As the date of escape draws closer, Douglass experiences anxiety about leaving his many Baltimore friends and about the possibility of failure. Nonetheless, he carries his plan through and reaches New York City smoothly on the third of September. Rather than feeling relieved upon reaching New York, however, Douglass is seized with terror. He finds himself in an unfamiliar city, without shelter, food, money, or friends. He is surrounded by people, but afraid to speak with anyone for fear they will turn him in. Soon, though, a free black named David Ruggles takes Douglass in. Ruggles, an abolitionist and journalist, advises Douglass to go to New Bedford, Massachusetts, to find work as a caulker. Douglass writes to his fiancée, Anna Murray, a free black woman from Baltimore. Anna joins Douglass in New York. Ruggles witnesses their marriage and gives Douglass five dollars and a letter of recommendation.
When Douglass and Anna reach New Bedford, they receive help from Mr. and Mrs. Nathan Johnson, who pay their travel debt and help Douglass choose a new name. Mr. Johnson suggests “Douglass,” the name of a knight in Sir Walter Scott’s Lady of the Lake.