Port · Spanish Florida

St Augustine, Spanish Florida

St Augustine, founded by Spain in 1565, was the small capital of Spanish Florida, guarded by the coquina stone Castillo de San Marcos and kept alive by ships from Havana and silver from Mexico. Around 1715 it was also a goal for people escaping slavery in Carolina, whom Spain had promised freedom in 1693, a promise its governors did not always keep. In 1738 some of them, led by Francisco Menéndez, founded Fort Mose, the first legally sanctioned free Black settlement in what is now the United States.

Is St Augustine the oldest city in the US?

Pedro Menéndez de Avilés founded St Augustine for Spain in 1565. The National Park Service describes it as one of “the oldest continuously occupied European and African American settlements in the United States.” In plain words, it is the oldest city founded by Europeans in the mainland United States that people have lived in without a break ever since.

It is not the oldest European town in North America. Spanish towns in Mexico and the Caribbean, such as Havana, are older.

What was St Augustine like around 1715?

St Augustine was a small garrison town, a place that existed mainly to house soldiers and guard Spain’s claim to Florida. No census survives for the game’s years, but about 1,500 people sheltered in its fort in 1702 and almost 2,000 in 1740, so the town was probably somewhere in between, with Native villages nearby. The garrison numbered about 350 men before 1740.

Much of the town was new. English attackers burned it in 1702, and its oldest surviving colonial buildings date from 1703 onward.

Florida could not pay for itself. The garrison depended on the situado, a yearly payment of silver that the viceroy of New Spain, in Mexico City, was meant to send. It often came late or not at all; by 1668 more than 400,000 pesos were owed. Skilled workers, guns and rescue ships came from Havana.

When was the Castillo de San Marcos built?

Two events pushed Spain to build in stone: a pirate raid on the town in 1668, and the English founding of Charles Town in 1670, only two days’ sail to the north. Ground was broken on 2 October 1672, and the first phase was finished in 1695 at a cost of 138,375 pesos.

The fort is made of coquina, a soft rock formed from tiny shells, quarried on Anastasia Island across the bay. Its walls are about 12 feet thick, and 19 feet on the side facing the sea. Native labourers quarried the stone and gathered shell to burn for lime, and disease killed many of them. Masons and lime-burners came from Havana.

The National Park Service calls the Castillo the oldest masonry fort in the continental United States. Coquina proved a lucky choice: the soft stone squeezed together and absorbed cannonballs instead of shattering.

What happened in the siege of St Augustine in 1702?

Governor James Moore of Carolina, a planter and slave dealer, attacked with about 800 English and Native fighters, most of the Native fighters were Yamasee allies of Carolina. His fleet appeared on 8 November 1702. Within two days nearly 1,500 people had crowded into the Castillo.

The English held the town for nearly two months but could not break the fort’s walls. On 26 December four Spanish warships arrived from Havana and Moore gave up. As his troops left they burned what remained of the town. The Spanish put the damage at 20,000 pesos or more.

Why did people escaping slavery go to St Augustine?

In 1687 a small boat reached St Augustine from Carolina carrying eight men, two women and a nursing child who had escaped slavery. They are the first recorded group of freedom-seekers in Spanish Florida, and Spain refused to send them back.

In 1693 King Charles II of Spain issued a royal decree, or cédula, promising freedom to people who escaped from the English colonies and became Catholic. As word spread, more came south, overland and by boat. Historian Jane Landers has compared this route to an early underground railroad, one that ran south.

The promise was real, but it was not always kept. Spanish governors sometimes held or sold new arrivals as slaves. Spain’s motives were also practical: every person who escaped weakened Carolina and could become a soldier for Florida, which itself still allowed slavery.

After the Yamasee War against Carolina began in 1715, many Yamasee moved south and settled near St Augustine, becoming allies of Spain. Some enslaved Africans used the chaos of that war to escape south.

Who was Francisco Menéndez?

Francisco Menéndez was a Mandinga man from the Gambia region of West Africa, born about 1700 and enslaved in Carolina. He escaped during the Yamasee War and reached Spanish Florida with his wife, Ana María de Escobar.

Instead of freedom, they were sold. According to Landers’s research, a Yamasee man first held the group as hostages, the acting governor bought them, and in 1718 Menéndez was sold to the royal accountant Francisco Menéndez Márquez, whose name he took at baptism.

Still enslaved, he became captain of St Augustine’s Black militia in 1726, and the militia helped defend the town against a raid from Carolina led by Colonel John Palmer in 1728. Menéndez learned to write and sent petition after petition asking freedom for himself and about 30 others.

What was Fort Mose?

In 1738, more than twenty years after the game begins, Governor Manuel de Montiano freed Menéndez and his companions without conditions and founded Gracia Real de Santa Teresa de Mose, about 2 miles north of St Augustine. About 38 men and their families, roughly 100 people, lived there behind earthen walls in thatched houses, with Menéndez as their captain and leader. The National Park Service calls it North America’s first free, legally sanctioned Black community.

