Meet the 2025 Bridge Officers

The Eastern Shore Sailing Association was founded in 1974 with 76 charter members who shared a love of racing and cruising. Early years were marked by ambitious schedules, spirited regattas, and hallmark events like the Crab Feast, Oyster Roast, and the first Memorial Day Invitational. By the late 1970s, fleets on both the Choptank and Tangier rivers were thriving, and ESSA launched youth sailing programs, cruising traditions, and its first printed yearbook. Membership steadily grew, and the association quickly became known across the Bay for its racing and camaraderie.

Through the 1980s and 1990s, ESSA expanded to include new fleets in Ocean City and Crisfield, hosted popular regattas, and introduced sail training that inspired a new generation. While participation ebbed in the late 1990s, dedicated members rallied to rebuild, keeping the club’s racing and cruising traditions alive. The early 2000s brought renewed energy, with record participation in regattas, stronger ties between fleets, and new communications through newsletters, websites, and online race results.