Literacy and a growing social consciousness made Frederick into an unruly bondsman. In 1833, after being taken by master Thomas Auld to a plantation near St. Michael's, Maryland, he organized a secret school for slaves, but it was discovered and broken up by a mob of local whites. To discipline Frederick, Auld hired him out to a local farmer who had a reputation as a "slave breaker." Instead he became increasingly defiant and refused to allow himself to be whipped. Hired out to another local farmer, he again organized a secret school for slaves. Before long, he and his pupils had plotted to escape to the free state of Pennsylvania, but this too was discovered. Expecting further trouble from Frederick, Auld returned him to Baltimore in 1836 and hired him out to a local shipyard to learn the caulking trade. Taking advantage of the relative liberty afforded by the city, Frederick joined a self-improvement society of free black caulkers that regularly debated the major social and intellectual questions of the day.
After an unsuccessful attempt to buy his freedom, Frederick escaped from slavery in September 1838. Dressed as a sailor and carrying the free papers of a black seaman he had met on the streets of Baltimore, he traveled by train and steamboat to New York. There he married Anna Murray, a free black domestic servant from Baltimore who had encouraged his escape...he adopted the surname Douglass to disguise his background and confuse slave catchers.