The Nostalgic Charm of Upstate New York’s Wylder Windham

A picturesque escape, marrying small town comforts and elevated design

While walking around the small town of Windham in upstate New York, it’s easy to glance right over the town’s forthcoming resort Wylder Windham—and that is precisely the point. The Wylder’s Victorian architecture looks right at home alongside the early 19th-century buildings. Onlookers may never know the hotel boasts 20-acres, considering that its picnic and hammock-filled property beside the nearby Batavia Creek feels like public spaces. Yet the all-season destination offers seven different lodging experiences, views of the mountains and an easy way to explore the town’s outdoors and community; all of which combine for a charming and nostalgic stay.

Slated for a soft launch in mid-July and an official opening in August, Wylder Windham feels like it’s plucked from a bygone era because it partly was. As the third property from Wylder Hotels, who often transform storied properties into unique destinations, the Wyler Windham was renovated and reimagined from its previous life as The Thompson House, a family-owned and -operated resort established in 1880.

John Flannigan, founder of Wylder Hotels, saw the Thompson online in June of 2020 and immediately bought a plane ticket to go see it. When he did, he describes to COOL HUNTING, “I knew it was magical and made an offer the next day.” The Thompson was everything Flannigan looks for in his properties: characterful, heirloom and magnetic. “We’re always looking to honor and embrace what’s there,” he continues. “We’re certainly reimagining some spaces, but in terms of exterior architecture, we’re really honoring what was there and bringing it back.”

To do so, Flannigan kept elements of the Thompson, like the molding, stained-glass windowpanes, staircases and—to the delight of the Thompson’s previous residents who are already emailing to request specific suites they used to vacation in—the names of the rooms. With the help of local architect Jason Anderson, the Wylder’s new additions (including white oak wood that panels the floors and ceilings) still align with the hotel’s origins and help build the Wylder’s nostalgic experience.

Within the seven different lodges and its combined collection of 110 suites, the resort has an eye for luxury but not in a way that overshadows the surrounding nature. The goal, Flannigan explains, “is to try to make it look like its always been there and not overly designed. Most hotel designs I see out there are looking to make a statement in terms of being very design-y, and we’re just trying to make an instant classic.”

For its interior, the Wylder worked with Brooklyn-based design firm Post Company to create soulful and homey rooms. This means vintage rugs, burnt orange headboards, marbled bathrooms and large clawfoot tubs in the suites, extending the resort’s inviting yet unfussy atmosphere. The design also succeeds in striking a balance between the indoor and outdoor experience. In fact, out of the 110 rooms, 82 feature wide balconies with panoramic views of the mountain, the pool or Batavia Creek. From any room, a glimpse of Windham’s abounding surroundings awaits.

Thanks to the town’s proximity to Windham mountain, many think of it as ski destination, but the region—much like the hotel itself—offers so much more. Hiking on one of the many trails, golfing, mountain biking and fishing right in the Batavia are just some of the ways locals enjoy nature there. Wylder helps showcase the town’s many adventures with their carefully and minimally designed outdoor spaces. Picnic areas are strewn about the creek, highlighting and opening up access to the Batavia. A new pickleball field, open to residents and locals, offers another way to enjoy the outdoors. It’s easy to imagine families enjoying a field day in the court’s adjacent, open lawn where the Wylder also plans on hosting live music. Then, when guests are ready to wind down, the restored heated pool and sauna offer respite.

Every detail of the Wylder facilitates the ways tourists and locals enjoy exploring upstate. The resort’s dining options, Babbler’s Restaurant and Bakery, also reflect this. Though the head chefs are yet to be announced, the bakery will be structured as grab-and-go, offering American classics like strawberry rhubarb pie and soft serve ice cream, to make it easy for guests to pick up something before their hike or day outdoors. In similar fashion, the restaurant will serve comfort food using local and seasonal ingredients among an antique-designed setting.

For those looking to disconnect, get outdoors or enjoy the comforts of a small town community, Wylder is a charming reprieve from the city. Lying 35 minutes from the Hudson Amtrak station, it is both a convenient and cozy escape.

Images courtesy of Wylder Hotels