Douglass looked back on September 3, 1838 as the day when his “free life began,” but he encountered several close calls during his journey to freedom.
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Published: September 03, 2013 Last Updated: May 27, 2025
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.
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.
Illustrations depicting Frederick Douglass’s life from slavery to abolitionist.
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