Stick to Route 33, an Old Bay-dusted path full of dishes and drinks that have become synonymous with the state.
The stretch of Maryland shoreline that faces D.C. from the opposite side of the Chesapeake Bay is a special draw for seafood lovers and orange crush connoisseurs. After four months full of isolation, quarantine, and social distancing, a getaway to the Eastern Shore is a smart option for D.C.-area residents looking for a diversion that’s not swarming with summer crowds.
From Cambridge to Crisfield or Kent Island to Chestertown, there are dozens of bay towns worthy of a stop. But by sticking to a particular stretch of highway, Maryland’s Route 33, visitors will find a path practically dusted with Old Bay and full of dishes and drinks that have become synonymous with the state. That includes the crabcakes from J.M. Clayton Company in Cambridge, which claims to be the oldest working crab processing plant in the world, and Harris Creek Oysters, farmed in tributaries near St. Michaels. The signature cake from Smith Island, full of thin yellow batter and layer after layer of fudge frosting, is also a big part of Eastern Shore life.
Once they’ve crossed the Chesapeake Bay Bridge and followed U.S. 50 Route 50 down the Delmarva Peninsula, travelers can hook west onto a roughly 23-mile section of Route 33 that passes through three main towns: Easton, St. Michaels, and Tilghman Island. A one-way trip takes about two hours, which means it’s easy to plan a spontaneous visit or weekend jaunt that winds up on a peninsula jutting into the middle of the bay. If they time it correctly, day trippers can catch a waterfront sunrise and sunset on the same day, watching boats go out and come back in from the bay.
Here are a handful of stops for essential Chesapeake Bay eats along Route 33, organized by distance from the starting point in Easton.