Douglass first unsuccessfully tried to escape from Freeland. In 1836, he tried to escape from his new owner Covey, but failed again.
On September 3, 1838, Douglass successfully escaped by boarding a train to Havre de Grace, Maryland. Dressed in a sailor's uniform, he carried identification papers provided by 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 New York; the whole journey took less than 24 hours.
Frederick Douglass later wrote of his arrival in New York City:
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.
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