Drake's Raid Reenactment

On Saturday, May 10, 2025, Historic Florida Militia presents their annual reenactment of the 1586 raid by Sir Francis Drake's raid on old San Agustín.  

The reenactors will walk from their encampment at the Oldest House Museum Complex, and gather at 7:00 p.m. at the Governor's House before proceeding up St. George Street to Orange Street. The English and Spanish troops will engage in a battle to commemorate Drake's raid—an event that ended with Drake and his men taking and burning the town.

Participating reenactors include the Men of Menéndez and Drake's Men, member groups of Historic Florida Militia, Inc. Find information about the militia and Drake's Raid on their website.

Admission: Free

When: The reenactment of the sacking and burning of the town begins at 7:00 p.m. and concludes at 9:00 p.m.

Where: The raid reenactment begins at the Governor's House and concludes at the St. George Street Redoubt.

The Encampment: On Friday and Saturday, members of the Florida Historic Militia will hold an encampment at the Oldest House Museum. They will walk from this encampment to the Governor's House prior to the start of Drake's Raid.

History of the event: On June 6, 1586, 23 ships approached the harbor of the Spanish colonial city of San Agustín with 2,000 Englishmen under the command of Sir Francis Drake. After sighting the harbor, 1,000 of these men, led by Captain Christopher Carlile, landed on Anastasia Island the next day and mounted cannons opposite the Spanish wooden fort, which was located on what is now the Fountain of Youth Park. The cannons blazed until the Spanish forces (just 300 in number) were forced to abandon the fort during the night of June 7. On the morning of June 8, the English crossed Matanzas Bay, taking the fortification and driving the Spanish rearguard from the city.

The photo above is by D.B. Couper.