Fairlee’s Restaurant and 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.

Weathered wood, cold beer, and the water right there, Shanty Beach Bar feels like its always been on the Chester River because it has, and the crowd reflects exactly who the Eastern Shore actually belongs to.

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.