St. Augustine, Florida – Oldest U.S. City


Located in Northeast Florida, St. Augustine is the oldest continuously occupied European-established settlement and port in the continental United States. The area was first explored by Spanish Puerto Rico Governor, Juan Ponce de Leon on April 3, 1513, when he landed, remained for five days, and claimed the region for the Spanish Crown.

The Alcazar Hotel is now the Lightner Museum in St. Augustine, Florida

The Alcazar Hotel is now the Lightner Museum in St. Augustine, Florida. Photo by Detroit Photographic Co., 1902

However, it would be more than 50 years before any settlement would be established. Though other attempts at European colonization were made in Florida by the Spanish and the French, all failed until Spanish Captain Pedro Menendez de Aviles arrived on September 8, 1565. Sailing through the St. Augustine Inlet into Matanzas Bay he, along with 1,500 soldiers and colonists disembarked near the Timucuan Indian town of Seloy. He also brought the first slaves in what would become the United States. Taking possession of the territory along the river, he founded a settlement, naming it St. Augustine because he first sighted Florida on August 28, St. Augustine’s Day, a Catholic holiday.

Menendez’s goal was to dig a quick fortification to protect his people and supplies as they were unloaded from the ships, and then to take a more proper survey of the area to determine the best location for the fort.

Pedro Menendez de Aviles, by Francisco de Paula Marti, 1791

Pedro Menendez de Aviles, by Francisco de Paula Marti, 1791

In the meantime, Frenchman, Jean Ribault had also sailed to America to re-supply the French post of Fort Caroline, in today’s South Carolina. Learning of Menendez’s arrival in Florida, he and his men sailed on September 10th to attack and wipe out the Spanish at St. Augustine, but a hurricane carried his ships far to the south, wrecking them on the Florida coast between present-day Daytona Beach and Cape Canaveral.

At the same time, Menendez led a force to attack Fort Caroline. Since most of the soldiers were absent, Menendez was easily able to capture the French settlement, killing most of the men in the battle. Some of the inhabitants, including Rene de Laudonniére, who had founded Fort Caroline, and the artist Jacques LeMoyne, were able to escape to ships and return to France. Menendez spared the women and children and sent them by ship to Havana.

However, Menendez then learned from Timucuan Indians that a group of white men were on the beach a few miles south of St. Augustine. He marched with 70 soldiers to where an inlet had blocked 127 of the shipwrecked Frenchmen trying to get back to Fort Caroline. With a captured Frenchman as a translator, Menendez described how Fort Caroline had been captured and urged the French to surrender. Despite rumors to the contrary, he made no promises to spare them. Having lost most of their food and weapons in the shipwreck, the French surrendered. However, when Menendez then demanded that they give up their Protestant faith and accept Catholicism, they refused. In the end,111 Frenchmen were killed. Only 16 were spared – a few who professed to be Catholic, some impressed Breton sailors, and four artisans needed at St. Augustine.

Two weeks later, the sequence of events was repeated. More French survivors appeared at the inlet, including Jean Ribault. On October 12th, Ribault and his men surrendered and met their fate, again refusing to give up their faith. This time 134 were killed. From that time, the inlet was called Matanzas — meaning “slaughters” in Spanish.

St. Augustine became the capital of Florida and the Spanish military headquarters of North America. Its governors manned forts and policed the coast from Virginia to Florida for the next four decades, repulsing efforts of other nations to establish colonies in the territory. One of the most formidable attacks on St. Augustine was made in 1586 by British Admiral Sir Francis Drake, who sacked and burned the town. The Spanish colonists fled to forest refuges during the raid, but, later returned and rebuilt their homes.

Castillo de San Marcos Plaza

Castillo San Marcos Courtyard, photo by Kathy Alexander, 2017.

St. Augustine was safer after it became the headquarters of missionary activities among the southeastern Indians, and through its 40 or more mission towns, controlled the natives and defended the frontier against the French and English. However, it was still an attractive target for aggressors. In 1668, English privateer Robert Searle attacked and plundered St. Augustine. In the aftermath of his raid and the founding of Charleston, South Carolina by the English, the Spaniards, began construction of a stone fort called Castillo De San Marcos in 1672. The walls were made of coquina, a kind of stone that had been found near the coast of Anastasia Island. This limestone formed over thousands of years from the shells of the tiny coquina clam cemented together through time and nature into a solid, but soft, stone that hardened over time. Slowly the walls rose and in August 1695, the Castillo De San Marcos, including curtain walls, bastions, living quarters, a moat, ravelin, and seawall were completed. Though St. Augustine was now very well protected, it wouldn’t stop the attacks. From South Carolina in 1702, and again, in 1728, the English descended to burn, plunder, and seize thousands of Indians for slaves. Although Castillo De San Marcos withstood artillery attacks, the hospitals, monasteries, and the valuable Franciscan library were destroyed.

