Frederick Douglass led a full and productive life as an abolitionist, presidential advisor, activist, and orator. However, in the 21st century, we most remember him for his skills as a memoirist. Douglass’ autobiography, Narrative of the Life of Frederick Douglass, an American Slave, was a sensation upon its publication in 1845 and even now remains one of the most compelling chronicles of life under slavery in the United States. In it, Douglass describes the brutal reality of his life as a slave in Maryland, his efforts to educate himself, and ultimately, his resolve to escape to freedom.

Ironically, although it is the pivotal event of the Narrative, Douglass’ actual escape is entirely omitted from the published work; the Narrative is a book that leads to a climax that never arrives. Writing almost 20 years before the Emancipation Proclamation abolished slavery in America, Douglass was unable to describe his flight from Baltimore for fear that revealing his method or those who assisted him would hinder the escape of other slaves.

It wasn’t until 40 years later, in his third and final autobiography, The Life and Times of Frederick Douglass: From 1817–1882, that Douglass at last felt free to tell of his escape. To some degree, the account lacks the drama of other slave narratives that tell of closer brushes with capture, but with his usual eloquence, Douglass conveys the dread, fear, and anxiety that made his successful attempt so harrowing. It was a short episode in an inspiring life story, but it would be the most decisive event of his life.

Born into Captivity

Frederick Douglass was born Frederick Bailey and raised without mother or father on a Maryland plantation. Early in life, he witnessed the horrific treatment of his fellow slaves, many of whom were his own relatives. Rare instances of kindness fostered in him a hunger for knowledge as strong as the actual hunger he often experienced as an underfed, overworked farm hand.

Fortunate enough to be loaned out to another family in Baltimore when he was still a child, he spent his formative years in a city household far less cruel than that of the plantation. It was there that he covertly learned to read and write and to fashion his first notions of escaping a system he now recognized as inherently corrupt and unfair.

When both master and mistress in Baltimore died, Douglass was returned to the plantation, a setting for which he was now poorly equipped. The plantation was now owned by Thomas Auld, the son-in-law of the landowner who had originally purchased Douglass. Auld was a cruel man who treated his slaves poorly, and he immediately viewed Douglass as a liability. Douglass was beaten for minor infractions and eventually lent out for a year to a farmer known for “breaking” slaves.

The farmer’s reputation was well deserved. After six months of constant beatings, Douglass indeed felt broken. Finally, following one particularly brutal and bloody incident, Douglass had had enough – he grabbed the farmer by the throat and threatened to kill him if he touched him again. Although he could very easily have been lynched for the act, instead the farmer left him unpunished for fear of damaging his reputation as a “negro breaker.” Douglass calmly worked out the remainder of his year unmolested, and he found himself strengthened by his defiance. Loaned out soon afterwards to another landowner (named “Freeland,” of all names), he became more determined than ever to escape.

First Attempt

An opportunity for escape presented itself during the Easter holidays of 1835, when Douglass and a group that he secretly assembled planned to borrow a canoe and paddle up the Chesapeake to freedom. The plan came to nothing when a member of the group betrayed the others, and they were arrested. However, there was no actual evidence to prove that the men had planned an escape (Douglass and his cohorts disposed of the papers he had forged by eating or burning them), and so Douglass was returned to the plantation after a short and inconclusive jail stay.

Now known in the region as a troublemaker, Douglass had to be sent away or else be killed by overzealous whites. To prevent any loss on his investment, Auld sent Douglass back to Baltimore, to his owner’s brother, who found him work in the shipyards. Proving himself a talented caulker, Douglass for a time thrived at the work and became an apprentice to a ship-builder until anti-black sentiment drove him from the job. Douglass found other work, and soon he was trusted to find his own contracts and earn his own money. This allowed him a certain amount of free movement, but at the end of the week, of course, everything he earned would have to be turned over to his master. The injustice of this arrangement began to weigh heavily on Douglass’ mind and he knew he would have to try again to escape, even if it meant death. He began to put aside whatever money he could gather in preparation for the attempt.

