Herring Bay

Herring Bay, named the Best Place to Sail and Best Place to Cruise, offers every service and amenity a boater could desire. Direct access to the Bay allows one to quickly hoist the sails or arrive at well-established fishing spots. Dine at local waterfront restaurants and explore countless cruising destinations.

Local Waterfront Restaurants


Dockside Restaurant
421 Deale Rd, Tracys Landing, MD 20779
American Fare & Seafood.
Open for lunch, dinner, and weekend brunch.
Visit Dockside Restaurant’s Website

Happy Harbor Restaurant
533 Deale Rd, Deale, MD 20751
American Fare & Seafood.
Open for breakfast, lunch, and dinner.
Visit Happy Harbor Restaurant’s Website

Skipper’s Pier Restaurant
6158 Drum Point Rd, Deale, MD 20751
American Fare & Seafood. 
Open for lunch and dinner. 
Visit Skipper’s Pier Restaurant’s Website

Nearby Cruising Destinations

With it’s mid-Chesapeake Bay location, countless destinations are within a day or weekend trip: