Monday, August 4, 2025
By Annabel Taylor
As August melts into September, many Georgetowners are looking for a final summer getaway before autumn routines kick in. Twenty minutes southwest of St. Micheals, a lesser-known East Coast getaway lies down a gravel path—the stunning Wylder Hotel of Tilghman Island.
Kayaks and canoes available for guests by the bay. Photo by Annabel Taylor.
The 9.5-acre Talbot property was originally Harrison’s Chesapeake House, famous for hosting icons from the D.C. area since 1898, including Ronald Reagan, George Bush and Bill Clinton. Now the Wylder since its debut in 2018, the resort features 50 rooms with outdoor access, many opening right up to the bay and a host of amenities. Guests can enjoy kayaking, paddleboards and canoes as well as recreational activities like lying out on the private beach or participating in a game of bocce or corn hole.
Tickler’s Crab Shack and Restaurant. Photo by Annabel Taylor.
Wylder honors the balance that many hotels fail to accommodate—relaxation and adventure, all in one pretty package. The facade of the resort feels like the famed Inn at Perry Cabin’s relaxed southern cousin—white clapboard siding, a wooden swing hanging from an oak tree and a carefree breeze that trades refinery for barefoot adventures. The saltwater pool is a prime location and offers water aerobics every Saturday morning. Adjacent to the pool and overlooking the bay is the Scandinavian sauna and ice bath, providing a rejuvenating and detoxifying retreat. Guests can sign up for charter fishing and sunset cruises straight from the private marina.
Snag one of the bikes lined up by a hedge of white hydrangeas for a ride down to the Tilghman Island Country store for a quick bite, or the charming antique stores just steps from the end of the driveway. Tilghman Island reaps all the benefits of Talbot County minus the tourism and commercial distraction. Running 3 miles long with a population of 800, the island maintains its strong maritime culture and a vibrant watermen economy. Fourth generation islander Captain Alan Faulkner who wears many hats—waterman, firefighter and a renaissance man at the Wylder—spoke about teaching crab catching and oyster shucking at the resort.
Bikes available outside the front entrance. Photo by Annabel Taylor.
“A lot of these people, they’ve never shucked an oyster or ate one raw or caught a hard crab. Some don’t even know what color they’re supposed to be. The experience is showing people things, explaining about Tilghman the way it used to be. It’s a lot of fun,” he said with a grin.
Faulkner also gives “fireside chats” at the Wylder, a means to preserve the island’s rich heritage. He grew up on the Bar Neck of the island, where he reflects fondly on childhood memories of skating on the bay in the wintertime. Years of experience on the shore give him an almost mystic persona at the Wylder, a living link between past and present.
That same authenticity carried through to food. Tickler’s Crab Shack & Restaurant is the epicenter of the resort as well as a local favorite—neighbors on the bay can be seen pulling up for mid-day crabs by boat. With fresh food sourced daily from the docks and garden, the shack features a host of Maryland classics including cream of crab soup, Chincoteague oysters on the half shell and the iconic multi-layered Smith Island cake for dessert. The menu is creative and comforting all at once with its offerings of octopus ceviche and summer vegetable risotto. The crab cake dinner is a standout—expect a generous helping of lump crab and little breading. The restaurant is casual family fare, complete with bibs, mallets and a breathtaking view of the waterfront. Look forward to eastern shore hospitality and prepare with an angler’s appetite.
The panoramic waterfront sauna. Photo by Annabel Taylor.
A day here might look like a dip in the saltwater pool, followed by a kayaking adventure on the bay, a sweat-session in the sauna, a dinner of locally-sourced seafood—probably while being serenaded by a live Eagles cover—and s’mores by the bayside firepits to top it all off. But at the same time, you can find kids hosting lemonade stands along the road, a local farmer’s market across the street and the historic Watermen’s Musuem just half a mile north of the hotel. Guests will find the charm of the Wylder and Tilghman lies in its raw authenticity and honoring the history of the land, people and food that came before.