The Southbound Underground Railroad

By David A. Carrino, Roundtable Historian
The Cleveland Civil War Roundtable
Copyright © 2016-2017, All Rights Reserved

Editor’s note: This article was the history brief for the May 2017 meeting of the Cleveland Civil War Roundtable.

The Civil War has been called the first modern war, because many innovations that had been developed in the years prior to the Civil War saw their first extensive wartime use in the Civil War. In keeping with this, the January 2004 Cleveland Civil War Roundtable Dick Crews Debate focused on the topic of the equipment or innovation that had the most effect on the Civil War. One of the five innovations that were discussed was railroads. Most historians agree that the Civil War was the first war in which railroads saw widespread use and had a major impact. For example, at the First Battle of Bull Run, Joseph Johnston used a railroad to rapidly move his troops from the Shenandoah Valley to reinforce P.G.T. Beauregard. A few months after the Battle of Shiloh, Braxton Bragg moved his infantry by rail along a circuitous route from Tupelo, Mississippi to Chattanooga, Tennessee so he could join forces with an army led by Edmund Kirby Smith for an invasion of Kentucky. Railroads were instrumental prior to the Civil War in the development of the United States due to their capacity for rapid transportation in all directions throughout the country. However, there was one pre-Civil War railroad that operated in only one direction. This railroad, which operated without locomotives and without tracks and was a railroad in name only, was the Underground Railroad, and it went essentially only in a northbound direction.

As Civil War enthusiasts know, the Underground Railroad was a series of secret routes by which escaped slaves fled from slave states to free states. The Cleveland Civil War Roundtable visited the Underground Railroad museum in Cincinnati several years ago as part of our annual field trip. Because of the geographic locations of free and slave states, escaped slaves who used the Underground Railroad moved northward, which is where they could find freedom. However, before there was a northbound Underground Railroad to move escaped slaves toward freedom, there was a southbound Underground Railroad that moved escaped slaves toward freedom. In fact, this southbound Underground Railroad was the first Underground Railroad that was used by escaped slaves to flee from the future Confederacy in a quest for freedom.

Pedro Menéndez de Avilés

The story of the southbound Underground Railroad revolves around what is considered the oldest city in the United States: St. Augustine, Florida. St. Augustine was founded on September 8, 1565 by Spanish admiral and explorer Pedro Menéndez de Avilés. St. Augustine, which is in northeast present-day Florida, was the capital of the Spanish territory of Florida. The original contract with the Spanish crown stipulated that 500 slaves would be brought to St. Augustine to work on sugar plantations, but none of the slaves called for in the contract was ever brought to the settlement. Spain’s system of slavery, which was in place for centuries before Spain’s colonization of the New World, differed from that of Britain. Spanish slaves had some rights, such as the right to own property and to purchase their freedom, and it was illegal to separate members of a slave family. Although the life of a Spanish slave was by no means desirable, it was preferable to that of a slave in the British system of chattel slavery.

North of Spanish Florida the British brought captured Africans to work as slaves in their North American colonies beginning with the arrival of 20 African slaves in August 1619 in Jamestown. When the British established present-day Charleston, South Carolina in 1670, African slaves were brought with them, and during the 17th and 18th Centuries many African slaves worked on plantations in the Carolinas. In 1687 the Spanish colonial governor in St. Augustine, Diego de Quiroga, reported to the home country that 11 escaped slaves from the Carolinas, eight men, two women, and a three-year-old nursing child, arrived in St. Augustine. These were the first recorded escaped slaves from a British colony to flee to Spanish Florida. Quiroga decided that the slaves were not to be returned to their owner, but would be allowed to remain in St. Augustine, if they agreed to accept the Catholic faith and declare loyalty to Spain. It is not clear how slaves in the Carolinas learned of a better life in St. Augustine, or if they even knew of this, but simply journeyed in whatever direction they could away from the Carolina plantations. A year before these escaped slaves made their way to Spanish Florida, tensions between Spain and England over their colonial territories in North America led to a raiding party from Spanish Florida attacking some British settlements in the Carolinas and removing, among other possessions, 13 slaves. The British governor of Carolina, James Colleton, demanded the return of not only those 13 slaves, but also those slaves “who run dayly into your towns,” which suggests that there had been previous and numerous slave escapes from the Carolinas into Spanish Florida. The Spanish refused to return those slaves, and perhaps knowledge of this somehow made its way to the slaves in the Carolinas, who now knew of an escape route to freedom, an escape route that went south.

King Charles II

Whether or not escaped slaves knew that southward was the direction for possible freedom, the Spanish crown recognized that keeping escaped British slaves was a way to aggravate its rival, England. Moreover, in 1683, four years before the recorded arrival of those 11 escaped slaves, the Spanish colonial government organized a militia composed of free black men to help defend against any British incursions. To further torment the British, on November 7, 1693 King Charles II of Spain issued a decree regarding escaped slaves, in which he stated that he was “giving liberty to all…the men as well as the women…so that by their example and by my liberality others will do the same.” In succeeding years four groups of escaped slaves were recorded as arriving in St. Augustine, and there were probably more than this based on known complaints by the British governor of Carolina to the home country. In 1724 a group of ten escaped slaves arrived in St. Augustine and claimed to have known that their freedom was guaranteed by the king of Spain if they converted to Catholicism. In addition, these escaped slaves had been assisted on their journey by Yamassee Indians, who had earlier fought a war with British colonists and, hence, were not on friendly terms with the British.

