Frederick Douglass: The Sailor You Should Know

By: Sailing History

In October of 2021, I sailed on the Chesapeake Bay on an American Sailing Charter. As with all of these charters, I am fortunate enough to meet many great people who love to sail. We anchored in Cambridge, Maryland, on this particular charter and went ashore. I am almost embarrassed to admit to this, but I never really understood the history of this area. Unfortunately, American history often dilutes the important stories ingrained in our geography. We know something about North and South, but on this day, on the Choptank River, just off the Chesapeake Bay, I learned so much about the history of slavery and the region.

A passenger I had just met a couple of days before explained that there was a Harriet Tubman Museum in Cambridge. She gave me a quick rundown of the architecture and history of the area. I was fascinated and was looking forward to visiting the museum. Unfortunately, as is often the case when sailing, the wind and weather did not cooperate, and the museum was closed by the time we set foot in Cambridge. So instead, I went off to a restaurant and had some delicious Maryland crab cakes and struck up a conversation with another person dining alone. I learned so much about the history of Maryland and its role in freedom for slaves from the south over a beer and some crab cakes. 

In his autobiographies, Frederick Douglass takes us through a narrative of his time in the Chesapeake region, and he illustrates a bit about the soul of a sailor. Of course, we don’t always associate Douglass as a sailor. Still, suppose there was ever a figure that exemplifies that ability to escape in sailing. In that case, it is the story of Frederick Douglass’ life and his association with ships, sailing, and the Chesapeake Bay.

The Sailor You Should Know

Frederick Douglass is well known in American history as an escaped slave who became a prominent figure in the abolitionist movement and civil rights activist. His autobiography Narrative of the Life of Frederick Douglass, an American Slave is often referred to as an inspiration for the civil rights movement of the 1960s. What is not often spoken about is that Frederick Douglass was a sailor. Maybe not by choice but definitely out of necessity.

In his autobiography, Douglass describes the sloop Sally Lloyd that while Captained by his master’s son in law was manned by his master’s slaves. The slaves, named Peter, Isaac, Rich and Jake were “esteemed very highly by the other slaves, and looked upon as the privileged ones of the plantation…

If not for the fact that Douglass is narrating the captive life of a slave his words eloquently describe sailing much like we all do when we set sail.

At between seven and eight years old he recalled:

“We sailed out of Miles River for Baltimore on a Saturday morning. I remember only the day of the week, for at that time I had no knowledge of the days of the month, nor the months of the year. On setting sail, I walked aft, and gave to Colonel Lloyd’s plantation what I hoped would be the last look. I then placed myself in the bows of the sloop, and there spent the remainder of the day in looking ahead, interesting myself in what was in the distance rather than in things near by or behind.”

Douglass describes leaving the plantation for Baltimore at a young age much like sailors describe their own release from the world they exist in when aided by a sailboat as a means of escape:

“I prefer to be true to myself, even at the hazard of incurring the ridicule of others, rather than to be false, and incur my own abhorrence. From my earliest recollection, I date the entertainment of a deep conviction that slavery would not always be able to hold me within its foul embrace; and in the darkest hours of my career in slavery, this living word of faith and spirit of hope departed not from me, but remained like ministering angels to cheer me through the gloom.”

Upon being taken from a family in Baltimore back to the country in St. Michaels. Sailing once again aided in continuing his desire to find a way to escape:

“I sailed from Baltimore for St. Michael’s in the sloop Amanda, Captain Edward Dodson. On my passage, I paid particular attention to the direction which the steamboats took to go to Philadelphia. I found, instead of going down, on reaching North Point they went up the bay, in a north-easterly direction I deemed this knowledge of the utmost importance. My determination to run away was again revived.”

The Chesapeake played a major role in Douglass’s ability to find a way to escape:

“My sufferings on this plantation seem now like a dream rather than a stern reality.

Our house stood within a few rods of the Chesapeake Bay, whose broad bosom was ever white with sails from every quarter of the habitable globe. Those beautiful vessels, robed in purest white, so delightful to the eye of freemen, were to me so many shrouded ghosts, to terrify and torment me with thoughts of my wretched condition. I have often, in the deep stillness of a summer’s Sabbath, stood all alone upon the lofty banks of that noble bay, and traced, with saddened heart and tearful eye, the countless number of sails moving off to the mighty ocean. The sight of these always affected me powerfully. My thoughts would compel utterance; and there, with no audience but the Almighty, I would pour out my soul’s complaint, in my rude way, with an apostrophe to the moving multitude of ships:—

“You are loosed from your moorings, and are free; I am fast in my chains, and am a slave! You move merrily before the gentle gale, and I sadly before the bloody whip! You are freedom’s swift-winged angels, that fly round the world; I am confined in bands of iron! O that I were free! O, that I were on one of your gallant decks, and under your protecting wing! Alas! betwixt me and you, the turbid waters roll. Go on, go on. O that I could also go! Could I but swim! If I could fly! O, why was I born a man, of whom to make a brute! The glad ship is gone; she hides in the dim distance. I am left in the hottest hell of unending slavery. O God, save me! God, deliver me!”

The Chesapeake gave a glimmer of hope:

It cannot be that I shall live and die a slave. I will take to the water. This very bay shall yet bear me into freedom.

While freedom did not come immediately from the waters of the Chesapeake his drive to be free was not only rekindled but manifested in his eventual declaration to no longer lose his freewill, what little he had of it.  Through a series of violent interactions and a thwarted escape, Douglas found himself back in Baltimore. This time working in ship yards and learning about boats.

While he worked in the boatyard and learned a trade, it was this experience that fortified his intention to freedom.  For he was still a slave and not a freeman no matter how much he was enjoying his time in Fell’s Point.

