Exploring the Eastern Shore

Maryland's Chesapeake Bay offers quaint and memorable small towns, fresh-from-the-sea crab, and lots of laid-back leisure.

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Young crabbers check their nets on a dock in the St. Michaels harbor.
Photo by: David Hillegas

St. Michaels

The most popular town on the Eastern Shore, St. Michaels has a beautiful harbor with several waterfront dining options, the Chesapeake Bay Maritime Museum, and Talbot Street, studded with more restaurants and boutiques, and a classic ice-cream shop.

Where to stay: The Inn at Perry Cabin, 308 Watkins Ln.; 866/278-9601 or perrycabin.com. Five Gables Inn & Spa, 209 N. Talbot St.; 410/745-0100 or fivegables.com.

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