Most people who have gone through schools in the United States have a skewed view of the Underground RailRoad which was neither a railroad nor underground. As effective as it may have been, it was a long walk from the slave states close to the Mason Dixon line that took constant vigilance watching for those hoping to cash in on a bounty, and faith in the people you were supposed to meet up ahead. It was also limited in coverage as the longer the journey the less likely the success, and failure meant being sent further down south where the OGRR did not have tracks.
We have all the stories about the secret meanings of Negro Spirituals, are familiar with Harriet Tubman even if it is to protest her replacing Andrew Jackson on the twenty, and a lot of movies with uplifting endings.
The Underground RailRoad we were taught about took place close to the North/South Border and went straight up to Canada by way of the inland states.
To affect an escape, there had to be a chain of people to give the correct signal at the right time, people arranged along the way to supply the travelers’ needs, and ways to guard against the possibility that bounty hunters will be able to track you down. It was a system under the control of a lot of people but not the person ready to leave. He or she had to wait for others to start their future.
After days of traveling, an escape to the free states did not mean you were free as you could easily be followed and brought back most likely to be sold deeper south.
The part of the Underground Rail Road that is overlooked is the most obvious. Just looking at a map, it is clear that from Maryland, around Florida to the Gulf of Mexico there are thousands of miles of seacoast and in places like the Chesapeake Bay, with all its inlets and smaller bays, even more coastline where colonies, then states, built seaports to which what was produced inland was brought to be shipped all over the globe. This system brought agrarian slaves into cities and smaller towns on rivers and estuaries where they could mingle with other Blacks, slave and free, and learn about places and things so far removed from the plantations.
Seaports needed people to fix and repair ships, fit ships out for voyages, and load and offload them. Whole cities were based on the ports with the majority of businesses having some connection to the docks.
There was plenty of hard work to be done related to shipping, and in the South that work was done by slaves who were not only learning a trade, but networking to find a way out and who would then take those trades and get employment when they got to a sanctuary city, like Frederick Douglass did.
Slaves knew schedules of ships, who was policing where on a regular basis, who the sympathetic captains might be, or the ones who would be less likely to find a stowaway. They also knew every inch of every ship they worked on in port and, so, knew the best places to hide.
And as they became familiar to the other workers and some of the sailors who came to port regularly as part of a regular run, they found allies who would aid and cover for them.
It was an action that required intelligence to get to the point that a disappearance would not be immediately known and often was, after the ship had sailed and was out to sea.
The three days from the most Southern port on the East Coast to the first Northern and, therefore, safe port was a lot shorter than an overland trip, and, unless they had come up with a fast boat, bounty hunters would not be following.
Riding the winds and currents made turning back to turn in a stowaway out of the question, so the completion of the trip was guaranteed, what happened after reaching port was not.
For bounty hunters to bring you back it would mean a long trip up North dealing with abolitionists when they got to the city to which they assumed the self-emancipated person had gone and putting up with purposeful misdirection and other machinations to keep bounty hunters away from the new Northern residents, followed by a long trip back with the fugitive and the possibility of another escape and either going on another chase or return empty-handed and not get paid.
There are many examples of maritime emancipations, the ships that took people North, and the captains who made the escapes possible, or who, upon finding they had a stowaway on board, handled it so they both followed and violated the law so they were covered and the slave now free.
For those with an interest in the Underground Rail Road, the Maritime version is worth looking into. Maritime emancipation dispels the old notion of slaves not being all that intelligent when the facts of these emancipations showed how intelligent and clever these people, men and women, and in some cases children, were to have learned the system and played it well.