“I was now getting, as I have said, one dollar and fifty cents per day. I contracted for it; I earned it; it was paid to me; it was rightfully my own; yet, upon each returning Saturday night, I was compelled to deliver every cent of that money to Master Hugh And why? Not because he earned it,—not because he had any hand in earning it,—not because I owed it to him,—nor because he possessed the slightest shadow of a right to it; but solely because he had the power to compel me to give it up. The right of the grim-vis-aged pirate upon the high seas is exactly the same.”

Frederick Douglass’ life was intertwined with the water and his course toward freedom would be bound by it.  How work in the shipyard allowed him the cover to mask his intentions and it gave him the tools by which to assimilate in a new society.

On attempting to escape Douglass wrote:

It required no very vivid imagination to depict the most frightful scenes through which I should have to pass, in case I failed. The wretchedness of slavery, and the blessedness of freedom, were perpetually before me. It was life and death with me. But I remained firm, and, according to my resolution, on the third day of September, 1838, I left my chains, and succeeded in reaching New York without the slightest, interruption of any kind. 

Frederick Douglass Marker

On finding freedom:

I have been frequently asked how I felt when I found myself in a free State. I have never been able to answer the question with any satisfaction to myself. It was a moment of the highest excitement I ever experienced. I support I felt as one may imagine the unarmed mariner to feel when he is rescued by a friendly man-of-war from the pursuit of a pirate.

As is often the case throughout Frederick Douglass’ autobiography the seagoing metaphors appear.

 “My free life began on the third of September, 1838. On the morning of the fourth of that month, after an anxious and most perilous but safe journey, I found myself in the big city of New York,  a free man – one more added to the mighty throng which, like the confused waves of the troubled sea, surged to and fro between the lofty walls of Broadway,”

Sailing may have saved Frederick Douglass and he describes his path to freedom in The Life and Times of Frederick Douglass :

“I had one friend—a sailor—who owned a sailor’s protection, which answered somewhat the purpose of free papers—describing his person, and certifying to the fact that he was a free American sailor. The instrument had at its head the American eagle, which gave it the appearance at once of an authorized document. This protection did not, when in my hands, describe its bearer very accurately. Indeed, it called for a man much darker than myself, and close examination of it would have caused my arrest at the start. In order to avoid this fatal scrutiny on the part of the railroad official, I had arranged with Isaac Rolls, a hackman, to bring my baggage to the train just on the moment of its starting, and I jumped upon the car myself when the train was already in motion. Had I gone into the station and offered to purchase a ticket, I should have been instantly and carefully examined, and undoubtedly arrested. In choosing this plan upon which to act, I considered the jostle of the train, and the natural haste of the conductor, in a train crowded with passengers, and relied upon my skill and address in playing the sailor as described in my protection, to do the rest. One element in my favour, was the kind feeling which prevailed in Baltimore and other seaports at the time, towards “those who go down to the sea in ships.” “Free trade and sailors’ rights” expressed the sentiment of the country just then.

In my clothing, I was rigged out in sailor style. I had on a red shirt and a tarpaulin hat and black cravat, tied in sailor fashion, carelessly and loosely about my neck. My knowledge of ships and sailor’s talk came much to my assistance, for I knew a ship from stem to stern, and from keelson to cross-trees, and could talk sailor like an “old salt.”

On sped the train, and I was well on the way to Havre de Grace before the conductor came into the negro car to collect tickets and examine the papers of his black passengers. This was a critical moment in the drama. My whole future depended upon the decision of this conductor. Agitated I was while this ceremony was proceeding, but still externally, at least, I was apparently calm and self-possessed. He went on with his duty—examining several coloured passengers before reaching me. He was somewhat harsh in tone, and peremptory in manner until he reached me, when, strangely enough, and to my surprise and relief, his whole manner changed. 

Seeing that I did not readily produce my free papers, as the other coloured persons in the car had done, he said to me, in a friendly contrast with that observed towards the others: “I suppose you have your free papers?” To which I answered: “No, sir; I never carry my free papers to sea with me.” “But you have something to show that you are a free man, have you not?” “Yes, sir,” I answered; “I have a paper with the American eagle on it, and that will carry me round the world.” With this I drew from my deep sailor’s pocket my seaman’s protection, as before described. The merest glance at the paper satisfied him, and he took my fare and went on about his business. This moment of time was one of the most anxious I ever experienced. Had the conductor looked closely at the paper, he could not have failed to discover that it called for a very different looking person from myself, and in that case, it would have been his duty to arrest me on that instant, and send me back to Baltimore from the first station. When he left me with the assurance that I was all right, though much relieved, I realised that I was still in great danger. I was still in Maryland, and subject to arrest at any moment. I saw on the train several persons who would have known me in any other clothes, and I feared they might recognise me, even in my sailor “rig,” and report me to the conductor, who would then subject me to a closer examination, which I knew well would be fatal to me.

Perhaps the most compelling part of this story of freedom and perseverance is the role sailing plays in it. We often forget that those enslaved people that reached the shore of America came here in sailboats.  Great ships in Africa that transported so many people across the Atlantic were in fact driven by the wind. 

The history of the United States is fundamentally rooted in the people that shaped its past, present, and future. In this case, the stories of Frederick Douglass and his relationship to the Chesapeake Bay Region are too often lost in the end product of his work in civil rights.  

Was Frederick Douglass a sailor? 

Sailing helped Frederick Douglass find freedom as it so often helps others find a new life. The difference though is paramount. Frederick Douglass was sailing to save his life.

Notes and Resources:

Narrative of the Life of Frederick Douglass, 1845

The Life and Times of Frederick Douglass, 1881

Frederick Douglass Timeline