Greene County Success Stories

Distance Destination Demand + Legacy Property Modernization = Wylder Windham

Distance Destination Demand + Legacy Property Modernization = Wylder Windham

As the hospitality industry continues to rebound from the pandemic downturn, more and more rural properties like the former Thompson House in Windham are getting serious consideration and investment from visionaries like John Flanagan – CEO and founder of Wylder Hotels. His company creates destinations for adventurers to escape the crowds, experience the outdoors, and enjoy all the modern amenities they demand.

Wylder Hotels are different. Their elegantly presented and highly approachable digital marketing describes them as “Brimming with character and sophistication. We exist for travelers who appreciate adventures, big and small. Storied locations. Modern luxury. Discerning taste. Discover destinations to disconnect and spend time with loved ones in nature.”

Properties John’s vision began with Hope Valley, just south of Lake Tahoe near the California-Nevada border, that features cabins, yurts, camping, and vintage spartan accommodations. Visitors fleeing the confines of communities in lock-down rapidly demonstrated that he was on to something.

Next came the Tilghman Island property on the Chesapeake in Maryland where “54 unique rooms range in size and style to fit your fancy. Enjoy sun-drenched waterfront views with outdoor seating and expansive porches in nearly every room. Dogs are welcome!” Wylder Hotel Tilghman Island sits on 9 acres of lush grounds and private waterfront property. Home to Tickler’s Crab Shack & Restaurant with a private 25 boat slip marina. Amenities include a heated saltwater pool, bocce court, beach cruisers to explore the island and lawn games a plenty.

Wylder then applied its model, mission, and vision to a longtime resort in the northern Catskills owned and operated for more than 140 years by generations of one family. The former Thompson House Resort is now called Wylder Windham.

In an interview with the Albany Business Journal, John Flannigan said the company was able to avoid the sharp decline in occupancy rates other hotels saw over the past two-plus years because its properties are focused on outdoor experiences with plenty of land, separate lodges and buildings.

In other words, social distancing was easy at the company’s resorts in California’s Sierra Nevada mountains and on Tilghman Island in Maryland when many people were seeking an escape from crowded metro areas.

“We did extremely well,” Flannigan said.

The pandemic obviously isn’t over, as evidenced by the growing spread of the latest strain of the coronavirus, but fears of traveling or being in crowded spaces have abated. Even so, the Wylder Windham offers the kind of getaway many want to experience.

Leveraging the success of their previous properties, and the availability of state & federal funding for job-creating businesses, the extensive re-making of the 20 acre Windham property began, and significant progress continued through last winter.

Progress of Exterior

Property HighlightsAt the Soft Opening on July 13th 2022, visitors toured and enjoyed:

  • Seven lodges, inns, manors, and cottages with a total of 110 rooms, including two- and three-bedroom suites with oak floors, custom furniture, and balconies with unobstructed views of Windham Mountain or the Batavia Kill
  • An oversized in-ground heated pool and a nostalgic recreation room with pool tables, shuffleboard, vintage arcade games, foosball, and more
  • Babblers, a restaurant and bakery
  • An expansive outdoor lawn with pickleball courts, hammocks, tree swings, fire pits, lawn games and live entertainment
  • Electric bikes, tubing, a wood-fired sauna, a hot tub, a dog run, and 4,000 square feet of indoor and outdoor event space

Two of the lodges have opened thus far, with a total of 29 rooms, along with the pool, bakery and most of the outdoor activities. Other amenities, such as the restaurant, will open soon.

“We’re going to be opening rooms constantly over the next two months,” Flannigan said, “and should be fully completed by the end of September with all 110 rooms. We are seeing huge demand in August, September and October. We’re very pleased with pre-bookings.”

Wylder Hotels bought the resort in June 2021 for $2.27 million, and according to documents filed with the Greene County Industrial Development Agency (IDA), the total project investment is over $20 million.

The new resort was expected to create 20 full-time equivalent jobs, but Flannigan said about 30 people have already been hired. Total staffing will exceed 50 once the resort is fully open.

Hiring has been challenging because of the tight labor market, but it’s easier to recruit workers for year-round, full-time hospitality jobs, Flannigan said.

If you want to learn more about how to Make It In Greene, check out our free helpful business guides and contact the Invest In Greene team by email or phone at 518-719-3290.

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Topics: Success Stories