Long before Men’s Journal called it a “dream town” in 1997, long before investors opened the first ski lodge on Cave Mountain (1963), Windham had earned its place as Gem of the Catskills—and the Thompson House, family-owned for its first 140 years, was undoubtedly a gem’s gem.
“I knew it was a Wylder the first time I saw it,” says John Flannigan of the Wylder resort group. It was love at first sight. “A river running through it, right next door to a ski resort and a golf course, massive oversized balconies—it was perfect.”
Flannigan, a veteran hotelier, founded his Wylder brand in 2016 to create “adventures—reimagined, restored classics in surprising locations.” Wylder Windham, purchased in June 2021 for $2.27 million, is his third project; taking its place with century-old refurbished resorts in the Sierra Nevada range and on Tilghman Island in the Chesapeake Bay. The 20-acre Windham property, with seven diverse Victorian lodges, had already won the love of generations of guests for comfort and deft hospitality.
“Windham’s a special place,” says Flannigan. “It’s got a great vibe; there’s a wonderful community downtown with delicious restaurants and intriguing retail. It’s a true all-season resort; besides the closest big mountain skiing to the metro area, there’s music and mountain biking. The country club is great. The resort itself has a storied past, but it was just starting to be past its useful life in some ways. It needed some tender loving care.”
The revitalization of the property, adding event spaces and modern amenities to the nostalgic summer-camp-for-grownups vibe that, it turns out, has been popular forever because it makes for a wonderful time, was welcome news to locals when the sale was first announced.
Eric and Debbie Goettsche, whose family has carried property’s hospitality torch since 1880, were seeking to retire after keeping the place thriving through the early pandemic with panache and were as glad to find a worthy buyer quickly as Flannigan was to discover the spot he describes as “magical.”
All eight buildings on the property have been renovated and refreshed by design firm Post Company, Montgomery-based architect Jason Anderson, and craftsmen from Poughkeepsie-based Baxter Built. Boutique comfort furnishings and high speed WiFi have been added to the 110 rooms and suites that comprise the resort’s various buildings: the Pines Inn, Tamarack Lodge, Manor, Spruce Cottage, Evergreen Lodge, Main Lodge, and Farmhouse. A restored vintage Land Rover Defender 110 Shuttle whisks guests to neighboring Windham Mountain for skiing in the winter and mountain biking in the summer, to the spectacular 18-hole golf course at Windham Country Club, or downtown to the picturesque, vibrant mountain town that Men’s Journal found “one of the wildest, tastiest, and smartest” back in ‘97.
On the Wylder Windham’s property itself, guests will find all the tried-and-true vacation classics. “We’ve got saunas, hammocks, a pickleball court, bocce. You can go tubing on the Batavia Kill. We have tree swings,” says Flannigan. “It’s really something special—whether they’re on a family vacation or a romantic couples’ getaway, I think people are just going to be amazed and delighted by what we’ve done here.” Other on-property amenities include rec rooms, a heated swimming pool and hot tub, firepits, and yoga and wellness programs. There are electric and pedal-driven bicycles available for explorers, and sleds for snowy weather.
There’s also Babblers Restaurant, famed for “delicious comfort food,” and Babblers Bakery, “beloved for its strawberry rhubarb pie and homemade croissants” according to Travel and Leisure magazine. Flannigan hopes Babblers will serve as a beloved dining destination for locals. “We’ll have beautiful outdoor dining by the river, classic comfort food, a lively cocktail program, fresh croissants and pies and soft serve ice cream and amazing coffee,” he says, “And I know from experience the value of having a place where locals love to go and we let the tourists in to join them. I hope we’ll play a key part in the ongoing revitalization of this community—hotel beds and event spaces are at a premium throughout the Catskills, and I think ours bring something really special to the perfect spot.”
A soft opening is scheduled for July, giving the public just a taste of the lobby, the lounge and some of the guest rooms; the resort kicks into high gear with overnight bookings in August. “I’m so excited,” says Flannigan. “We really think the restoration and the energy of the place will be well received. And we’re going to host a free concert series in the afternoons, with a great lineup —we want music to be a huge part of what happens here.”