The Chesapeake Bay is the largest estuary in the United States — 200 miles long, 11,684 miles of shoreline, and home to one of the greatest concentrations of waterfront bars and dock bars anywhere on the East Coast. Translation: you’re going to need more vacation days.
This is steamed blue crabs by the bushel, cold Natty Boh sweating on a screened porch over the water, and a dock bar culture so deeply baked into Chesapeake DNA that skipping it should probably be illegal. Grab a seat on the water, crack some claws, and don’t even think about leaving before sunset.
Here are some of the best beach bars on the Chesapeake Bay, Maryland to Virginia.
Seacrets Jamaica USA in Ocean City is one of the largest waterfront bars in the US — multiple bars, a lagoon, and the most festive waterfront energy in Maryland. Fager’s Island delivers sophisticated bay dining and drinking. Fish Tales, Coconuts, and M.R. Ducks complete Ocean City. On the Eastern Shore, The Crab Claw Restaurant in St. Michaels is a Maryland institution. Harris Crab House and Red Eye’s Dock Bar are the first taste of the Chesapeake for anyone crossing from Annapolis.
Annapolis is the sailing capital of America and its waterfront bar scene is the most concentrated on the Bay. Cantler’s Riverside Inn on Mill Creek has been steaming blue crabs for the Annapolis community since 1974. Pusser’s Landing and Ram’s Head Dockside serve the City Dock waterfront community. Southern Maryland’s Solomons Island — Tiki Bar and Grill Solomons and The Pier Restaurant and River Bar — delivers the quintessential Southern Maryland dock bar experience.
The Virginia side of the Bay delivers its own distinct waterfront bar culture. Waterman’s Surfside Grille in Virginia Beach is the most celebrated waterfront bar in Hampton Roads. The Northern Neck communities of Reedville, Irvington, and White Stone deliver waterfront restaurants and dock bars serving the Bay’s most scenic Virginia shoreline. From The Crab Claw in St. Michaels to Cantler’s in Annapolis — the Chesapeake bar circuit is one of the great American road trip bar crawls.
The Chesapeake is best experienced by water — a boat-based bar crawl hitting the dock bars of the Eastern Shore, Annapolis, and the Patuxent River is the definitive experience. By car, the Bay Bridge connects the Western and Eastern shores.
Blue crab season runs May through October. Order steamed blue crabs by the dozen at any dock bar and eat them properly: newspaper on the table, wooden mallet, Old Bay seasoning. Note: this is not negotiable.