In Florida, the Underground Railroad Ran SouthIt traveled on the historic Old Kings Road.

Florida had long been a place of refuge. During the first Spanish period, the King even encouraged escaping slaves to come to Florida under the “Kings Edict.”

 (A PowerPoint slide presentation by William Ryan on June 21, 2012, at the 2012 National Underground Railroad Conference – St. Johns County Convention Center – St. Augustine Florida sponsored by African American Experience Fund of the National Park Service)

Based on the book “Osceola his capture and Seminole legends” by William Ryan

Florida had long been a place of refuge. During the first Spanish period, the King even encouraged escaping slaves to come to Florida under the “Kings Edict.” This offered families freedom if they would convert to Catholic and pledge allegiance to the King. It is true that the King of Spain was trying to anger the English but the effect was to offer hope in Florida. The Spanish also had a complex series of “slave codes” whereby a person of color had certain rights under the law, eg. He could own property, or even buy his own family’s freedom. In 1683 free blacks and mulattos were organized into armed militia companies to protect St. Augustine.

So for some 200 years under Spanish rule, wild and largely unsettled Florida became a place of refuge.

In 1738 a black militia was formed with a fort near St. Augustine. It was called “Gracia Real de Santa Terese de Mose or Fort Mose. In 1740 black Captain Francisco Menendez fought a successful battle against the raiders from Georgia. Long before the Civil War and the Underground Railroad black families were finding freedom and reward in Florida. The site of the old settlement is now a historic spot in St. Augustine.

When the British took over Florida in 1763, after the French and Indian War, slaves still would escape here, as Florida was mostly unpopulated. The black settlers were called Maroons. The British built The Old Kings Road just prior to the American Revolution. They knew a good road was needed in order to bring settlers to Florida. This amazing road ran from Georgia to the new colony at New Smyrna Florida. It was the main entry into Florida right up to 1914. It also was a primary route for black families to escape to freedom in the wilds of Florida.

When the British arrived, many of the free blacks and slave families in St. Augustine had departed with the Spanish. They settled in Cuba. Under Spanish rule, St Augustine had many tradesmen and skilled workers who were free people of color Many had sailed away with the Spanish.

From 1771 to 1777 the British established several large plantations along Old Kings Road. These were built with slave labor and maintained by slaves growing sugar cane, cotton, and Indigo. The British would be in Florida until 1784 when they would depart following negotiations in Paris to settle the U.S. Revolutionary War. The Spanish would return under agreements worked out with Benjamin Franklin and others.

In 1787 the Spanish issued land grants along the still existing Old Kings Road hoping to repopulate Florida. By 1784 there were again black refugees escaping into Florida with Old Kings Road still a primary routing into Florida. By 1821 when the Spanish departed Florida there were several large plantations located along Old Kings Road, built by slave labor. When the Americans took over Florida many more settlers located along Old Kings Road and the slave population of Florida increased.

Florida was still a wild place. Thus there were former plantation slave workers who escaped to Florida from the north, fled down the Old Kings Road and in some instances settled with the Seminole Indians. Also, black towns and plantations had long existed on the Western side of Florida. The Spanish had established fishing camps in the area. Also, the gulf coast of Florida was the route for the Creek Indians in their summer hunts into Florida. There was a great mixture of peoples along the Gulf Coast. Spanish fishermen and traders still came here. Free black families lived along the Gulf Coast area.

Many of the Seminoles were cattlemen. The Chiefs also owned slaves but the relationship was said to be different, often more like an indenture agreement than what we would associate with the practice of slavery on the Georgia or Carolina plantations. Again small family groupings existed in Florida, known black villages, populated by free men. Typical was “Negro Town” with the Seminole Chief Coa Hadjo. The first U.S. cowboys were most certainly either slaves or free blacks often working for a Seminole chief. The Seminole Indians were known to have large herds of Spanish cattle. Black families frequently had their own village, related to, but separate from their Seminole Chief.

Affairs changed dramatically when the U.S. agreed to take over Florida from the Spanish in 1819. Andrew Jackson had made several unauthorized raids into Florida taking control of Spanish territory. In 1821 the Spanish finally gave up and for a second time departed from Florida. Soon slave raiding into Florida became active from Georgia and the Carolinas. One such raid was in Angola a black settlement on the Gulf Coast. Angola was located on the Manatee River which is present-day Bradenton. Jackson was accused of sending hired and paid Coweta Indians with some white half breed officers to capture and sell any person of color. There were endless raids of individual groups coming into Florida to capture “blacks” for sale. The definition of who was a person of color was a thin one. Some of the Indians had dark skin or had family members through several generations of intermarriage to offer darker complexions. Some full-blooded Seminole Indians had dark skin by nature. Because the import of slaves was now forbidden into the U.S. the gold price of a slave rose to the amazing cost of $1000 back in 1821. This was a huge amount of money and fortunes were being made by those raiding into Florida. Who was black and who was Seminole was not always acknowledged by the raiders. (1)

 (1)” A class of people neither freemen nor slaves “: from Spanish to American race relations in Florida, 1821-1861 by Daniel L. Schafer) 

As a result of the slave raids, the black communities were now in a panic to escape from Florida. Some of the Angola peoples reportedly fled to Andros Island, other places in the Bahamas and south to the Florida Keys. Spanish fishing boats provided some with transport, others reportedly used canoes.