Castillo de San Marcos Outer Wall

Castillo de San Marcos Outer Wall, photo by Kathy Alexander.

In 1738, the Spanish Governor Manual de Montiano at St. Augustine granted freedom to runaway British slaves and encouraged slaves to escape for sanctuary in Florida. If the fugitives converted to Catholicism and swore allegiance to the king of Spain, they were given freedom, arms, and supplies. As more and more slaves took advantage of the offer, the first legally recognized free community of ex-slaves was established. Known as Gracia Real de Santa Teresa de Mose, or Fort Mose, it was located north of St. Augustine to serve as another defense for the city.

James Oglethorpe, British founder and governor of Georgia, launched a series of attacks on St. Augustine, the most formidable in 1740, and although he failed to capture the fort, he took all the outlying defenses, including Fort Mose. His victory on St. Simon’s Island in 1742 ended the power of Spanish St. Augustine. Twenty years later, when the British took over Florida, they found a town of empty houses, as most of its residents had fled to Cuba.

Under British rule (1763-1783), St. Augustine enjoyed prosperity. The Indians were no longer a menace, great plantations were established in the area, many slave-owning English men found residence in the city, where anti-rebel sentiment was intense. John Hancock and Samuel Adams were burned in effigy in the public square, and later, prominent dissenters, including Heyward, Rutledge, and Middleton — all signers of the Declaration of Independence were imprisoned at Castillo De San Marcos.

Old City Gate, St. Augustine, Florida, by the Detroit Photographic Co., 1898

Old City Gate, St. Augustine, Florida, by the Detroit Photographic Co., 1898.

The city became an important depot for British operations against the Southern Colonies, and gunboats patrolling the coast and the St. Johns River brought in numerous American prizes. A land attack against Savannah, Georgia was launched from St. Augustine in 1777, and a naval venture in 1783 resulted in the capture of the Bahamas for England. A Tory paper, the East Florida Gazette, established here in 1783, ceased publication the year the American Revolution ended. When St. Augustine received word that Spain was again to control Florida, the British quickly evacuated. Abandoned houses gradually filled with Americans taking up Spanish land grants. A few years later, American residents urged the annexation of Florida by the United States, and in 1812, a number of them joined a similar group from Fernandina for a time to support a Republic of Florida. Another Spanish evacuation took place in 1821 when Spain sold Florida Territory to the United States (the result of the Florida Purchase Treaty of 1819). After the new American Government became operative, the second session of the legislature was held in St. Augustine, but, later, in 1824 Tallahassee was chosen as the Territorial capital.

Seminole Wars

Seminole Wars

Throughout the Seminole War, from 1835 to 1842, the city figured prominently in the national news. Soldiers wrote letters to all parts of the country, giving their impressions of the old town; of forlorn refugees from the surrounding territory camping within the walls, and of pitiful Indian prisoners and hostages confined in the dungeons of Castillo De San Marcos. Popular sentiment favored Osceola, Seminole leader, after his seizure in 1837 while en route to confer with American leaders seven miles from St. Augustine. His death in prison at Fort Moultrie, South Carolina, served to increase the bitterness, but, this and similar controversies lapsed at the close of hostilities.

Florida became a state in 1845. Following Abraham Lincoln’s election in 1860, the state joined other Southern states in declaring secession from the Union on January 10, 1861, the third of the original seven states to do so. However, it would not be for long. After only a year, the state was returned to Union control and Union troops held the Castillo De San Marcos and the town of St. Augustine from 1862 to the end of the Civil War. For a period following the war, the town was practically isolated from the rest of the state. Riverboats operated on the St. Johns River as far as Picolata, and passengers reached the city, a distance of 48 miles, after a six-hour stage and ferry trip. Provisions were mostly brought in from Jacksonville by sea, and prices were exorbitant. In 1871, a mule-drawn railroad was built from Tocoi, on the St. Johns River, to St. Augustine, but, it would be three more years before the first locomotive entered the city in 1874.

The Ponce de Leon Hotel is now Flagler College, by Kathy Alexander.

The Ponce de Leon Hotel is now Flagler College, by Kathy Alexander.

