Frederick Douglass, who became a leading statesman and abolitionist of unsurpassed eloquence, was born into slavery on Maryland’s Eastern Shore. (As was the case with many other slaves, Douglass grew up not knowing the exact date of his birth; ultimately, however, he chose February 14 as the date for celebrating his birthday each year.) By the time he was 20, the determined young man — he was first known as Frederick Augustus Washington Bailey but renamed himself Frederick Douglass after achieving his freedom – had made two unsuccessful efforts to escape the shackles of slavery. In 1838, Douglass made a third escape attempt. This one proved to be successful due to his strategic and effective use of a couple of modes of transportation while making his way from the slave state of Maryland to north of the Mason-Dixon line.
For this escape attempt, Douglass received pivotal assistance from a free African-American woman in Baltimore whom he had met and fallen in love with the previous year. Her name was Anna Murray, and she helped cover the travel expenses and other costs for Douglass’s escape attempt by borrowing from her savings and selling one of her beds. She also supplied him with other resources for his daring journey out of slavery.
Douglass’s escape attempt this time around started in earnest in Baltimore on September 3, 1838, when he managed to board a train of the Philadelphia, Wilmington and Baltimore Railroad (PW&B). Douglass took the train to the town (now city) of Havre de Grace, located in northeastern Maryland and along the southwestern shore of the Susquehanna River.
While Douglass was now only about 20 miles (32.2 kilometers) from the free state of Pennsylvania, the safer route for him to take was actually in the direction of the slave state of Delaware. He, therefore, boarded a PW&B steamboat ferry sailing from Havre de Grace to the Maryland town of Perryville on the other side of the Susquehanna River. For this part of his escape route, Douglass wore a sailor’s uniform that Murray had given him and carried the identification and protection papers of a retired African-American merchant sailor.
After reaching Perryville, Douglass boarded a PW&B train and traveled to the port city of Wilmington, Delaware. He then sailed on the Delaware River via steamboat to reach the free city of Philadelphia. From Philadelphia, Douglass took a train further up north. He arrived in New York City early on the morning of September 4. His high-risk trek was now complete, and his life’s mission to secure the freedom and rights of others had just begun.
“A new world had opened upon me,” Douglass later wrote when recalling his arrival in New York City. “It was a time of joyous excitement, which words can but tamely describe.” Murray soon joined him in New York City. Just 11 days after he had made it to the city, they were married. They remained together until her death in 1882. Frederick Douglass died 13 years later at the age of 77.
For more information on Frederick Douglass, including his 1838 escape from slavery, please check out https://en.wikipedia.org/wiki/Frederick_Douglass and https://www.loc.gov/collections/frederick-douglass-papers/articles-and-essays/.
Additional information on his escape is available at https://en.wikipedia.org/wiki/Philadelphia,_Wilmington_and_Baltimore_Railroad.
Transportation History 
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