Best Beach Bars: the Chesapeake Bay

Best Beach Bars on the Chesapeake Bay

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.

An arched metal sign reads BOARDWALK OCEAN CITY, MARYLAND with silhouettes of beach and amusement activities, including people, a surfer, Ferris wheel, and cyclist, against a clear blue sky.

Ocean City & the Maryland Eastern Shore

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.

A coiled yellow rope rests on the edge of a boat, with fishing boats and a harbor in the background. The sun is setting, casting a golden glow over the water and creating a warm, tranquil scene.

Annapolis & Southern Maryland

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.

A stack of crab traps and a wooden basket sit on a dock by calm water, with boats and a white building in the background under a blue sky.

Virginia Chesapeake Waterfront

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.

Planning Your Chesapeake Bay Bar Trip

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.

More Bars on the Bay

The Bay is 200 miles long and most of it is worth exploring. Ocean City and the barrier island bars get the summer crowds. The real Chesapeake — crabs, skipjacks, working watermen, screen doors on the restaurants — runs up both shores from the bridge all the way to Havre de Grace.

Annapolis & Baltimore
Beacon Waterfront Galley · Boatyard Bar & Grill · Davis’ Pub · The Choptank · Little Havana · Nick’s Fish House · Raw and Refined

Eastern Shore — Upper Bay
Big Owl Tiki Bar · Fisherman’s Crab Deck · The Jetty · Admirals Beachside Bar · Harbor Shack · Passages Bar & Grill · Waterman’s Crab House · Libbey’s Coastal Kitchen · Kentmorr Beach Bar · Fairlee’s · JelLEEfish Joel’s · Shanty Beach Bar

St. Michaels, Oxford & Tilghman
Foxy’s Harbor Grille · Harrison’s Harbour Lights · Capsize OXMD · Doc’s Sunset Grille · Robert Morris Inn · Bar Mumbo · Tickler’s Crab Shack

Cambridge, Deale & South Bay
Blue Point Provision Co. · Portside Seafood · Happy Harbor · Skipper’s Pier · The Boathouse at Anchored Inn · Wharf 38 · Angler’s Seafood Bar · Charles Street Brasserie · La Vela · The Island Hideaway · The Lighthouse

Pasadena, Essex & Upper Bay
Mike’s Crab House North · The Rumor Reel · Brewer’s Landing · Charly’s Waterfront · LoonAsea · McFaul’s Oyster and Reel · The Vineyard Wine Bar · Tidewater Grille · Nauti-Goose