The Final Escape

It is not a fact well known that in many Southern slave states, a slave’s freedom could be purchased. That is, a slave could be free if a certain amount of money was paid to the slave’s owner. Of course, virtually no slaves had money to purchase their own freedom, so becoming free usually meant having an owner who was kind enough to release his slaves and obtain “free papers” for them. These papers would allow a legally free black person to move about unimpeded.

A common tactic for escaping slavery depended on this system of free papers. A free black person could share his papers with a slave who roughly fit the papers’ description and hope that his papers allowed the slave safe passage to the north. It often worked, but the plan required knowing someone willing to part with his own papers for another person’s benefit. Should the owner of free papers be found without them, or caught passing them to someone else, it could mean jail or even the revoking of the papers and a return to slavery.

Frederick Douglass knew a man who was willing to take a chance on him. Down at the shipbuilding yards, he met a sailor who entrusted his special “sailor’s protection” papers to him. While not free papers exactly, the documents looked very official, with a large American eagle emblazoned on the top. Douglass hoped that they would serve as well as the real thing.

On Monday, September 3, Douglass left for work as usual. He changed into borrowed sailor’s clothes and waited until the last second to board the train going north out of Baltimore. Had he tried to buy an advance ticket, his ruse may have been discovered, but once on the train, he had only to pass the conductor’s eye. At that time and in that part of the country, sailors, even black sailors, were treated much the way we regard veterans now, as heroes doing honorable work for the country, so the conductor barely glanced at Douglass’ papers before selling him a ticket. Douglass had cleared the first and worst hurdle.

The trip north involved several transfers, from train to boat and from boat to train, and there were other close calls. While passing by ferry over the Susquehanna River in Delaware (also a slave state), an inquisitive black deck-hand made Douglass uncomfortable by asking too many questions, and Douglass got away from him as quickly as possible. Once aboard the next train, Douglass spotted one of his employers from the Maryland shipyards in the window of a Southern bound train that had stopped on the tracks opposite his train. Had the ship’s captain spotted him, Douglass would have been caught, but fortunately Douglass had spotted him first and evaded his view.

On his own train, Douglass was scrutinized closely by a man whom he recognized as a blacksmith from the shipyards. He was sure that the blacksmith knew who he was, but for whatever reason, the blacksmith did not betray him.

Finally, Douglass left the train and boarded a steamship at Wilmington en route to Philadelphia. Terrified that he would be arrested at this checkpoint, once again his credentials were not closely regarded and he passed through. Arriving safely in Philadelphia in the afternoon, Douglass took the train to New York, where he arrived on Tuesday morning. After 20 years in captivity, Douglass had made the leap to freedom in 24 hours.

A Free Man

Even after he made his escape, Douglass had to be careful. Unscrupulous people, both white and black, made a living by turning in escaped slaves to their owners. Fortunately, he stepped into the circle of the abolitionist movement gaining traction in New York. A helpful abolitionist secured him a place in New Bedford, Massachusetts. While working any job he could find, Douglass was prevailed upon to talk about his experiences at abolitionist meetings. At first, he found it difficult to speak about the life he had so recently left behind, but eventually he realized just how important his contribution to the cause could be.

Encouraged and promoted by leading abolitionist William Lloyd Garrison, Douglass was soon one of the major figures of the movement. He wrote the Narrative in response to public demand. The response to the book was so great that Douglass was in mortal danger after its publication. He was still an escaped slave, and a price was still on his head. For his own safety, he moved to England and lived there for two years. Douglass was so well received there, and so loved, that a collection was taken up to secure his freedom legally. Thomas Auld proposed a sum of £150 (roughly £13,000 now, or $20,000 in American currency). Douglass’ friends raised the money and had the joy of placing “free papers” in his hands at last. Douglass returned home to America in 1847 a free man.

Frederick Douglass’ eventful life was just beginning, and he would have many more experiences both uplifting and frightening along the way. He was an advisor to President Lincoln in the run-up to the Civil War, a recruiter for black soldiers during the Civil War, a politically appointed ambassador to the Dominican Republic after the war, a promoter of women’s suffrage after emancipation, and even the first African-American nominated for vice president on any party’s ticket. A man who had once been a household servant became one of America’s great public servants, and a brave bid for personal freedom had led to a lifetime devoted to seeking freedom for others.