Map, from a 1762 book, showing the location of Fort Mose (“Negroe Fort”) relative to St. Augustine
A drawing of Fort Mose

Due to the growing population of blacks in St. Augustine, in 1738 the Spanish governor, Manuel de Montiano, decided to allow the blacks of St. Augustine to establish a separate settlement two miles north of the city. This decision was not made solely for altruistic reasons, because Montiano saw the black settlement as a first line of defense against a British attack. The settlement was named Gracia Real de Santa Teresa de Mose (pronounced Moe-zay, with the accent on the second syllable). At the center of the settlement was a fort, Fort Mose, which was surrounded by dwellings for the people of the settlement. The land in the area was fertile, and farming provided food for the residents of Mose. It was clear that the free black men of Mose, who were members of a militia, understood that the freedom to settle in their own town came with a commitment, because they pledged to be “the most cruel enemies of the English” and to spill their “last drop of blood in defense of the Great Crown of Spain and the Holy Faith.” Obviously this pledge was also beneficial to themselves, since resisting the British meant resisting a return to chattel slavery.

A depiction of the confrontation between Julio León Fandiño and Robert Jenkins
James Oglethorpe

In 1740 the Mose militia had an opportunity to follow through on its pledge. In January of that year James Oglethorpe, the British governor of Georgia, led an invasion into Spanish Florida in response to numerous slave escapes and some slave insurrections, all of which the British believed were instigated by the freedom offered in St. Augustine. Oglethorpe’s invasion was part of a larger conflict between Britain and Spain that is known as the War of Jenkins’ Ear. The name refers to an incident that occurred off the coast of Florida eight years before hostilities began. A boarding party from a Spanish patrol boat went aboard a British merchant ship, and the captain of the Spanish boat, Julio León Fandiño, became engaged in a heated exchange with Robert Jenkins, the captain of the British ship. Fandiño accused Jenkins of smuggling and in a fit of rage cut off Jenkins’ ear. Jenkins was called before Parliament to give his account of the incident, during which he reputedly showed the severed ear. Numerous hostile boardings of British ships by the Spanish coupled with Britain’s desire to improve its trade in North America by weakening its chief rival led Britain to go to war with Spain. Georgia Governor James Oglethorpe was more than willing to engage in a conflict with the Spanish colonists of Florida, whom he blamed for provoking slave escapes and revolts. Oglethorpe’s invasion force captured some Spanish outposts west of St. Augustine and eventually threatened the city, itself. Governor Montiano feared that Mose could not withstand an attack by the overwhelming British force, so he evacuated all of the people of Mose into the fortifications of St. Augustine, to which Oglethorpe laid siege after capturing Fort Mose. On June 15, 1740 a force that included Spanish soldiers and the Mose militia attacked the British-occupied Fort Mose. The surprise attack commenced prior to dawn, before the British soldiers were awake, and the fort, after a vicious hand-to-hand fight, was taken from the British, who lost 70 men killed in the battle. Primarily because of this setback, Oglethorpe ended the siege of St. Augustine and retreated to Georgia.

A depiction of the Battle of Fort Mose

After the War of Jenkins’ Ear, Spain retained control of Florida. Mose was destroyed during the fighting between the British and the Spanish, and the Mose residents lived for a time in St. Augustine. Mose was eventually rebuilt, although on a different site, and the free blacks occupied the rebuilt settlement in 1752, but there is some evidence that the blacks resisted the relocation and desired to remain in St. Augustine. The governor at that time, Fulgencio García de Solís, claimed that this resistance among the blacks was not due to fear of living in a less defensible location, but due to their desire to live in “complete liberty.” In other words, after living for 12 years within St. Augustine, the free blacks preferred assimilation into the city’s population rather than their own separate town. In spite of the wishes of the free blacks, they were forced to live in the rebuilt Mose. As part of the treaty after the Seven Years’ War, Spain ceded Florida to Britain in 1763, and Spanish residents of Florida, including the free blacks of Mose, moved to Cuba. This brought an end to the free black settlement of Mose and to the southbound Underground Railroad. In 1784, as part of the agreements that ended the Revolutionary War, Spain regained control of Florida. During the second period of Spanish control of Florida, escaped slaves again migrated there for freedom, but there is no evidence that the town of Mose was reestablished. In addition, many white settlers from the U.S. moved into Florida, and Florida became a haven for slave smugglers, who brought in slaves, mostly from Cuba, but some from Africa, to sell in the U.S., primarily in Georgia. After the War of 1812 there were incursions from the U.S. into Florida, some by civilians and militiamen and some by U.S. troops. Eventually Spain came to realize that it could not maintain control of Florida, and Spain ceded Florida to the U.S. Thereafter slavery was established in Florida by the U.S., and Florida was no longer a destination for escaped slaves.

A quote attributed to Horace Greeley (although there is some question as to whether he is the originator of the quote) gave directional advice to those who were seeking a better life. According to this quote, the way to go, in a geographic sense, was west. Although going west may have been good advice for some people who were seeking a better life, west was not the preferred direction for escaped slaves who were seeking a better life in freedom via the Underground Railroad. For those escaped slaves, north was the way to go. But before the northbound Underground Railroad existed, there was a southbound Underground Railroad, and this was the first Underground Railroad that was used by escaped slaves to flee from the future Confederacy and find freedom.

Related link:
The Underground Railroad in Ohio