With improved transportation, an increasing number of tourists began to visit the city. Letters and articles written by noted journalists and novelists began to appear in northern papers. Among those attracted in the 1880s was Standard Oil co-founder Henry M. Flagler of New York. Impressed by the beauty of the little Spanish community, he began its development as a winter resort.

Flagler erected two large hotels, took over another to serve as the base of his Flagler System hotels, and founded the Florida East Coast Railway as a means of transporting guests to and from the north to his hotels in St. Augustine, Palm Beach, and Miami. His hotels are still in use today as Flagler College, which was once the Hotel Ponce de Leon, the Lightner Building/City Hall, which was the Alcazar Hotel, and the Casa Monica, which was redone as a county courthouse in the 1960s. In February 1997 Richard C. Kessler of The Kessler Enterprise, Inc. of Orlando purchased the Courthouse and two years later, on December 10, 1999, it was reopened as the restored Casa Monica Hotel.  It is now the only one of Flagler’s three great hotels still serving that purpose.

During these developmental years, Flagler also built or contributed to several churches, including Grace Methodist, Ancient City Baptist, and, the most ornate Venetian-style Memorial Presbyterian Church, which he built in memorial to his daughter and newly born granddaughter, who died of illness shortly after she gave birth. Flagler was so devastated by their deaths that he had the construction of the church go around the clock and finished within a year.

Oldest Wooden School in the United States.

Oldest Wooden School in the United States.

In addition to the churches, Flagler commissioned a baseball park, which became home to one of America’s pioneer professional Negro League baseball teams, the Ponce de Leon Giants; and built the city’s first hospital.

Though the large numbers of wealthy setters from the North began to alter the character of St. Augustine, the city continued to retain its quaint and romantic buildings and it unique individuality. In 1884, author George M. Barbour described the city:

“Coming to it from bustling, active, Northern-like Jacksonville or Fernandina, one is conscious of a complete and sudden change of time and place—as if the brief ride on steamer and railway had produced magic results, and landed him in some quaint, old, dead-alive Spanish town of the middle ages.”

St. Augustine, Florida Alligator Farm

St. Augustine, Florida Alligator Farm

The St. Augustine Alligator Farm, which began in the late 19th century as a small exhibition of Florida reptiles, quickly became a quintessential Florida attraction. Today it functions as a modern zoo serving the public and the scientific community with educational shows and exhibits, important research, and worldwide conservation efforts. Another early attraction enticing visitors was the Fountain of Youth, which was created in 1904. Now known as the Fountain of Youth Archaeological Park, it’s a tribute to the spot where Juan Ponce de Leon is traditionally said to have landed. The legend of the Fountain of Youth became particularly prominent in the 16th century. According to an apocryphal combination of New World and Eurasian elements, Juan Ponce de Leon was searching for the Fountain of Youth when he traveled to what is now Florida in 1513.

In the early 20th century, the rich and wealthy found other parts of Florida to which they could escape and with them, fled Flagler’s dream of turning St. Augustine into the “Newport of the South.” The city nevertheless remained a tourist town and the tourism industry came to dominate the local economy.

St. George Street, St. Augustine, Florida

St. George Street, St. Augustine, Florida

The Florida Land Boom of the 1920s left its mark on St. Augustine with the residential development of Davis Shores, on the marshy north end of Anastasia Island. Continuing on through the 20th century, many of the St. Augustine hotels were used as sites for training Coast Guardsmen during World War II, and in the 1960s was in the midst of numerous Civil Rights disputes. The city also celebrated its 400th anniversary in 1965 and undertook, in cooperation with the State of Florida, a program to restore parts of the colonial city. The continuation of an effort that actually began in 1935, what became known as the “Restoration” resulted in preserving the thirty-six remaining buildings from the colonial era and the reconstruction of some forty additional colonial buildings that had previously disappeared, transforming the appearance of the historic central part of St. Augustine.

Today, this beautiful city of about 14, 000 residents continues to provide multiple historic, cultural, and other attractions to its two million annual visitors.

© Kathy Alexander/Legends of America, updated February 2022.

Galleon ship moored at St. Augustine. Florida marina

Galleon ship moored at St. Augustine. Florida marina.

Also See:

Castillo De San Marcos – Spanish Stronghold

Florida – The Sunshine State

Fort Matanzas – Protecting St. Augustine

Haunted St. Augustine

Spanish Explorers

St. Augustine, Florida Photo Gallery


Barbour, George M.; Florida for Tourists, D. Appleton and Company, New York, 1884
City of St. Augustine, Florida
Federal Writers’ Project of the Work Projects Administration; Florida: A Guide to the Southernmost State, US History Publishers, 1939
National Park Service