Douglass learns the alphabet and how to spell small words from this woman, but her husband, Mr.Auld, disapproves, and states that if slaves could read, they would not be fit to be slaves, being unmanageable and sad. Auld disapproves of slaves being taught how to read, Douglass realizes the importance of reading and the possibilities that this skill could help him.
After a two-hour long physical battle, Douglass ultimately conquers Covey. Douglass is not punished by the law, which is believed to be due to the fact that Covey cherishes his reputation as a "negro-breaker", which would be jeopardized if others knew what happened.
When his one-year contract ends under Covey, Douglass is sent to live on William Freeman's plantation.
Woefully beaten, Douglass goes to Master Hugh, who is kind regarding this situation and refuses to let Douglass return to the shipyard.
Master Hugh tries to find a lawyer but all refuse, saying they can only do something for a white person.
He is then moved through a few more situations before he is sent to St. His regret at not having attempted to run away is evident, but on his voyage he makes a mental note that he traveled in the North-Easterly direction and considers this information to be of extreme importance. He is harshly whipped almost on a weekly basis, apparently due to his awkwardness.
For some time, he lives with Master Thomas Auld who is particularly cruel, even after attending a Methodist camp. He is worked and beaten to exhaustion, which finally causes him to collapse one day while working in the fields.
Douglass eventually finds his own job and plans the date in which he will escape to the North.
He succeeds in reaching New Bedford, but does not give details of how he does so in order to protect those who helped him and to allow the possibility for other slaves escape by similar means.
Douglass comments on the abuse suffered under Covey, a religious man, and the relative peace under the more favorable, but more secular, Freeman.
On Freeman's plantation, Douglass befriends other slaves and teaches them how to read.
Douglass and a small group of slaves make a plan to escape, but before doing so, they are caught and Douglass is put in jail.