Every year Deal Island, in Somerset County holds their annual Skipjack Race and Festival. This annual event showcases the last sail powered fishing fleet in the United States.

For more than 100 years, the Skipjack fleet has been an icon in the Chesapeake Bay. The white-hulled work boats have brought the prized oysters to market for decades. The Skipjacks are modelled on the lines of the classic Baltimore Skipjacks. The single-masted, wind powered workboats are the last sail powered fishing fleet in the country and remain a symbol of the Chesapeake Bay.

Island Fest, held each year over Labor Day weekend is an opportunity to see and celebrate the Skipjacks in Somerset County. The event is held over three days and includes parades, a 5k, bike races, a fair, local food and the Miss Skipjack contest. Monday begins with  the blessing of the boats at 8 am, then the highlight is the legendary Skipjack race, starting at 9:30, when once a year the boats and their crews take a day off from the oyster beds, head to Deal Island, and battle for the title of the fastest in the fleet.

For more information on the annual Skipjack races check out Deal Island’s Annual Skipjack Races and Island Fest.