Several years later, as a result of his original owner's death, Douglass finds himself being lent to a poor farmer with a reputation for "breaking" slaves. Douglass spends a year with Covey, who cruelly and brutally whips the slave until Douglass finally fights him. From that day on, Covey leaves Douglass alone.
Douglass lives for a time with William Freeland, a kind master, and Douglass finds a family among the other slaves there. Douglass becomes a Sunday school teacher to other slaves, a position he enjoys. Although this situation is better than any he has experienced, it is still a far cry from freedom, so Douglass attempts to escape by canoeing up the Chesapeake Bay. He is caught and eventually finds himself working again for Hugh Auld in Baltimore. First, he runs errands for shipyard workers, but he after some of the workers heckle and strike Douglass, he fights back and is nearly beaten to death. Working at a different shipyard after the fight, Douglass becomes proficient at ship caulking, but he is forced to turn his wages over to Auld. Douglass soon makes an arrangement with Auld to hire himself out and give Auld a set amount of wages each week. Douglass is allowed to pocket the rest, thus saving enough for his escape to New York.
After his escape, Douglass is advised to move to New Bedford, Massachusetts, and he settles there with his new wife, Anna Murray. Douglass makes a living doing odd jobs; he is unable to find work as a caulker, however, because the white caulkers refuse to work with blacks, fearing the former slaves will take over their jobs. Although he still fears being caught and returned to the South, Douglass attends an anti-slavery convention, where he is encouraged to speak. This forms the beginning of his life in the public eye, speaking and writing in favor of the abolition of slavery.
