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The Five-Point Weekend Escape Plan

Island Hop Around Maryland's Eastern Shore

Navigate the marshy Chesapeake coastline to enjoy peak-season crab and oyster while exploring the area’s nautical traditions.


1. Where to Stay

The Inn at Perry Cabin's rooms feature clean décor and nautical touches.  

Gaze at sailboats cruising the harbor from inside the Inn at Perry Cabin (from $390). Its 78 rooms are outfitted with touches like wide, striped couches, brass desk-lamps, and old-fashioned standing mirrors, but request room 36 for a bit of history—it was once the master bedroom of a War of 1812 veteran, who had it built to resemble a ship’s cabin.

Step into a scene from Gone With the Wind at the Brampton Inn (from $179), a 19th-century plantation house near Chesterton. Seven rooms in the old mansion and six separate cottages all feature southern touches like flower prints and four-poster beds, while the Fairy Hill duplex suite offers a wood-burning fireplace in the sitting room and a whirlpool tub. In the evening, relax at the brandy honor bar in the little library on the first floor.

Pad around the original thick-planked wooden floors of the Kent Manor Inn (from $149), built in 1820. Of the 24 guest rooms, request one on the second floor for more space, ten- to twelve-foot ceilings, and wide balconies. Borrow one of the in-house bikes and pedal around the property—a 220-acre farm—or out to the six-mile Cross Island trail that loops through tranquil Terrapin Beach Park.

Published on Oct 6, 2011 as a web exclusive.

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