Skipjack Races: A Triple Crown on the Chesapeake

Skipjack history comes to life on the water

There’s something very special about a traditional Chesapeake skipjack. Once a flourishing fleet, fewer than two dozen of these legendary vessels still sail today. This September, you have three opportunities to view them under full sail in a series of heritage races dedicated to preserving their legacy.

Skipjacks sailing on the Chesapeake Bay
You will have three opportunities in September to view Skipjack racing. Photo by Walter Cooper

Deal Island Skipjack Race and Festival, September 6-7. Hosted annually on Labor Day weekend since 1959, the Deal Island Skipjack Race features both working and non-working skipjacks. The two-day event begins on Sunday with live music, educational exhibits, and other vendors. Monday’s events open with a blessing of the fleet, followed by a parade of sail. Racing will begin at 9:30 a.m., in Tangier Sound. The best viewing sites are the Deal Island Harbor and along the shoreline of Tangier Sound. Learn more at skipjackheritage.com.

Skipjack Heritage Days, September 12-13. The Skipjack Heritage Days Race, held off Sandy Point just north of Annapolis and the Bay Bridge, will run alongside the Maryland Seafood Festival. Families are invited to explore the stories of the Bay through hands-on activities, educational exhibits, public skipjack sails, and Sunday’s race, viewable from the park’s East Beach festival grounds. Learn more at abceventsinc.com/maryland-seafood-festival

Choptank Heritage Skipjack Race, September 26. Sponsored by the Dorchester Skipjack Committee, the 30th annual Choptank Heritage Skipjack Race will unfold at Long Wharf in Cambridge, MD. Over the past 30 years, the sponsoring committee has raised and donated more than $200,000 to help preserve the remaining fleet of skipjacks. Each participating vessel will receive approximately $1500 in show-up money. Immediately preceding the race on the Choptank River, a parade of boats will head out of Cambridge Creek at 10 a.m. Best viewing will be from Long Wharf Park. Learn more at skipjack-nathan.org.