Year after year, Drake’s Raid is the most popular event in the St. Augustine History Festival. This year there were three combative forces: the Spanish, the English, and the rain. But even the rain couldn’t hold off the English for yet another victory. For a full description of this Special Event, continue scrolling after viewing the fun pictures below. Stay tuned for what 2026 will bring!

Beginning at 7:00 p.m., the armies of Spain and England will fight for possession of St. Augustine in this reenactment of Sir Francis Drake’s raid in 1586. This is an historic district-wide event, beginning at the Governor’s House on the Plaza, then continuing north to the Santa Domingo redoubt by the City Gates.

The English have won this battle every year for 439 years, but maybe this is Spain’s year?

Come Find Out!