St Augustine FL: America’s Oldest City

Forty-two years before the English established their colony at Jamestown, Virginia, forty-three years before the Spanish settlement at Sante Fe, New Mexico, and fifty-five years before the Pilgrims landed at Plymouth Rock, Massachusetts, a group of Spanish settlers established a colony at St Augustine, on the east coast of the Florida peninsula. Today, at 450 years old, “St Augie” is the oldest existing city in the United States


Castillo de San Marcos, St Augustine, FL

On March 3, 1513, Juan Ponce de Leon left the Puerto Rican port of Punta Aguada with three ships and sailed north. De Leon had traveled from Spain to the New World on Columbus’s second voyage in 1493, becoming a Provincial Governor on the island of Hispaniola and then Governor of Puerto Rico. According to legend, de Leon’s latest voyage was in search of the fabled island of Bimini, where the Fountain of Youth was said to be located. In reality, de Leon was searching for the same things every Spanish Conquistador searched for–land and gold.

On April 2, during the Easter Week Festival of Flowers, de Leon sighted land and, thinking he had found another Caribbean island, he named it La Florida (“the flowered land”) in honor of the holiday. He had, unknowingly, landed on the shore of an entirely new continent–in what is now Florida, likely someplace near present-day Cape Canaveral. (De Leon found that he was not the first European to reach Florida, though: one of the Timucua natives that he met onshore spoke a few words of Spanish, likely taught to him by a shipwrecked sailor or pirate.) After sailing for Spain and receiving a royal appointment as Governor of Florida, de Leon returned in 1521, was wounded by an arrow in a fight with the Florida natives, and sailed to Cuba where he died.

It wasn’t until almost forty years later that any serious attempt was made by the Spanish to settle a colony in Florida. In 1559, Tristán de Luna y Arellano founded a small Spanish town near what is now Pensacola, but within two years the colony had been hit by hurricanes, attacked by local natives, and suffered famine brought about by crop failures, and was abandoned. By this time the French had also found Florida, and in 1562 the French Huguenot Jean Ribault landed at the St Johns River before sailing further north and starting an unsuccessful colony called Charlesfort, on what is now Parris Island, South Carolina. In 1564, another French Huguenot who had sailed with Ribault, named René Goulaine de Laudonnière, landed at the “River of Dolphins”, now the Matanzas River, and built a palisaded stronghold called Fort Caroline. A short while later, French deserters from Fort Caroline had turned pirate and were attacking Spanish shipping, and the Spanish King sent Pedro Menéndez de Avilés to establish a Spanish base in the area and expel the French. Avilés landed at a nearby native Timucuan village on August 28, 1565, with about 800 troops and colonists, and obtained permission from the local chief to build a wooden fort next to the village. Since it was the feast Day of St Augustine of Hippo, the new Spanish settlement was named St Augustine.

At about the same time, the French explorer Ribault had returned to Fort Caroline with more troops and claimed Florida for France. When he heard about the Spanish fort being built nearby, he put five hundred troops on a small fleet and sailed towards St Augustine, intending to destroy it. The fleet was hit by a hurricane, however, and Ribault and about 350 survivors were stranded on what is now Anastasia Island. At St Augustine, meanwhile, during the same hurricane, Menéndez de Avilés was already marching his own army overland to Fort Caroline, attacking it at dawn after the hurricane ended, and overpowering the Fort. After massacring everyone inside, Menéndez de Avilés then went south and found Ribault and his stranded men, and killed them too. Fort Caroline was renamed Fort San Mateo, and a Spanish garrison was left there.

But Florida was not yet firmly in Spanish hands. In 1566, one of the local native bands attacked St Augustine and burned it, forcing the Spanish to rebuild a few miles away. Two years later, a group of French troops under Dominique de Gourgues, accompanied by several bands of natives, attacked Fort San Mateo, burning it and killing all its occupants, and launched several raids on the town of St Augustine. In June 1586, the English privateer Sir Francis Drake also landed troops and attacked the town, burning it before leaving. At around the same time, the administration of St Augustine was taken over by the Spanish King as a royal colony, and a few additional settlers began arriving from Spain. But isolated and alone in the New World, the Florida colony remained a backwater, and St Augustine remained more as a military outpost than as an actual colony.

In 1670, the British established their own colony at nearby Charleston, South Carolina, and took a new interest in Florida. As a result, in 1672 the Spanish at St Augustine constructed a new stone fort, Castillo de San Marcos, to defend the town. Tensions grew as the English continued to build more plantation colonies in the Carolinas: the Spanish were a haven for escaped plantation slaves who, as long as they converted to Catholicism, were welcomed in Florida as free men. One group of former slaves founded the town of Gracia Real de Santa Teresa de Mose, just north of St Augustine–the first free African-American town in the US. Fort Mose was constructed there shortly later.

Twice, in 1702 and in 1740, the British launched an invasion of Florida from their colonies in Georgia, and unsuccessfully laid siege to Fort Mose and St Augustine. In response, the Spanish built a third fortress, Fort Matanzas, to protect the city.

By 1756, Spain and England were themselves at war. The British won, and as part of the 1763 peace treaty, Florida was turned over to British rule. The English government split the colony into two halves: East Florida, with its capitol in St Augustine, and West Florida, with Pensacola as its capitol. The British ruled Florida for the next 21 years.

During the Revolutionary War, the Castillo de San Marcos was converted into a prison for captured American rebels (three signers of the Declaration of Independence were imprisoned there). The Spanish King, meanwhile, gave financial and military aid to the American colonists, and when the United States won its independence from Britain in 1783, part of the peace treaty returned Florida back to Spain. But as the Spanish Empire began to decline in power during the late 18th and early 19th century, the fledgling United States began to exercise more influence in Florida, and illegal settlements and armed incursions became more frequent. In March 1812, the US sent gunboats and troops to lay siege to St Augustine in an attempt to conquer the colony, but they were forced to withdraw when the War of 1812 broke out with England. In 1817, American troops under General Andrew Jackson once again invaded Florida in the First Seminole War, and gained control over much of the peninsula. In 1821, Spain began to view the isolated colony as no longer important, and formally sold the provinces of East and West Florida to the United States for $5 million. They were incorporated into the US as the State of Florida in 1845.

The Castillo de San Marcos, now renamed Fort Marion, became an important military base in the Second Seminole War in 1835. During that war the Seminole chief Osceola was invited to a peace negotiation at St Augustine, but was taken prisoner instead.

When the Civil War broke out in 1861, Florida joined the Confederacy, and a group of 25 militiamen seized Fort Marion. But the Union Navy targeted the port at St Augustine as part of its “Anaconda Strategy” to strangle the South with a blockade. In March 1862, the US warshipWabash landed at St Augustine and disembarked a group of Federal troops, who occupied the town without firing a shot. St Augustine remained in Union hands for the rest of the war.

In the 1870’s, Fort Marion was used as a military prison. A number of captives from the “Indian Wars” were held there at various times. In 1898, the fort was used as a prison camp for military deserters and disciplinary cases during the Spanish-American War.

In 1920, the fort was decommissioned, and in 1933 it was transferred to the National Park Service. Today it is designated the Castillo de San Marcos National Monument.


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