Douglass spent seven years in Baltimore before being sent back to Hugh Auld's brother, Thomas Auld, who hired him out to work as a slave for Edward Covey, a farmer notoriously dubbed the slave breaker. Douglass was whipped regularly and poorly fed during his time working for Covey. One day, after numerous beatings by Covey, Douglass fought back. Their confrontation lasted nearly two hours long and ended with Covey lost. He never tried to beat Douglass again. In 1836, Douglass tried to escape from Covey but was jailed after his plan was discovered.
[Edward Covey was a] first rate hand at breaking young negroes.
My Bondage and My Freedom by Frederick Douglass
In 1837, Douglass met and fell in love with Anna Murray, a free black woman in Baltimore. Murray's free status strengthened Douglass's determination to earn his own freedom. On September 3, 1838, Douglass successfully fled from Baltimore. His journey to freedom included:
- A train ride from Baltimore to Havre de Grace, Maryland
- A ferry ride across the Susquehanna River
- A train ride to Wilmington, Delaware
- A steamboat ride to Philadelphia, Pennsylvania
Dressed in a sailor's uniform provided to him by Murray and carrying identifications he obtained from a free black seaman, Douglass continued from Philadelphia to New York City to a safe house operated by abolitionist David Ruggles. His whole journey took less than 24 hours.
Murray followed him to New York and the two were married 11 days later on September 15. They settled in New Bedford, Massachusetts.
I have often been asked, how I felt when first I found myself on free soil. And my readers may share the same curiosity. There is scarcely anything in my experience about which I could not give a more satisfactory answer. A new world had opened upon me. If life is more than breath, and the 'quick round of blood,' I lived more in one day than in a year of my slave life. It was a time of joyous excitement which words can but tamely describe. In a letter written to a friend soon after reaching New York, I said: 'I felt as one might feel upon escape from a den of hungry lions.' Anguish and grief, like darkness and rain, may be depicted; but gladness and joy, like the rainbow, defy the skill of pen or pencil.
Life and Times of Frederick Douglass by Frederick Douglass