St. Augustine, Florida – Oldest U.S. City
Nestled along the northeastern coast of Florida, lies St. Augustine, a city steeped in history and brimming with captivating tales. This remarkable destination holds the esteemed title of the oldest continuously occupied European-established settlement and port within the continental United States, a testament to its enduring legacy and rich cultural tapestry. From its initial exploration by Spanish conquistadors to its pivotal role in shaping American history, St. Augustine offers a unique glimpse into the past, inviting visitors to embark on a journey through time.
The narrative of St. Augustine begins with Juan Ponce de León, the Spanish Governor of Puerto Rico. On April 3, 1513, Ponce de León set foot on this land, claiming the verdant territory for the Spanish Crown. Although he only remained for a mere five days, his brief visit marked the initial European contact with the region, laying the groundwork for future colonization.
However, it would take over half a century before the Spanish established a permanent foothold. While other European powers, including the French, attempted to colonize Florida, their efforts proved unsuccessful. It was not until September 8, 1565, that Spanish Captain Pedro Menéndez de Avilés arrived, marking a turning point in the region’s history. Sailing through the St. Augustine Inlet into Matanzas Bay, Menéndez, accompanied by 1,500 soldiers and colonists, disembarked near the Timucuan Indian village of Seloy. This expedition also brought the first enslaved Africans to what would eventually become the United States.
Taking possession of the territory along the river, Menéndez established a settlement, christening it St. Augustine in honor of St. Augustine’s Day, a Catholic holiday celebrated on August 28, the day he first sighted Florida.
Menéndez’s immediate objective was to construct a rudimentary fortification to safeguard his people and provisions as they were unloaded from the ships. Following this initial step, he intended to conduct a thorough survey of the area to determine the most suitable location for a permanent fort.
Meanwhile, French Captain Jean Ribault had embarked on his own mission to resupply the French outpost of Fort Caroline, located in present-day South Carolina. Upon learning of Menéndez’s arrival in Florida, Ribault, driven by a desire to eliminate the Spanish presence, set sail with his men on September 10 to attack St. Augustine. However, fate intervened in the form of a fierce hurricane, which swept Ribault’s ships far to the south, ultimately wrecking them along the Florida coast between modern-day Daytona Beach and Cape Canaveral.
Seizing this opportunity, Menéndez led a force to attack Fort Caroline. With the majority of French soldiers absent, Menéndez easily captured the settlement, resulting in the deaths of most of the men. However, some inhabitants, including René de Laudonnière, the founder of Fort Caroline, and the artist Jacques LeMoyne, managed to escape aboard ships and return to France. Menéndez spared the women and children, sending them by ship to Havana.
Following his victory at Fort Caroline, Menéndez received intelligence from the Timucuan Indians regarding a group of white men stranded on the beach a few miles south of St. Augustine. Accompanied by 70 soldiers, Menéndez marched to the location, where he encountered 127 shipwrecked Frenchmen attempting to return to Fort Caroline, their path blocked by an inlet. Employing a captured Frenchman as a translator, Menéndez informed the Frenchmen of the capture of Fort Caroline and urged them to surrender. Despite conflicting accounts, Menéndez reportedly made no explicit promises to spare their lives. Having lost the majority of their food and weapons in the shipwreck, the Frenchmen surrendered. However, when Menéndez demanded that they renounce their Protestant faith and embrace Catholicism, they refused. Ultimately, 111 Frenchmen were executed, with only 16 spared – a few claiming to be Catholic, some impressed Breton sailors, and four artisans deemed necessary for the survival of St. Augustine.
Two weeks later, a similar scenario unfolded. More French survivors appeared at the inlet, among them Jean Ribault. On October 12, Ribault and his men surrendered, meeting the same fate as their comrades after refusing to renounce their faith. This time, 134 were killed. The inlet was subsequently named Matanzas, meaning "slaughters" in Spanish, a somber reminder of the tragic events that transpired there.
