Eat steamed crabs, stroll a boardwalk, and brake for farm-stand peaches on this four-wheeled Maryland coastal road trip.

Ocean City Boardwalk

Shop Local
Just blocks from Baltimore's Inner Harbor, the Fells Point neighborhood offers cobblestone streets and quaint shops. Browse designer dresses for work and play at Cupcake near the water ( Thirty miles down the road in Annapolis, shop totes ($54 for a backpack) made from recycled sails at Re-Sails.

Get Crackin'
Stop by the Thames Street Oyster House in Baltimore for small Chincoteague Salts oysters ($1.50 each) pulled from the Eastern Shore ( In Annapolis, get your hands messy with The Crab Feast ($26) at Jimmy Cantler's Riverside Inn.

Stretch Your Sea Legs
Pass the Naval Academy and nesting ospreys on a two-hour sail ($39 and up) aboard the Annapolis-based Woodwind. Participation is encouraged, so go on and volunteer to steer the boat.

Brake for Blackberries
After crossing the Chesapeake Bay Bridge, you'll hit farm country along U.S. 50. The family-run (since 1960) Councell Farms stand in Cordova stocks local blackberries, watermelons, and peaches.

Swing, Batter Batter
Ditch U.S. 50 in Salisbury to catch the Delmarva Shorebirds for a summer hat trick: a bag of peanuts, cold beer, and a ball game ($6 and up; After the final out, cruise to the small town of Berlin, where you can enjoy a classic Coke float ($4.25) at Rayne's Reef, a legit soda fountain shop.

Hit the Hay
After strolling the 2½-mile Ocean City boardwalk—think arcade games, saltwater taffy—rest easy at The Lighthouse Club Hotel. Each of the 23 suites has views of Isle of Wight Bay or its wetlands. Patriotic bonus: The restaurant next door serenades every sunset with the "1812 Overture." Rooms from $250;