Off the Beaten Path: The Wylder Hotel Tilghman Island
There’s no such thing as a shortcut to Tilghman Island. To get there, you must wind your way through Talbot County on Maryland’s Eastern Shore—passing the bustling hubs of Easton and St. Michaels, and the quiet hamlets of Claiborne and Wittman—to what feels like the end of the earth. Eventually, you come to the old drawbridge and cross over the Knapps Narrows onto this spit of tidewater. It takes a while, but once you’ve arrived, time seems to slow down and even tempt you to stay, especially if you’re posted up past the tackle shop and fire hall at the new Wylder Hotel.
Located in the historic Harrison’s Chesapeake House, which closed last October, this new boutique resort is a sea change for the tiny town—population 892, give or take. Over the past few years, this watermen’s community has started to experience the slow roll of gentrification, with wedding groups flocking for the sweeping views, McMansions sprouting up on the smooth terrain, and its surrounding county being crowned the “New Hamptons.”
Since opening in April, the Wylder, with its nostalgic, nautical-chic vibes, might be the hippest hotel on the entire Eastern Shore—consider it the cool kid sister to the fancy Inn at Perry Cabin—bringing trendy touches, modern amenities, and a fresh coat of paint to its historic structures, which were first built as a boarding house in 1898.
“We wanted to honor what was here,” says John Flannigan, CEO of the new Wylder Hotels brand, which he launched with this location after years of opening boutique lodgings such as The Ace Hotel in New York. “Tilghman has good vibes and a lot of soul and the property is beautiful. To me, it was a no-brainer. We aren’t trying to be the Hamptons; we’re just trying to be a charming, updated, contemporary version of the Chesapeake Bay.”
Along nine acres of waterfront, every inch of the Wylder has been dedicated to rest and recreation. As you pull into the gravel driveway, you’re greeted by a fleet of black and white beach cruisers, ready for a morning jaunt. On the front porch, vintage-style beach chairs beckon you to recline in the afternoon breeze. To your right, a rope swing hangs from the limb of a giant silver maple, and to your left, the kitchen’s vegetable garden soaks up the sun—its herbs, lettuces, and tomatoes waiting to be served at your next meal. There’s a bocce ball court, a heated saltwater pool, standup paddleboards, and kayaks for leisurely exercise. The hotel’s 54 rooms, from waterfront suites to summer-camp bungalows, also come with Egyptian cotton linens, bedside tablets, and in-room spa services.
Of course, no respite would be complete without the accompaniment of a gourmet meal, and chef Sean Wheaton, formerly of the Think Food Group by Michelin-starred restaurateur José Andrés in Washington, D.C., has guests covered with two on-site restaurants offering both downhome and upscale cuisine with an emphasis on seasonal eating.
“I’m not trying to be the next Woodberry Kitchen but I want to serve asparagus when it’s in season; and when it’s available, I want to get it from the farmer up the road,” says Wheaton.
At Tickler’s, a classic Chesapeake Bay seafood house, diners can belly up inside at the boat-hulled oyster bar or crack into crustaceans on the casual outdoor crab deck. Whatever the weather, the al fresco seating is a must, with a slight breeze off the Choptank River, the occasional live music act, and a laidback beach bar hawking craft cocktails— like a refreshing watermelon margarita or a revamped rock-and-rum, made with local Lyon Distilling spirits from nearby St. Michaels—plus fine wines and regional beers.
With hip takes on old-school eats, Tickler’s menu encourages you to explore the Chesapeake’s bounty, with raw bar beauties like succulent oysters, harvested just up the street, as well as steamed standouts, such as spicy peel-and-eat shrimp and local crabs by the piece or dozen. Landlubbers can also indulge in an array of savory sandwiches, including a juicy Roseda beef burger, made with meat from Monkton, and the flavorful fried chicken sandwich, topped with crunchy coleslaw and pickles.
Meanwhile, Bar Mumbo, located inside adjacent to the hotel lobby, offers a more refined dinner option. With wooden captain’s chairs, antique oil paintings, and aquamarine accents, this fisherman-inspired pub makes the perfect setting for a salty-dog sailor’s crowd (though it’s more likely to host hipsters in board shorts and Ray Bans).
Mumbo’s menu is an ode to Tilghman’s maritime heritage, with buttermilk fried oysters and wild rockfish tipping a hat to the watermen who still ply the local tides today, while inventive dishes— chicharones, aka crispy pork skins with a smoky eggplant mousse; free-range chicken thighs, pan-seared with a medley of slow-cooked mushrooms and mustard jus—follow the rising trends of international influence and farm-to-table sourcing. “It’s comfort food, relevant to the area, but a little dressed up,” says Wheaton.
The Wylder’s restaurants are a welcome addition to the shore’s culinary landscape, where many restaurants— and menus—haven’t changed for years, if not decades. The hotel manages to pay homage to the region’s past while also looking toward the future. The team is especially excited for fall, when the wild oysters come back, the autumn foliage reaches its peak, and the renowned Waterfowl Festival returns, bringing thousands of wildlife lovers to the region in celebration of its roots.
Flannigan plans to keep adding to the hotel’s attractions—everything from fishing charters and sea duck hunting to pop-up shops and yoga retreats. “We’re on the first story of a 10-story building,” he says. “There’s so much more to do.”
But for now, it’s still a best-kept Eastern Shore secret, a world away from the homes of those D.C. and New York license plates that line the parking lot each weekend. “We’re excited to be here,” says Wheaton, “and we’re excited to remind the world about Tilghman Island.”
Wylder Hotel on Tilghman Island, 21551 Chesapeake House Drive, Tilghman Island, Maryland; 877.818.1922; Facebook and Instagram
