Annual Skipjack Festival and Race

Date, Time, Location:

Sunday, August 31st – Monday, September 1st

Ralph Abbott Road, Deal Island Historic District

Event Details:

Skipjack racing on the Chesapeake Bay dates back to as early as 1872, when watermen held “shakedown sails” to test their boats before the oyster season—often turning into friendly but competitive, and sometimes wager-based, contests. The first official Skipjack Sailing Workboat Race was held in June 1927, marking the beginning of a long-standing maritime tradition.

Deal Island was once the “home port” for a large fleet of skipjacks and continues to be home to several of the remaining vessels still used commercially for oystering on the Chesapeake Bay. Since 1959, Deal Island has hosted its annual Labor Day Weekend Skipjack Race, celebrating the legacy of these historic vessels. The race features both working and non-working skipjacks—remnants of a once-thriving fleet that operated extensively from the 1880s through the 1970s. While only a few remain today, many have been carefully restored and are still seaworthy.