(I call him "Frederick" throughout this post for he was shedding Bailey, would not take up Douglass for another week or two, and had perhaps not yet assumed the name "Johnson" that he used when he married Anna a few days later.)
Those three weeks had their moments of apprehension. He knew that he would be severing the ties that he had with the community he had formed in Baltimore that had helped him develop his mind and sense of self. "The love of them was my tender point," he admitted, "an shook my decision more than all things else." Furthermore, while he had failed in a previous escape attempt, he felt certain that a failure this time would doom him to slavery forever. "I could not hope to get off with any thing less than the severest punishment," he knew, "and being placed beyond the means of escape."
(Imagine, for a moment, an alternate history in which he was discovered, punished, and sold into a coffle to New Orleans. What mischief would he have wrought on the Mississippi? Would he have led a school? A revolt? A maroon community in the swamps? Would he have survived another Covey-like encounter? Would he have found a wife and had children and died an early death of overwork or stroke or heart attack from containing the rage to preserve their lives?)
He was not entirely alone, however. Anna planned to join him, and she was among those helping him prepare. She and their future life and children were also a reason to make this escape succeed. He protected her respectability just as he protected his Baltimore friends' identities by not mentioning them by name in the planning in his first two autobiographies lest the "underground railroad" become and "upperground" one.
Decades passed before he told the details of his escape, and you can find an account in the first chapter of the second part of his third autobiography, Life and Times of Frederick Douglass. He begins by telling of the dangers in telling the tale before the end of slavery, "for publication of details would certainly have put in peril the persons and property of those who assisted." The Fugitive Slave Law of 1850 was still in the country's future when he lit out for freedom in 1838, but aiding a fugitive was still a crime and federal law sided with slaveholders.
He told his audience that he would have shared his story much earlier "had there been anything very heroic or thrilling in the incidents connected with my escape." How to top Harriet Tubman's multiple missions to retrieve her family from Maryland, or the Crafts' ingenious disguise of master and "man servant" when they boarded a train in Savannah, or Henry "Box" Brown mailing himself north, or the "Jerry Rescue" in Syracuse? "My success was due to address rather than courage;" he demurred, "to good luck rather than bravery."
First, he borrowed a Seaman's Protection Certificate from a black sailor friend. who clearly trusted him to return it. (Mystic Seaport has a database of many.) After all, that sailor was vulnerable to kidnapping or arrest during the time that he did not have the papers upon him. Then, he purchased a ticket with the money that he had saved and the money donated by Anna Murray from the sale of a featherbed. Black hackman Isaac Rolls brought his baggage to the train station, timed to arrive just as the train departed. Frederick, dressed in a sailor's uniform sewn by Anna, grabbed his belongings and hopped on the train as it began moving. His life in a maritime community allowed him to fit into his role well-enough to evade detection, "for I knew a ship from stem to stern, and from keelson to cross-trees, and could talk sailor like an 'old salt.'" Even his cocky attitude toward the conductor asking to see his free papers suited the part.
The train sped through Maryland, and while fast for the time, not as quickly as Frederick would have liked. They crossed into Delaware, which he reminded his readers was still "another slave State, where slave catchers generally awaited their pray, for it was not in the interior of the State, but on its borders, that these human hounds were most vigilant and active." At Havre de Grace, he boarded a ferry, where a black boat hand hoped to trade sea stories and nearly blew his cover. The same nearly happened again after the crossing when, on his second train of the trip, he spied a white captain from Baltimore on the opposite platform and a blacksmith "whom I knew well" on the same train as himself. The blacksmith, Frederick was sure, recognized him, "but had no heart to betray me."
This second train took him to Wilmington, Delaware, where he transferred to a steamship. The steamship took him upriver to Philadelphia. In Philadelphia, he found his way to the Willow Street train station, and too his third train trip to New York. The whole business took place in the space of twenty-four hours.
When you drive I-95 or take Amtrak from Baltimore to New York City, you follow roughly the same path (but not exactly). I used to call it the Frederick Douglass Freedom Route when I lived down that way. At the end of this chapter he wrote that the end of this journey was "the end of my experience as a slave" and began the next chapter by declaring that "my free life began on the third of September, 1838. So, I like to call September 3rd "Frederick Douglass Freedom Day."
Frederick Douglass, Narrative of the Life of Frederick Douglass, ed. Blassingame, et al (1845; paperback, New Haven: Yale University Press, 2001).
Frederick Douglass, Life and Times of Frederick Douglass, ed. McKivigan, et al (1882; New Haven: Yale University Press, 2012).
Seaman Protection Certificates, and Register of Seaman Protection Certificates, G.W. Blunt White Library, Mystic Seaport.