Also in 1823, the Seminole Chiefs were forced into the treaty of Moultrie making them surrender some 4 million acres of prime land in Florida which they had claimed to be theirs. They would be moved to a reservation in central Florida that was acknowledged to be bad land. The Seminole nation would be reduced from wealth and a stable relationship with their black friends to poverty and hunger on a government reserve. While the agreement provided for the faith of the U.S. government to protect them against raiders upon their new lands, soon it was found that this was not to be true. Other treaties and invasions by the whites hungry for new lands in Florida brought never-ending conflicts to the Seminoles, who often now were hungry and destitute in their new reservation. The “Black Seminoles” or the sons and daughters of slaves who had escaped into Florida long ago were in a similar desperate condition.

Osceola was a young Seminole Indian whose family had fled into Florida by the nearly endless wars and raids in Georgia by Jackson and others. He was not a chief after many events the Seminoles were desperate. They were losing their lands to the whites, they were being constantly raided, and their black friends or relatives were being taken and sold into slavery. They had no other decision than to fight.

On Christmas Eve 1835 the war began and this terrible Viet Nam type war would last for seven years. It was reported that slaves on many of the plantations were told that something would happen on Christmas. Later it would be said that the Seminoles “captured” slaves, but later accounts would state that many joined with the Indians with the will and became fierce soldiers in the fight.

This would soon become the largest slave uprising in the history of the United States. The previous Nat Turner slave revolt in August of 1831 had caused great anger in the South. Fifty-six people were murdered by Turner and his group. The resulting panic caused the deaths of thousands of innocent Negroes in the South as militia groups took revenge.

The Seminole War began near Christmas 1835. The Army later was frantic to separate the escaped black slaves and the “Black Seminoles” from the Indians. They tried many tricks. In 1836 U.S. General Thomas Jesup had written “this is a negro war, not an Indian war

Eventually, some were captured and sent west with their Seminole owners

Some escaped by joining with the Spanish gun runners and went to the Islands and also to Cuba. (It is interesting that many years later their decedents may have been the supporters of Fidel Castro.) Osceola was not a chief. He was a war leader and took part in two early battles. He led in many other Vietnam type engagements. It was a brutal, desperate war in a terrible place. Perhaps more soldiers died from disease and the climate rather than from Indian bullets. However, many chiefs did not favor the war and blamed Osceola as an agitator. He had murdered Charley Emathla, an old, well-liked chief who did not favor conflict with the whites. Osceola’s active followers included Black Seminoles and escaping blacks. These men would fight to the death. Some accounts of the times wrote that one of Osceola’s two wives was black but this has never been verified.

The details of Osceola’s struggle and the Seminole War leading to his capture under a white flag of truce on Old Kings Road are contained in William Ryan’s book “Osceola His Capture and Seminole Legends.”

(2) A well-researched internet site exists on the Black Seminoles or Maroons at

Osceola’s followers included John Horse a black Seminole who probably came from the Angola area. He also was accompanied by Coa Hadjo who was the Chief of “Negro Town” in South Western Florida who may have been black or had a colored wife.

In time the army had destroyed all food stocks. The escaped slaves were starving, their families were desperate. King Philip, the leader of the Seminoles on the east coast had been captured and held in the fort in St. Augustine. In an agonized decision Osceola had agreed to return some of the escaped slaves. An army food cache was made for the starving slaves at Pellicer Creek. (3) Osceola’s s small group went north on Old Kings Road under a white flag of truce to meet with the army. There were some 60-80 in his party. It was reported that the two sons of John Hicks former Seminole leader were with him, in addition to John Horse and a group of black warriors. The army sent some 200 mounted soldiers led by General Hernandez down Old Kings to capture him. The army soldiers did meet the small group of former slaves now going north on Old Kings Road. They knew that Osceola had kept his promise even before they met and captured him on a pretext that he had failed to do so.

Osceola was captured and sent to the fort at St. Augustine

His later death in a fort at Charleston was well documented and accounts were read throughout the world. His struggle had an effect on enabling the escape of many black families. It forced the General Jesup to negotiate an agreement on “Seminole property” that sent many Maroons and black families to a new, but uncertain life in the American West.

The old British Old Kings Road was truly part of the “Railroad that ran South”

(2) Osceola His Capture and Seminole Legends William Ryan Old Kings Road Press Flagler Beach FL

(3)  Letters of Samuel Flory, Surgeon U.S. Army 1837-1838 Written to Lt  J.W. Phelps, Black Creek St Augustine Oct 19th 1837

The Search for Old Kings Road” details the efforts to find and preserve this old road that played so much a part in Florida’ s history .

What became of the slaves in Florida?

1. Some escaped to Cuba and the Islands

2. Some made it to Indian Territory in the West and later fought for the Mexican government against the Texans. After the Civil War ended they would become the famous “Black Seminole Scouts” for the U.S. army..

3. Many were re-captured and sold back into slavery .

The new U.S. government and local governments now passed a series of “Slave Laws” which destroyed all rights of black people. No longer had the negro they any standing in law. Everyone had to have an owner or master. (this was not true under the Spanish or the British) The effect of these laws made slavery in the South stronger, yet increased the agitation for settlement in nonslave states and from those opposed to slavery in the United States.

During the Civil War in which Old Kings Road again played an important part as still being the main roadway from and into Florida. Old Kings Road was the routing to the north for cattle herds sent to feed the Confederate Army, and supplies of much-needed salt from Florida. Again the black cowboys of Florida played a major role in this effort. (see Florida Agricultural Museum Black Cow Boy display}

William Ryan

October 25, 2010 – revised October 8, 2011

Complete listing of references appears in:

Search for Old Kings Road

I am Grey Eyes

Osceola His Capture and Seminole Legends

Author: Bill Ryan