St. Augustine ascended to become the capital of Florida and the Spanish military headquarters of North America. For the next four decades, its governors oversaw forts and patrolled the coastline stretching from Virginia to Florida, thwarting attempts by other nations to establish colonies within the territory. In 1586, British Admiral Sir Francis Drake launched a formidable attack on St. Augustine, sacking and burning the town. The Spanish colonists sought refuge in the forests during the raid, but later returned to rebuild their homes.
As the headquarters of missionary activities among the southeastern Indians, St. Augustine gained further strategic importance. Through its network of 40 or more mission towns, it exerted control over the natives and defended the frontier against French and English incursions. Nevertheless, it remained a tempting target for aggressors. In 1668, English privateer Robert Searle attacked and plundered St. Augustine. In response to this raid and the English establishment of Charleston, South Carolina, the Spanish initiated the construction of a stone fort in 1672, known as Castillo De San Marcos.
The walls of Castillo De San Marcos were constructed from coquina, a unique type of stone found near the coast of Anastasia Island. This limestone, formed over millennia from the shells of tiny coquina clams cemented together by time and nature, possesses a solid yet soft texture that hardens over time. Gradually, the walls rose, and in August 1695, the Castillo De San Marcos, complete with curtain walls, bastions, living quarters, a moat, ravelin, and seawall, was finished. St. Augustine was now heavily defended, but the attacks did not cease entirely. In 1702 and again in 1728, the English descended from South Carolina, burning, looting, and enslaving thousands of Indians. Despite enduring artillery attacks, Castillo De San Marcos stood firm, although the hospitals, monasteries, and the valuable Franciscan library were destroyed.
In 1738, the Spanish Governor Manuel de Montiano in St. Augustine made a momentous decision, granting freedom to runaway British slaves and encouraging others to seek sanctuary in Florida. Fugitives who converted to Catholicism and swore allegiance to the King of Spain were granted freedom, arms, and supplies. As increasing numbers of slaves embraced this opportunity, 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 situated north of St. Augustine and served as an additional layer of defense for the city.
James Oglethorpe, the British founder and governor of Georgia, launched a series of attacks on St. Augustine, the most significant in 1740. While he failed to capture the fort, he seized all the outlying defenses, including Fort Mose. His victory on St. Simon’s Island in 1742 marked the decline of Spanish power in St. Augustine. When the British assumed control of Florida 20 years later, they found a town largely abandoned, as most of its residents had fled to Cuba.
Under British rule (1763-1783), St. Augustine experienced a period of prosperity. The threat from the Indians diminished, large plantations flourished in the area, and many slave-owning English families took up residence in the city, where anti-rebel sentiment was strong. John Hancock and Samuel Adams were burned in effigy in the public square, and later, prominent dissenters, including Heyward, Rutledge, and Middleton – all signatories of the Declaration of Independence – were imprisoned at Castillo De San Marcos.
The city transformed into a crucial 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 assault against Savannah, Georgia, was launched from St. Augustine in 1777, and a naval expedition in 1783 resulted in the capture of the Bahamas for England. The Tory paper, the East Florida Gazette, established here in 1783, ceased publication the year the American Revolution ended.
Upon receiving news that Spain would once again control Florida, the British swiftly evacuated St. Augustine. Abandoned houses gradually filled with Americans taking advantage of Spanish land grants. Several years later, American residents advocated for the annexation of Florida by the United States, and in 1812, some joined a similar group from Fernandina in supporting the Republic of Florida for a time. Another Spanish evacuation occurred in 1821 when Spain sold Florida Territory to the United States (the result of the Florida Purchase Treaty of 1819). Following the establishment of the new American government, the second session of the legislature was held in St. Augustine, but in 1824, Tallahassee was chosen as the Territorial capital.
