Maryland’s Eastern Shore

Exploring the quaint towns along the Chesapeake Bay

As a native marylander, I’ve crossed the William Preston Lane Jr. Memorial Bridge—commonly known as the Chesapeake Bay Bridge—hundreds of times, but its majesty still amazes. The twin spans, with arching cables suspended between towers that look like giant steel rulers in the distance, curve over four miles of dark, choppy water (that’s more than twice the length of the Golden Gate Bridge). About a forty-five-minute drive from Baltimore and an hour from Washington, D.C., the bridge links Maryland’s urban, congested Western Shore to its intently rural Eastern Shore. When I was young, my family made yearly outings to Ocean City, the Eastern Shore’s sprawling resort destination along the Atlantic. These days I prefer to linger a bit more inland, meandering through the area’s small, relaxed towns and absorbing the Chesapeake’s calming beauty.

Easton, thirty miles from the Bay Bridge, makes an ideal central base for explorations. It began as a colonial community in the early 1700s, and history buffs can visit the Third Haven Meeting House, a Quaker gathering place completed in 1684 that remains in use. A wealthy populace of D.C. commuters and retirees makes Easton the Eastern Shore’s biggest haven for the arts. Galleries line the verdant streets of its small downtown, and the Academy Art Museum holds a permanent collection whose works of American artists include James A.M. Whistler and Richard Diebenkorn. My current favorite place to stay there is the Bartlett Pear Inn (rates $169 to $279 in the summer), a bed-and-breakfast with charming, colorful rooms and a fine-dining restaurant. Co-owner and chef Jordan Lloyd, an Easton native, cooked around the country—including a stint at Alpharetta’s defunct Trattoria Monaco in the mid-2000s—before opening the inn with his wife, Alice, three years ago. Lloyd skillfully incorporates local meats and vegetables (order anything with sweet corn and tomatoes) into his ever-changing menu.

If you’re in Maryland in the summer, you should of course eat at least one dinner at a crab house. At the Masthead at Pier Street Marina, a restaurant on the edge of the water in sleepy Oxford, twenty minutes from Easton, order cream of crab soup (a local tradition) and the steamed crabs served on brown butcher paper. If you’re a newbie, a server will gladly introduce you to the art of picking crabs using a paring knife and a wooden mallet. Raucous Harris Crab House, just ten minutes over the Bay Bridge, often sources the heftiest crabs; its “jumbo” or “extra-large” sizes yield the most succulent lumps of meat.

In nearby Saint Michaels, a historic port town that’s popular with tourists, you can board the Skipjack Rebecca T. Ruark, a working seafood boat, for a two-hour cruise that includes an oyster-dredging demonstration. Landlubbers may prefer a slow drive or meditative hike through the 27,000-acre Blackwater National Wildlife Refuge, absorbing the marshy, otherworldly flux between land and water while looking out for ospreys and, if you’re lucky, a bald eagle.

Photograph by Ralph Young