Living History in St. Augustine

reenactors dressed in period clothing fire guns during the reenactment of Drakes Raid

How do you make more than 450 years of St. Augustine history come to life? Ask any one of our dedicated reenactors.

Throughout the year on the streets of St. Augustine, you’ll see actors dressed in full traditional garb to commemorate historic occasions, events and battles. These living history interpreters include The Men of Menendez (1565), Drake’s Men (1586), Searle’s Buccaneers (1668) and the St. Augustine Garrison (1740). Here's where you can catch them in the act.

Historic Reenactments in Saint Augustine

1. The Living History Saunter Watch as living history interpreters present a timeline of St. Augustine’s colonial history in the town’s Historic District from the City Gates down St. George Street to Aviles Street, the oldest street in the United States.

Wearing the garb and gear of the city’s military and civilian colonial environs from 1513 to 1784, reenactors answer questions related to St. Augustine’s rich history, pose for pictures with tourists and visitors.

2. Drake’s Raid on St. Augustine took place on June 6,1586 when the Spanish settlement of St. Augustine was captured in a small fight and burned by an English expedition fleet led by Francis Drake. This was part of Francis Drake’s Great Expedition and was his last engagement on the Spanish Main before Drake headed north to the Roanoke Colony. Event scheduled in May.

3. Searle’s Sack of St. Augustine In 1668, Captain Robert Searle and his privateers sailed from Jamaica to loot the silver ingots held in the royal coffers at St. Augustine. Under the cover of night, they slipped into the harbor and attacked the sleeping town, killing 60 people and pillaging government buildings, churches and homes. The devastation wrought by these bloodthirsty pirates prompted Spain’s Council of the Indies to issue money to build a massive stone fortress on Matanzas Bay to protect the city. The Castillo de San Marcos still stands as an enduring reminder of Florida’s exciting heritage. First Saturday in March.

4. Colonial Night Watch is a two-day event held in St. Augustine the first weekend in December each year. The presentation recreates the historic Spanish night watches of colonial St. Augustine in the mid-1700s. The event begins on Friday with the Castillo by Candlelight tour where visitors come into the Castillo de San Marcos to listen to British and Spanish soldiers preparing for the siege of 1740. A full day of activities on Saturday include a flag raising in the morning, reenactments all day, and a Torch Light Parade in the evening. First Saturday in December.

5. Founder’s Day is an authentic reenactment of the day Spanish explorer Don Pedro Menendez de Aviles came ashore on September 8,1565 to claim Florida for Spain. He and his crew established the first St. Augustine settlement along the shores of what is now the Fountain of Youth Archaeological Park. The land was the home of the Native Timucua Indians and became the site where the first Mass and Thanksgiving was celebrated. Event takes place in September.


Reenactors participate in an event at Fort Mose Historic State Park in St. Augustine Fl
PicturedHIstoric Reenactment at Fort Mose

Reenactments at Fort Mose

1. Militia Muster Experience entails free musket firing demonstrations from 9-11:30 a.m. at Fort Mose Historic State Park. Youth are welcome to participate in Junior Militia training using handmade wooden toy muskets. This program is free. First Saturday of every month.

2. Flight to Freedom recreates the 17th-century experience of the hundreds of slaves who traveled in search of freedom, featuring several living history interpreters portraying the various characters who would have impacted a freedom seeker's journey to Spanish Florida. Event scheduled in February.

3. Battle of Bloody Mose is an annual reenactment of the June 26, 1740, Battle of Bloody Mose provides visitors with an exciting look at the pivotal battle between the British under the command of Georgia’s James Oglethorpe and the Spanish militia, composed of former British slaves who had been granted their freedom by the Spanish. Event scheduled in June.

Related Content: