Frederick Douglass, had received a very preliminary education and taught himself how to read and write. He was fueled with the desire for freedom from the oppressive masters he had surrounding him. He first tried to run away with Henry and John Harris in 1836. This escape attempt failed and Douglass was then sent to prison. His new master, William Freeland was a kind man, and life was much easier for him compared to his life with Edward Covey, who was strange and cruel master.

     He then went to Thomas Auld again, one of his old masters, and began to work in a shipyard in exchange for payment. Douglass began to save up money for a train ticket to Philadelphia. He borrowed a black sailor's papers as his proof that he was a free man. Douglass dressed as a sailor the best he could and jumped on board a train bound for Philadelphia. The conductor was fooled by his disguise and he safely reached the other side as a free man. He struggled to make money the first few days of his freedom in New York, but then he was able to work his way up by living with a free black family. He moved to Massachusetts, where he was completely free from Southern whites on the lookout for fugitive slaves.