A new race brings historic Skipjack sailboats to the Western Shore
A new Chesapeake Bay tradition will set sail this fall when Skipjack Heritage Days debuts at Sandy Point State Park near Annapolis. The event, to be held September 13-14, will celebrate the legacy of America’s last working sailing fleet with a two-day festival of culture, community, and coastal heritage.

Running alongside the Maryland Seafood Festival, Skipjack Heritage Days invites families to explore the stories of the Bay through hands-on activities, educational exhibits, public skipjack sails, and a Sunday skipjack race viewable from shore.
Step aboard a piece of history
“Skipjacks are living history,” says Susan Schneider, organizer with Skipjack Heritage, Inc. “They’re iconic to our region, and this festival offers a rare chance to experience them up close.”
Event highlights will include a parade of skipjacks at 11 a.m. on Sunday, September 14, followed by a race at noon, which will be organized in conjunction with Eastport Yacht Club. The course will take boats from Sandy Point Light to Baltimore Light and back.
The festival will also feature public boat rides aboard skipjacks, a Champions of the Chesapeake family area led by Living Classrooms and Annapolis Maritime Museum, presentations on African American watermen by Blacks of the Chesapeake, and a gathering of more than a dozen skipjacks and buy boats.

In 1985 the skipjack was named the Maryland State Boat. Once numbering 1400 vessels, the skipjack fleet now has fewer than 20 boats in working condition. This festival honors these vessels and the generations of watermen—especially Black watermen—whose stories shaped the Chesapeake Bay.
A triple crown series
Skipjack Heritage Days will be the first gathering of such boats in Annapolis since the 1960s. The new race will join two long-running Eastern Shore races—the Deal Island Skipjack Race and Festival August 31 to September 1, and the Choptank Heritage Skipjack Race Saturday, September 27. The new Annapolis event will create a triple-crown-type series over a four-week period.
The Maryland Seafood Festival runs Saturday, September 13 and Sunday, September 14 from 11 a.m. to 7 p.m. The skipjack race will begin at noon on Sunday. Admission to the Maryland Seafood Festival includes full access to all Skipjack Heritage Days activities. Tickets may be purchased at abceventsinc.com/maryland-seafood-festival.
The event seeks to preserve the stories of working watermen and Black maritime heritage, engage and educate families about Bay ecology and history, revive skipjack racing traditions and foster pride in local culture, and promote tourism, economic development, and environmental awareness. Volunteers, sponsors, and supporters are invited to help make this celebration a success. Learn more and find out how to get involved at The Last Skipjacks Project.