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Relax at the Wylder Hotel Tilghman Island, a secluded sanctuary on the Eastern Shore. (Image by Bill Whaley)

Take a break at this secluded seaside sanctuary on the Eastern Shore

When there’s talk of escaping to the Chesapeake Bay, bustling ports like Annapolis or St. Michaels get all the attention. But just 20 minutes from St. Michaels, there’s a peaceful Bayside town that has the charm of life on the shore, without as many pesky tourists.

Tilghman Island juts out into the Bay, making it a prime location for a robust population of watermen who still live and work there. It’s home to the largest remaining fleet of working skipjacks in North America.

Separated from the mainland by a narrow drawbridge, driving onto the island is like entering a different era. It’s only two hours from D.C., but things move noticeably slower, like the old-fashioned red-shingled country store and the Waterman’s Museum that only opens on the weekend.

Harrison’s Chesapeake House was once a mainstay of the island, where sports figures and politicians would vacation. The historic hotel eventually closed, but it returned in April, fully renovated and under new ownership, as a lifestyle resort: Wylder Hotel Tilghman Island.

One of a handful of places to stay on Tilghman Island, Wylder Hotel is an idyllic retreat perfect for a weekend away from reality. The nine-acre waterfront property has a quaint coastal vibe, with 54 guest rooms, enviable views of the Bay, a salt water swimming pool, lush lawns, boat slips, bikes, water equipment, and two dining options.


Each of the rooms have been updated with modern features, while keeping the cottage feel. Nautical touches like navy wainscoting, sisal carpet, wood headboards, brass fixtures, and woven rattan lounge chairs provide a sense of place.

Prices range from $175 to $400 per night in the peak season.


The two restaurants on site are helmed by Chef Sean Wheaton, who came to the hotel from José Andrés’ ThinkFoodGroup. Of course, the bounty of the Chesapeake is proudly featured on the menus at both Tickler’s Crab Shack and Bar Mumbo.

Tickler’s has seating indoors with views of the water, as well as a deck where you can dine right on the Bay. Classics reign supreme, with fresh seafood from the steamer, jumbo lump crab cakes, and raw bar delicacies. Drinks are simple and refreshing, from margaritas to local beers.

Bar Mumbo is modeled after a seaside tavern, with twists on familiar fare, like clams and ham, which pairs little neck clams with ham steamed in white wine and butter over house pasta. The food is complemented by classic cocktails and pitchers of frosé.

The oysters served at Wylder come from the neighboring nonprofit, Phillips Wharf Environmental Center. The educational facility also farms oysters in nearby waters and sells them to local restaurants. Oysters can filter up to 50 gallons of water per day, so increasing populations helps to reduce pollutant loads and restore the Chesapeake Bay. The oyster house is open to the public for tours.


Though you needn’t do more than relax in an Adirondack chair with a margarita watching the boats sail in, there’s plenty to entertain if you’re more of an adventurer. The hotel offers guests access to cruiser bikes, kayaks, paddle boards, and canoes. There’s also a beautiful saltwater pool for swimming and lounging, bocce ball courts, and fire pits by the shore for making s’mores or mingling with other guests. Charter fishing excursions are popular as well.

Wylder Hotel Tilghman Island: 21551 Chesapeake House Drive, Tilghman Island, Maryland 21671