’Neill had said on the record in August that they didn’t expect significant adverse effects before formally voting on that question, and asks whether the hotel should fall under a new town zoning law, The Mountain Eagle reported.
Critics, Flannigan among them, have also pointed to Jaeger’s role with the Windham Chamber of Commerce. The board’s attorney, Allyson Phillips, has said the board reviewed members’ ties to the club earlier this year and found that Jaeger’s did not meet the state’s legal standard for recusal. “I care about this community, and this weighs heavy on me,” Jaeger said Thursday, reading from a statement, per HudsonValley360.
Then there is the video. At an Oct. 8 town board meeting, Democratic supervisor candidate Connor Exum used public comment to bring up Flannigan’s newspaper ad. Town Supervisor Thomas Hoyt, his November opponent, ripped up a newspaper and tossed it at him, according to HudsonValley360, which ran a photograph. Hoyt later said he acted out of mounting frustration with Exum’s use of comment periods and acknowledged a moment of weakness. Exum’s video of the exchange has since circulated widely around town.
Where it stands
On Thursday, the planning board closed written public comment on the amendment. The board still has to decide whether the change meets the town’s legal standards, and Jaeger noted “a lot of work” remains for the board and the applicant. Leach, for her part, has denied the club is pre-selling rooms. “There is no way to book a hotel room now for that hotel,” she told The Overlook. “We’re very eager to get our shovels in the ground.”
Greene County Democratic co-chair Lori Torgerson, at Thursday’s town hall, framed it as a larger question. “My belief is that we need to have a serious discussion of the cumulative consequences for the community,” she said, per HudsonValley360.
Why the city should care
For New Yorkers, the Windham fight is the latest chapter in a story they helped write. The Catskills have spent a decade absorbing city money: boutique hotels, second homes, a ski club with a quarter-million-dollar family membership. Windham’s hotel question is really a question about whether the mountains remain a place weekenders visit or a place they own, and whether the local people who serve them still get a say.
Until the planning board rules, the slopes are still open to the public, and the Wylder still has rooms. Bring your own charcuterie.
The City Politic has reached out to the Windham Mountain Club, Wylder Hotels, the Town of Windham and the Windham Planning Board for comment and will update this story with any response.
Photo: Windham Mountain in 2008, before it became the Windham Mountain Club. tps12 / Wikimedia Commons, CC BY-SA 2.0.
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