Maryland's Skipjack Triple Crown of Racing

Date, Time, Location:

September 7, 8:00am | Deal Island

September 13, 11:00am | Sandy Point State Park

September 26, 10:00am | Cambridge

Event Details:

Skipjack racing returns to Heritage Days after 35-year hiatus

Skipjack racing on the Chesapeake Bay goes 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.

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.