Never had Frederick Douglass been so nervous. The butterflies in his stomach fluttered with every bounce of the carriage over Baltimore’s cobblestone streets as he approached the Baltimore and Ohio railroad station. The enslaved man, then known by his birth name of Frederick Augustus Washington Bailey, was embarking on a perilous journey with New York—and freedom—his intended destinations. 

After Douglass’ attempt to escape slavery two years prior was betrayed by a fellow enslaved person, he had been jailed, sent to Baltimore by his master and hired out to work in the city’s shipyards. Undeterred, Douglass vowed to try to escape again on September 3, 1838, although he knew the risk. “I felt assured that if I failed in this attempt, my case would be a hopeless one,” he wrote in his autobiography. “It would seal my fate as a slave forever.”

Douglass disguised himself as a free Black sailor, a creditable ruse given the nautical knowledge he gained from working on the waterfront. He also knew that the deference shown to sailors in a seafaring city such as Baltimore could work to his benefit. He donned a red shirt and sailor’s hat and loosely knotted a black cravat around his neck. Into his pocket, Douglass stuffed a sailor’s protection pass, which he could present in lieu of the “free papers” that railroad officials required Black passengers to carry as proof they were not enslaved. Douglass had borrowed the document from a free African American seaman, but he bore little resemblance to the physical description detailed on the piece of paper. Close examination by a railroad official or any authority would reveal the subterfuge and imperil both Douglass and his friend.

To avoid the scrutinizing eyes of the ticket agent inside the station, Douglass waited and jumped on the moving train at the last moment as it began to puff its way north. Many minutes passed before the conductor finally entered the segregated passenger car bearing the train’s African-American riders. Although Douglass remained calm on the outside, his heart pounded as the conductor carefully inspected the passengers’ free papers. “My whole future depended upon the decision of this conductor,” he wrote.

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Illustrations depicting Frederick Douglass’s life from slavery to abolitionist.

Finally, the railroad official came to Douglass’ seat. “I suppose you have your free papers?” he asked.

“No, sir; I never carry my free papers to sea with me,” the enslaved man said.

“But you have something to show that you are a free man, have you not?” the conductor queried.

“Yes sir, I have a paper with the American eagle on it, that will carry me round the world,” Douglass responded. Douglass pulled the document out of his pocket. The eyes of the conductor were drawn to the authoritative eagle emblazoned on the top rather than to the erroneous physical description. After a quick glance, the conductor collected Douglass’ fare and continued to the back of the rail car. “Had the conductor looked closely at the paper,” Douglass wrote, “he could not have failed to discover that it called for a very different looking person from myself.”

Douglass’ anxiety did not totally fade along with the conductor’s footsteps, however. He remained subject to arrest at any moment as the train passed through the slave states of Maryland and Delaware. The faster the train sped, the slower it seemed to drag to the fleeing Douglass. “Minutes were hours, and hours were days during this part of my flight,” he wrote.

In addition, Douglass’ cover was nearly blown on multiple occasions. The trip required him to cross the Susquehanna River by ferry, and on board was an old acquaintance who began to ask probing questions about his journey before Douglass could break away. Then, boarding a northbound train across the river, Douglass looked through the window of another train stopped on the track and spotted a white ship captain for whom he had recently worked. 

The captain’s gaze never fixed on Douglass, but the eyes of a German blacksmith whom Douglass knew did fall upon him. The blacksmith looked at Douglass intently but never called him out to the railroad officials. “I really believe he knew me,” Douglass wrote, “but had not heart to betray me.”

Frederick Douglass
Everett Collection
Frederick Douglass, circa 1847.

In spite of the obstacles, Douglass arrived safely in New York less than 24 hours after leaving Baltimore. Although on free soil, Douglass was not legally a free man. Packs of slave catchers roamed the streets of New York searching for fugitives. Anti-slavery activist David Ruggles sheltered Douglass until his intended wife, a free Black housekeeper named Anna Murray, arrived from Baltimore. 

The afternoon following their nuptials, Douglass and his new bride set off to safer refuge in New Bedford, Massachusetts. There, Douglass began his life as an abolitionist crusader. To better conceal his identity, he changed his last name from Bailey to Douglass. His supporters eventually raised enough money for Douglass to purchase his liberty and become a free man in the eyes of the law.

When Douglass published his autobiography in 1845, he divulged few details about his escape in order to protect those who abetted him and to keep authorities ignorant of the method he employed to slip the bonds of slavery. It was not until 1881 that he finally detailed his escape. 

Douglass always looked back on February 14, 1838, as the day when his “free life began,” and for the rest of his life he celebrated the date in place of his unknown birthday.