An iconic destination on Tilghman Island has reinvented itself—and not for the first time. Harrison’s Chesapeake House began life more than 100 years ago as a boarding house for watermen who mined the bay for Maryland’s famous blue crabs. It evolved over time into a venerated seafood restaurant and hotel, luring such political luminaries as Barry Goldwater and then-Governor George W. Bush—who sailed there on the skipjack Minnie V—as well as baseball players Stan Musial and Brooks Robinson.

Reimagined once again—this time under the Wylder Hotels brand—the property reopened after a renovation in April 2018 as Wylder Hotel Tilghman Island, a resort nestled on nine lush, waterfront acres. While the original exterior remains intact, the interiors, by Brooklyn-based hospitality design firm Studio Tack, channel “a white-washed, classic seaside resort feel that honors the architecture,” says Wylder founder and CEO John Flannigan. Guest rooms boast navy wainscoting, brass fixtures and sisal carpet, while public spaces are airy, with striped-cotton rugs and rattan furniture.

The property’s two eateries are spearheaded by chef Sean Wheaton, a seven-year alumnus of José Andrés’ Think Food Group. Tickler’s Crab Shack & Restaurant serves classic Eastern Shore fare—peel-and-eat shrimp, steamed crabs and rockfish—both inside and on an outdoor deck overlooking Harris Creek. Bar Mumbo, an upscale tavern, currently proffers snacks such as oyster shooters, crab cake and flat-iron steak entrées and local beers; during the winter, however, both restaurants will share the Tickler’s Crab Shack menu.

The resort offers 54 rooms and 10 private bungalows with shared porches; amenities include a salt-water swimming pool, 25 boat slips, a bocce-ball court and bikes for navigating the three-mile island—plus kayaks, paddle boards and canoes. Charter sailing and fishing expeditions are available.

Rates start at $158 per night for a room and $180 for a bungalow. For information, visit wylderhoteltilghmanisland.com.