The Historic Gates of St Augustine, Florida

Founded in 1565, St. Augustine is the oldest continuously occupied settlement of European and African-American origin in the United States. Forty-two years before the English colonized Jamestown and fifty-five years before the Pilgrims landed at Plymouth Rock, the Spanish established at St. Augustine this nation's first enduring settlement.

St. Augustine was intended to be a base for further colonial expansion across what is now the southeastern United States, but such efforts were hampered by apathy and hostility on the part of the Native Americans towards becoming Spanish subjects. The Saturiwa, one of the two principal chiefdoms in the area, remained openly hostile. In 1566, the Saturiwa burned St. Augustine and the settlement was relocated. Traditionally it was thought to have been moved to its present location, though some documentary evidence suggests it was first moved to a location on Anastasia Island. At any rate, it was certainly in its present location by the end of the 16th century.

Following the failure of the English Roanoke colony in Virginia, where no survivors were discovered by an overdue supply expedition, the English blamed the Spaniards of St. Augustine for its disappearance. Consequently, on June 6, 1586, English privateer Sir Francis Drake raided St. Augustine, burning it and driving surviving Spanish settlers into the wilderness. However, lacking sufficient forces or authority to establish an English settlement, Drake vacated the area.

In 1668, English privateer Robert Searle attacked and plundered St. Augustine. In the aftermath of his raid, the Spanish began in 1672 to construct a more secure fortification, the Castillo de San Marcos. It stands today as the oldest fort in the United States. Its construction took a quarter of a century, with many later additions and modifications.

King Charles II of Spain proclaimed in 1693 that runaway slaves from British lands would be given their freedom in Florida provided they converted to Catholicism. Forty-five years later, Florida’s governor approved a settlement for ex-slaves just to the north of St. Augustine. Called Fort Mose, it was the first legally sanctioned free black town in North America. The fort, originally known as Gracia Real de Santa Teresa de Mose, was established in 1738 as part of the outer defenses of St. Augustine. During the many British colonial attacks on St. Augustine, Blacks generally stood side-by-side with Native Americans and white Spaniards in defending the city.

In 1700,Spain’s King Charles II died without an heir. Soon, most of Europe was embroiled in a conflict with each country supporting its own Protestant or Catholic candidate for the Throne. This War of Spanish Succession boiled over into the New World where it became known as Queen Anne’s War. This was the excuse South Carolina's Governor James Moore needed. In 1702 he led an expedition against St. Augustine and its new fort. After 58 days, the British retreated, but as they left, they burned St. Augustine to the ground.

In 1704, St. Augustine was spurred into action to better defend the city after numerous British attacks. The Spanish decided to fortify their outer rims and began to construct the Cubo Line. Palmetto logs were layered and stretched across northern St. Augustine, backing a large, earthen wall, fortified with a moat, a cannon and a wooden gate towards the road that we now know as San Marco Avenue. Bayonets and cactus were planted atop the structure to add height. Soon, the Rosario Line was built and ran south, encircling the city. With this fortification, the “Ancient City” was impenetrable.

Moving southward on the coast from the northern colonies, the British founded Charleston in 1670 and Savannah in 1733. The War of Jenkins' Ear gave Governor Oglethorpe an excuse to have British forces attack St. Augustine from their colonies in the Carolinas and Georgia. On June 13, 1740, Oglethorpe began the siege of St. Augustine by blockading the city including the Matanzas Inlet. Oglethorpe placed troops and cannon batteries on Anastasia Island to fire on the city and the Castillo. He hoped that a sustained bombardment and blockade of St. Augustine would cause Governor Montiano to surrender the city and fortress to the British. The English guns fired on the Castillo, but were unable to breech the walls which were at the farthest extent of the British cannon range. Fearing the approaching hurricane season, the British fleet decided to sail north for safer waters. Lacking naval support, Oglethorpe raised the siege on July 20, 1740.

Alone among the colonies in the present-day United States, both West and East Florida remained loyal to the British crown during the American Revolution. Thousands of British loyalists fled the American Thirteen Colonies during the course of the war and settled in St. Augustine which served as a safe haven for Tories.

Britain reigned supreme in North America in 1763, having wrested away Canada from the French and Florida from the Spanish in the Seven Years’ War. During their 21 year tenure, the British divided the colony into East Florida, with its capital in St. Augustine, and West Florida, with its capital in Pensacola. They didn’t have time to seriously develop St. Augustine into a British colony because they were forced to return Florida to Spain in 1784 as part of the same treaty that granted the American colonies their independence.

The James Madison administration secretly authorized a paramilitary invasion of Spanish Florida in the hope of annexing the territory. The incursion took place in 1812, when a band of United States militiamen arrived as part of an ill-conceived and internationally unlawful bid to annex East Florida to the United States. The Madison administration vehemently denied any responsibility or support for these military actions and the militia withdrew.

St. Augustine incorporated the Old City Gates into the Cubo Line in 1808. The imposing pillars sit at the start of St. George Street, towering above travelers at three-stories high. These blocks were supplemented with coquina, a soft limestone made from broken shells. They replaced an earlier entryway made of wood, adding strength to the fortification. Royal engineer Manuel de Rita built these coquina pillars and it was the Cubo Line’s last reconstruction.

Because the earthworks and timber deteriorated over time, the walls were rebuilt and repaired over the more than 100 years that they protected the city. Major construction projects took place during the 1730s and again in 1808. The last known time the walls were used in conflict was during the Second Seminole War (1835-1842). War parties of Seminoles struck around St. Augustine, but advanced no closer to the city itself than the Cubo Line.

In 1819, after years of negotiations, Secretary of State John Quincy Adams achieved a diplomatic coup with the signing of the Florida Purchase Treaty, which officially completed the acquisition of Florida to the United States. Formal occupation began in 1821. Florida was organized as a U.S. territory in 1822 and was admitted into the Union as a state in 1845.

The Old City Gates were at one time the only entrance into St. Augustine. Visiting the oldest city in the United States would not be complete without taking a moment to see the Old City Gates.