Enjoy crabs and beer while dining on the deck or inside at Harris Crab House.

Chesapeake Bay Restaurants

By Gregory Alexander
Enjoy crabs and beer while dining on the deck or inside at Harris Crab House.

Food just tastes better when you dine on the water! Whether you are arriving via sailboat, powerboat or car, there’s something special about dining on the water. The Chesapeake Bay and its tributaries provide endless options ranging from urban dining in Baltimore’s Inner Harbor and hip and historic Annapolis  to waterside dining along the many rivers, creeks and inlets that make up the Chesapeake Bay. Here a few options to make your mouth water.

Baltimore Restaurants

Not far from Ravens StadiumNick’s Fish House has steamed crabs, a large seafood menu, and live music at its waterfront location. Speaking of crabs, try dining on the outdoor dock at the Inner Harbor at Phillips Seafood, a Maryland tradition for more than 100 years. Beyond the Inner Harbor, some popular spots in Fells Point are Barcocina for its Mexican-inspired cuisine and outdoor waterside dining, and Thames Street Oyster House, where the upstairs dining room has great views, and the à la carte raw bar offers at least 10 varieties of oysters. Little Havana near Federal Hill offers Cuban-inspired food, classic Cuban cocktails and a lively Sunday brunch. 

Annapolis Area Restaurants

In the picturesque city of Annapolis, Carrol’s Creek and Cantler’s Riverside Inn both specialize in local seafood with offerings reflecting their Chesapeake Bay heritage. Pusser’s Caribbean Grille has an exclusive dockside location on “Ego Alley” downtown and is known for its signature cocktails. The location is also ideal if you are in town in October for the United States Sailboat Show, the world’s largest and oldest in-water sailboat show. Not far away is the Chart House, located in an historic boathouse with views of Spa Creek and featuring upscale, classic Chesapeake seafood. In nearby Galesville, Pirates Cove’s casual fare includes its famous Cannon Ball Crab Cake, a perfect pairing for their great lineup of live, local musical entertainment.

Southern Maryland Restaurants

At the popular Herrington Harbour South Marina in North Beach, Mango’s On the Bay is a go-to place for boaters looking for a bite.  In Deale, oysters are the main draw at Skipper’s Pier Restaurant, and further south on Broomes Island near Hollywood, Stoney’s Seafood House offers outdoor and indoor dining, an open-air tiki bar and some of the best crab cakes around. 

Great Dining on the Eastern Shore

In Rock Hall, Waterman’s Crab House specializes in family dining, while the Osprey Point Inn is the perfect spot for a romantic dinner for two, with its lovely view of Swan Creek. In beautiful St. Michaels, The Crab Claw also has amazing views, and offers a traditional crab feast—great for families and groups wanting an authentic Maryland culinary experience. On Tilghman Island, at the Wylder Hotel's  Tickler's Crab Shack & Restaurant menus are built to highlight the freshest local products from their on-site kitchen garden and orchard to daily seafood fresh items.  On the banks of the C&D Canal in historic Chesapeake City, the Bayard House is considered to be the oldest building in town and offers picturesque views, and its menu even features an Oktoberfest selection.

Maryland crabs and corn
Enjoy crabs and beer while dining on the deck or inside at Harris Crab House.
Enjoying crabs