After Covey, Frederick was hired out to William Freeland and attempted an unsuccessful escape with five other slaves. Eventually he was returned to Baltimore, and Hugh Auld rented him out to work in the shipyards. On September 3, 1838, with the help of a freedwoman, Anna Murray (who later became his wife), he escaped to New York City, disguised as a free sailor. In the Narrative, Douglass is not forthcoming about his exact escape route. Slavery still existed, and he didn't want to prevent other slaves from escaping in a similar way.
In New York, Douglass soon discovered that living as a refugee and hiding from slave hunters was not easy, so he accepted help from abolitionists who provided shelter and passage to New Bedford, Massachusetts. It was then that he changed his last name to "Douglass" in order to take possession of his own life and fate. On arriving in New Bedford, Frederick and Anna lived with Nathan Johnson, and it was Johnson who suggested that Frederick change his name. "Bailey" was too dangerous and could lead to his capture. Johnson suggested "Douglass" because he admired the heroic Scottish hero of Sir Walter Scott's Lady of the Lake.
