For a True Taste of the Chesapeake, Look to Maryland’s Eastern Shore

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.

Mile 0: Shore Barbecue Company

137 N Harrison Street, Easton

Baltimore may have popularized the pit beef sandwich, but it’s become a statewide tradition for many barbecue joints and smokehouses, including Shore Barbecue Company in Easton. The order-out spot serves pit beef smoked for hours over a charcoal fire, then sliced in thin ribbons and placed on a kaiser roll with onions and a tiger sauce that combines horseradish and mayonnaise with a blend of herbs and spices.

Mile 3: Town and Country

28248 St. Michaels Road, Easton

A green frog on the side of the road identifies this roadside beer, wine, and liquor store. It’s a mom-and-pop shop that has a reputation for being one of the best places to buy Maryland craft beers, wines, and spirits. But it also has a deli counter with a homemade chicken salad and duck-BLT sandwich, paying homage to Maryland’s status as a capital for waterfowl and poultry. Curbside pickup is available. Call in orders to (410) 822-1433.

Mile 9: Rise Up Coffee Roasters

1216 S Talbot Street, St. Michaels

Rise Up Coffee is an independent, small-batch coffee roaster and retailer that’s grown to 10 locations over the past 15 years. The original, in St. Michaels, is a roadside shed located in a strip mall parking lot. The coffee drive-thru sells single-origin beans sourced from around the world. All the coffee is certified organic and fair trade, including a Maryland roast that’s a medium blend with subtle spice notes.

Mile 10: Inn at Perry Cabin

308 Watkins Lane, St. Michaels

A go-to for special-occasion dinners, the Inn at Perry Cabin serves Maryland rockfish, oysters, and crabs in a variety of formats, from crab imperial to crabcakes topped with caviar. There’s even a macaron seasoned with Old Bay. Try the three-course menu option, which starts with a seafood tower and finishes on a sweet note with Smith Island cake. Recently, the Inn added what has turned out to be one of the more creative options for limiting exposure to the virus: private greenhouses and gazebos. “We came up with the experience pre-COVID,” chef Gregory James says. “We wanted to provide an intimate experience right on the water that would provide exclusivity from our dining room. It just happened that the privacy and physical distancing of the houses work perfectly in our current environment.”

Mile 11: Foxy’s Harbor Grille

125 Mulberry Street, St. Michaels

This boater bar and restaurant makes a quality orange crush, a cocktail that’s claimed by Ocean City but that has gradually become known as the drink of choice for anyone eating crabs by the water. Foxy’s recently expanded to occupy more space, including a patio that’s perfect for gawking at powerboats and sailboats. Order up a few rounds of crushes and feast on a crab pretzel, loaded with crab dip and melted cheddar cheese. Adding bacon, scallions, and more cheese is optional. Online ordering is available for takeout, with indoor and outdoor seating at the restaurant.

Mile 12: Carpenter Street Saloon

113 S Talbot Street, St. Michaels

This standby on Carpenter Street, or C-Street, as it’s known by locals, is known for breakfasts full of scrapple — a Delmarva Peninsula favorite. Biscuits and gravy, “S.O.S” (aka creamed chipped beef), and home fries are also served around the clock at the pub. As the days fade, it turns into a late-night haunt for crab balls, crabcakes, and soft-shell crab sandwiches. Breakfast, lunch, and dinner are offered in either a dine-in or carryout mode.

Wolfgang Kaehler/LightRocket via Getty Images

Mile 13: The Crab Claw

304 Burns Street, St. Michaels

This quintessential seafood house and crab deck has been family-owned and -operated for six decades. Steamed crabs come piled high on trays, and there’s plenty of Old Bay seasoning to go around. Customers can also find oysters on the half shell, crab imperial, steamed cherrystone clams, and fried soft-shell crab sandwiches when they’re in season.

Mile 14: Chesapeake Landing Restaurant

23713 St. Michaels Road, St. Michaels

Locals flock to this seafood market to find the freshest selection of blue crabs, oysters, shrimp, and other regional seafood, including lobsters shipped in daily from Maine. An attached restaurant has outdoor dining, and it’s a reliable option to pick steamed crabs. For less mess, there’s also crab dip, crab pretzels, crab balls, and crab meat nachos.

Mile 22: Tilghman Island Country Store

5949 Tilghman Island Road, Tilghman

Store clerks with thick Maryland accents greet customers with a “Hello, hun” at this country store that feels trapped in time. Classic Chesapeake-style to-go options include deviled eggs topped with Old Bay and Maryland fried chicken seasoned with more crab spice. There are plenty of desserts here, including Smith Island cake and pastries such as cinnamon rolls and banana nut muffins. Amanda Cook, who was previously head pastry chef for Spike Gjerde’s A Rake’s Progress at the Line hotel in D.C., now sells her sweets on the tiny island of 854 people. She’s set to open a wholesale operation called Tilghman Island Baking Co., but for now she’s experimenting by supplying sweets to the quaint country store and other shops in town. A crush cocktail bar opens every weekend with orange, grapefruit, and orange-grapefruit cocktails. This is also one of many places to buy bottles of Lyon Rum and Gray Wolf vodka, gin, and agave-based “lobo,” all of which come from a craft distillery in St. Michaels. Call in to-go orders for weekly specials to (410) 886-2777.

Mile 23: Tickler’s Crab Shack & Restaurant at Wylder Hotel Tilghman Island

21551-A Chesapeake House Drive, Tilghman

This waterfront property boasts one of the best crab decks on the Eastern Shore. Homegrown executive chef Jordan Lloyd says cooking with regional delicacy will never get old. “I can’t seem to get enough,” he says before launching into the ingredients of a crab dip that includes crustaceans caught in the same day, cream cheese, a Chesapeake spice blend unique to Tickler’s, cream cheese, citrus, mayonnaise made with farmers’ eggs, and herbs from the resort’s garden. Cook, the former D.C. baker, also makes pretzel rolls for the resort restaurant. Lloyd is no stranger to the District, either, having worked as a chef under Michel Richard at Citronelle and Cedric Maupillier at Mintwood Place. At Tickler’s, he’s found a comfortable spot by the water.

“There is a special essence of home here, and when it comes to quality of ingredients, it is about 50 feet from my kitchen to the Choptank River,” he says.

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