- Douglass begins this chapter by letting us know that the part of the story we've been waiting for has finally come: escape from slavery!
- But even though he knows we've been waiting for this, he can't give us all the details. Remember, when this book was published, slavery was still legal, and the Underground Railroad, the organized effort to help slaves escape north, was still working in secret.
- Since Douglass can't give us the details of his escape without revealing to the slaveholders how it was done, he decides not to tell us anything at all. So if you were waiting for an exciting story of a thrilling escape, don't hold your breath.
- In later autobiographies, Douglass would tell the whole story: he disguised himself in the uniform of a sailor and used identification papers given to him by a freed black sailor to take a train to New York. In this book, though, Douglass just tells us the date it happened: on September 3, he escaped to freedom in New York.
- We expect Douglass to be really excited to be free. And at first, he is. But then reality sets in: he's in a strange place, he doesn't know anyone, and virtually anyone he meets could turn out to be an enemy trying to return him to captivity.
- Freedom, in other words, is complicated.
- A man named Mr. Ruggles helps Douglass find a place to stay, and together they plot his next move. The first thing he does is get married! He hasn't mentioned it until now, but he'd been planning to marry a free slave named Anna.
- Ruggles helps him write to her, telling her to come to New York, and then they find a church that will make them man and wife.
- After getting married, Douglass decides that New York is still too close to the South for his comfort. So he and his wife move to New Bedford, Massachusetts, where he hopes to get a job working as a caulker.
- Once again, Douglass has to depend on the kindness of strangers to help him. He keeps meeting people who loan him money to help him get on his feet. Douglass is trying hard to show us that it isn't enough to simply abolish slavery. Once slaves are freed, they need help creating new lives and livelihoods for themselves.
- Douglass is surprised to find that people in Massachusetts seem to be pretty well-off. He expected them to be poorer than in the South, since they don't have slaves working for free. It seems that here, where people work for themselves instead of being forced to work, the shipyards run cleanly and smoothly.
- When Douglass finally gets a job, he takes to his labor eagerly. For the first time, he is his own master. Even though he can't get a job as a caulker, he doesn't mind – he's working for himself!
- Not long after he arrives, Douglass subscribes to The Liberator, an abolitionist magazine, and slowly starts getting involved with the cause.
- In the last lines of the book, Douglass tells us a little about the anti-slaving convention that Garrison talked about in the preface. When the abolitionists asked him to speak, he says that at first he was shy.
- But it wasn't just embarrassment, the way Garrison portrayed it. Inside, he tells us, he still felt like a slave, and he didn't have the courage to speak in front of all those white people. When he finally does get up the courage, it represents his final transformation from a slave to a free man.