Florida Historic Militia Encampment

From 10:00 a.m. to 5:00 p.m. on Saturday, May 10, 2025, the Oldest House Museum Complex will host a re-created 16th-century-style military encampment featuring drills, weapons demonstrations, and living history interpretations. A ticket for the Oldest House Museum Complex is required to enter the encampment.

They will reenact Drake's Raid near the Orange Street redoubt in front of Ann O'Malley's on Saturday evening, May 10. The troops gather at the Governor's House and proceed up St. George Street to the Redoubt.

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: Regular park admission rates apply to visit the encampment at the Oldest House Museum Complex. 

When: The military encampment will be open from 10:00 a.m. until 5:00 p.m. at the Oldest House Museum Complex on Saturday. 

Where: The living history encampment is at the Oldest House Museum Complex, 33 St. George Street in St. Augustine. 

The reenactment of Drake's Raid is free to watch. It begins at 7:00 p.m. at the Governor's House and will conclude at 9:00 p.m. at the St. George Street Redoubt.

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.