Boutique Design Events and Trade Fairs

Seeking to introduce its guests to all-season escapes in unexpected destinations, Wylder Hotels’ two current properties are ideal for the outdoorsperson. Wylder Tilghman Island, set on a three-mile island on the Chesapeake Bay in Maryland, and the recently opened Wylder Hope Valley, situated in California’s Sierra Nevada mountains feature all the trappings of modern luxury with zero snobbery.

A hospitality veteran with more than two decades’ worth of experience under his belt, including stints at Wyndham, the then-newly launched Ace in New York, and as COO of Proper Hotels, “I always knew I wanted to do my own thing eventually in remote, unexpected destinations,” says Wylder founder John Flannigan. “When I met my now business partner Chet Pipkin, we really hit it off. We were both big outdoorsmen, and the rest is history.”


When envisioning the concept for Wylder Hotels, which they founded in 2016, Flannigan and Pipkin (who is also CEO of electronics giant Belkin) were inspired by living in big cities and watching hotel investment capital tied up in chasing downtown urban locations. “I kept thinking, what about the distant, remote places?” says Flannigan. “I was so drawn to open space and road trip destinations, and on the business side no one was really doing it and scaling in the way I imagined it could be done.”

Wylder Hope Valley is truly a magical place with a storybook history. It was originally owned by the Sorensen family, who bought the property in 1899 and started renting cabins in 1926 (starting at 75 cents per night). Eventually it was purchased by an accomplished Swedish doctor, Johan Hultin, who sold it in the 1980s to a politically minded Santa Cruz power couple, the Brissendens, from whom Flannigan and Pipkin purchased the property.


“The Sorensen family is so integrated in the local history around here and it was a big part of our mission to preserve their legacy as well as the resort’s other former stewards,” Flannigan explains. Wylder has taken great pains to restore the work of former owners, but has also added elements like seven custom yurts with woodburning stoves and breakfast nooks, and a restored 1951 Airstream trailer complete with outdoor patio.

Designed in partnership with Portland, Oregon-based branding firm OMFGCO and with help from Sierra Sustainable Builders to source all local, natural materials, the approach allows the setting to be the star. The property offers 30 different cabins that have been individually and uniquely designed and built over the years, from cozy bungalows to spacious homesteads fit for families. Some feature sun decks overlooking the Aspen-dotted hillside. One, aptly called Norway House, was imported from the Scandinavian country by the previous owner, while a couple of the structures came from Santa’s Village in Santa Cruz.

“I kept thinking, what about the distant, remote places?” – John Flannigan, founder, Wylder Hotels

“I like surprising people,” adds Flannigan. “If you have never been to Wylder Hope Valley or Tilghman Island before and have no context going in, both places would be surprising to you in the best possible way.”

Photos: Ren Fuller