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Douglass first tried to escape from Freeland, who had hired him out from his owner Colonel Lloyd, but was unsuccessful. In 1836, he tried to escape from his new owner Covey, but failed again. In 1837, Douglass met and fell in love with Anna Murray, a free black woman in Baltimore about five years older than he was. Her freedom strengthened his belief in the possibility of gaining his own freedom. On September 3, 1838, Douglass successfully escaped by boarding a train to Havre de Grace, Maryland. Dressed in a sailor's uniform, provided to him by Murray, who also gave him part of her savings to cover his travel costs, he carried identification papers which he had obtained from a free black seaman. He crossed the Susquehanna River by ferry at Havre de Grace, then continued by train to Wilmington, Delaware. From there he went by steamboat to Quaker City (Philadelphia, Pennsylvania), and continued to the safe house of abolitionist David Ruggles in New York; the whole journey took less than 24 hours. Frederick Douglass later wrote of his arrival in New York: 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. Anna Murray-Douglass, Douglass' wife for 44 years Once Douglass had arrived, he sent for Murray to follow him to New York; she arrived with the necessary basics for them to set up a home. They were married on September 15, 1838, by a black Presbyterian minister eleven days after his arrival in New York. At first, they adopted Johnson as their married name.

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Frederick Douglass (born Frederick Augustus Washington Bailey, c. February 1818 - February 20, 1895) was an American social reformer, orator, writer and statesman. After escaping from slavery, he became a leader of the abolitionist movement, gaining note for his dazzling oratory and incisive antislavery writing. He stood as a living counter-example to slaveholders' arguments that slaves did not have the intellectual capacity to function as independent American citizens. Many Northerners also found it hard to believe that such a great orator had been a slave. Douglass wrote several autobiographies, eloquently describing his experiences in slavery in his 1845 autobiography, Narrative of the Life of Frederick Douglass, an American Slave, which became influential in its support for abolition. He wrote two more autobiographies, with his last, Life and Times of Frederick Douglass, published in 1881 and covering events through and after the Civil War. After the Civil War, Douglass remained active in the United States' struggle to reach its potential as a land of the free. Douglass actively supported women's suffrage. Without his approval, he became the first African American nominated for Vice President of the United States as the running mate of Victoria Woodhull on the impracticable and small Equal Rights Party ticket. Douglass held multiple public offices. Douglass was a firm believer in the equality of all people, whether black, female, Native American, or recent immigrant, famously quoted as saying, I would unite with anybody to do right and with nobody to do wrong.

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