Throughout the Seminole War, from 1835 to 1842, St. Augustine played a prominent role in national news. Soldiers wrote letters to all parts of the country, sharing their impressions of the old town, the forlorn refugees from the surrounding territory camping within the walls, and the pitiful Indian prisoners and hostages confined in the dungeons of Castillo De San Marcos. Popular sentiment favored Osceola, the Seminole leader, after his capture in 1837 while en route to confer with American leaders seven miles from St. Augustine. His death in prison at Fort Moultrie, South Carolina, heightened the bitterness, but this and similar controversies subsided at the close of hostilities.
Florida achieved statehood 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, becoming the third of the original seven states to do so. However, this separation was short-lived. After only a year, the state was returned to Union control, and Union troops occupied Castillo De San Marcos and the town of St. Augustine from 1862 until the end of the Civil War. The town was effectively isolated from the rest of the state following the war. 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 primarily brought in from Jacksonville by sea, resulting in exorbitant prices. In 1871, a mule-drawn railroad was constructed from Tocoi, on the St. Johns River, to St. Augustine, but it would be another three years before the first locomotive entered the city in 1874.
With improved transportation, more tourists began to visit the city. Articles and letters written by noted journalists and novelists started appearing in northern newspapers. Among those drawn to St. Augustine in the 1880s was Henry M. Flagler, co-founder of Standard Oil. Captivated by the beauty of the small Spanish community, he initiated its development as a winter resort.
Flagler erected two grand hotels, acquired another to serve as the base of his Flagler System hotels, and established the Florida East Coast Railway to transport guests to and from the North to his hotels in St. Augustine, Palm Beach, and Miami. His hotels continue to serve new purposes 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 converted into 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 remains the only one of Flagler’s three great hotels still serving its original purpose.
During these developmental years, Flagler also built or contributed to several churches, including Grace Methodist, Ancient City Baptist, and the ornate Venetian-style Memorial Presbyterian Church. He commissioned the church in memory of his daughter and newly born granddaughter, who both succumbed to illness shortly after the birth. Flagler was so deeply saddened by their deaths that he had the church constructed around the clock, completing it within a year.
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.
While the influx of wealthy settlers from the North began to alter the character of St. Augustine, the city retained its quaint and romantic architecture and 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."
The St. Augustine Alligator Farm, which began in the late 19th century as a small exhibition of Florida reptiles, rapidly evolved into a quintessential Florida attraction. Today, it serves both the public and the scientific community as a modern zoo, offering educational shows and exhibits, supporting important research, and engaging in worldwide conservation efforts. Another early attraction enticing visitors was the Fountain of Youth, established in 1904. Now known as the Fountain of Youth Archaeological Park, it stands as a tribute to the spot where Juan Ponce de León is traditionally believed to have landed. The legend of the Fountain of Youth gained prominence in the 16th century. According to an apocryphal tale combining New World and Eurasian elements, Juan Ponce de León was searching for the Fountain of Youth when he journeyed to what is now Florida in 1513.
In the early 20th century, the wealthy discovered other parts of Florida to which they could escape, and with them, Flagler’s dream of transforming St. Augustine into the "Newport of the South" faded. The city remained a tourist destination, with the tourism industry dominating the local economy.
The Florida Land Boom of the 1920s left its imprint on St. Augustine with the residential development of Davis Shores on the marshy north end of Anastasia Island. Throughout the 20th century, many of the St. Augustine hotels were utilized as training sites for Coast Guardsmen during World War II. In the 1960s, the city was at the center of numerous Civil Rights disputes. St. Augustine also celebrated its 400th anniversary in 1965 and, in cooperation with the State of Florida, undertook a program to restore parts of the colonial city. Continuing an effort that began in 1935, the initiative, known as the "Restoration," resulted in the preservation of the 36 remaining buildings from the colonial era and the reconstruction of approximately 40 additional colonial buildings that had previously disappeared, significantly transforming the appearance of the historic central part of St. Augustine.
Today, this captivating city, home to over 14,000 residents, continues to offer a wealth of historical, cultural, and other attractions to its two million annual visitors.