In 1740 a British force led by James Oglethorpe captured Mose. Menéndez’s militia helped take it back, but the fort was wrecked, while the Castillo held out through a 27-day bombardment. That same year Montiano ordered Fort Matanzas built to guard the southern inlet. In 1741 Menéndez was captured at sea while sailing as a privateer, a licensed raider, and sold into slavery in the Bahamas; he was free and back in Florida by 1759.

Mose was rebuilt in 1752. When Spain handed Florida to Britain in 1763, its people sailed to Cuba with the rest of the town. The exact site of the first 1738 fort has never been confirmed; it probably lies under the marsh.

Legend or fact?

Legend says: St Augustine is the oldest European town in North America.

Records show: It is the oldest continuously occupied European-founded settlement in the mainland United States. Older Spanish towns exist in Mexico and the Caribbean.

Legend says: Anyone who reached Spanish Florida was free at once.

Records show: The 1693 decree promised freedom, but governors broke it. Menéndez and others were sold as slaves until their petitions and Montiano’s order of 1738 freed them.

Legend says: Spain freed them simply out of kindness.

Records show: It was also strategy. Freedom-seekers weakened Carolina and gave Spain soldiers and a defensive buffer north of town, and slavery remained legal in Florida.

Legend says: Fort Mose was the first free Black town in America, full stop.

Records show: It was the first legally sanctioned one in what is now the United States. Earlier communities of people who freed themselves existed, so the qualifier matters.

Legend says: Fort Mose was a stone fort like the Castillo.

Records show: It had earthen walls and thatched houses.

Sources

  1. Fort Mose, National Park Service, Fort Matanzas National Monument. Montiano’s 1738 grant, about 38 men and 100 people, earthen walls and thatched huts, its status as the first free legally sanctioned Black community, 1740, rebuilding in 1752 and the move to Cuba in 1763.
  2. Francisco Menéndez, Jane G. Landers, adapted by J. Almeida and S. J. Niven (Hutchins Center, Harvard), via Enslaved.org. Menéndez’s birth in the Gambia region about 1700, escape during the Yamasee War with his wife, sale in 1718, militia captaincy in 1726, petitions for about 30 others, freedom in 1738, capture in 1741, return by 1759 and the move to Cuba.
  3. Freedom Fort, Daniel Weiss, Archaeology magazine (Archaeological Institute of America) (2024). The 1687 arrivals, the 1693 decree, Menéndez held as a hostage and then sold, his captaincy, Montiano’s 1738 order, and Landers’s underground railroad comparison.
  4. What Was America’s First Black Town?, Henry Louis Gates Jr., PBS, The African Americans: Many Rivers to Cross (2013). Spain’s policy of freedom from 1687, Menéndez as a Mandinga man (the source for his Mandinga identity), his militia leadership and the founding of Mose.
  5. The little-known story of the enslaved Africans who found freedom in the European fight over North America, Smithsonian Magazine. The 1687 group of eight men, two women and a nursing child; that the original 1738 site has not been found.
  6. Black Society in Spanish Florida, Jane Landers (University of Illinois Press) (1999). The standard scholarly history of the 1693 decree, the freedom-seekers and Mose.
  7. Founding of Castillo de San Marcos, National Park Service, Castillo de San Marcos National Monument. The 1668 raid and Charles Town as motives, ground broken in 1672, the situado from New Spain and its arrears, masons from Havana and Native labourers.
  8. Coquina: The Rock that Saved St. Augustine, National Park Service, Castillo de San Marcos National Monument. Coquina, wall thickness, completion of the first phase in 1695, and how the stone absorbed cannon fire in 1702 and 1740.
  9. Castillo de San Marcos (education guide), National Park Service, Fort Matanzas National Monument. Building dates and cost of 138,375 pesos, coquina from Anastasia Island, and the 27-day bombardment of 1740.
  10. The Siege of 1702, National Park Service, Castillo de San Marcos National Monument. James Moore’s attack, about 1,500 people in the fort, the relief from Havana on 26 December and the burning of the town.
  11. Castillo de San Marcos (NPS Interpretive Series), National Park Service (traditionally credited to Albert Manucy), via npshistory.com. About 800 attackers in 1702 and 20,000 pesos of damage, the 1728 Palmer raid, a garrison of about 350 and almost 2,000 people sheltered in 1740.
  12. St. Augustine Town Plan Historic District, National Park Service, National Register of Historic Places. Founding in 1565 by Pedro Menéndez de Avilés, the “oldest continuously occupied” wording, and colonial buildings dating from 1703 onward.
  13. Castillo de San Marcos National Monument, National Park Service. The Castillo as the oldest masonry fortification in the continental United States.
  14. Fort Matanzas: history and culture, National Park Service, Fort Matanzas National Monument. Fort Matanzas ordered by Montiano in 1740 to guard the southern inlet.
  15. Yamasee War, Wikipedia (citing William L. Ramsey, The Yamasee War, 2008, and other histories). Additional source: the war’s start in 1715 and many Yamasee moving near St Augustine (not the escape of enslaved Africans during the war, which rests on Landers).

Written for Silver & Sails. Facts last checked against these sources on 11 October 2026. Found a mistake? Tell us.