Shanty Beach Bar

JelLEEfish Joel’s gives Chestertown’s Chester River waterfront a sandy-toes, tropical twist that the town’s formal colonial architecture doesn’t usually advertise.

On the Chester River in one of the Eastern Shore’s best-preserved colonial towns, Fairlee’s pairs consistent local seafood with cold drinks worth the detour past Kent Narrows.

Passages serves the sailing community that calls Rock Hall home port with cold beer, crabs, and the kind of reliable harbor warmth that keeps cruisers coming back at the end of every passage across the Bay.

Right on the Rock Hall waterfront, Harbor Shack does the full dock bar routine: steamed crabs, weekend live music, and working crab boats and the skipjack Elsworth as your neighbors.

Rock Hall’s most celebrated crab house, Waterman’s serves some of the Bay’s biggest, meatiest blue crabs on the old-school banquet-table format: newspapers, mallets, and a bucket, with a dock bar for boaters pulling into the harbor.