Douglass introduces this chapter as a description of his successful escape. However, he says that he is unable to give a complete account of his flight, because disclosing all the facts of the escape would compromise those who helped him and make it more difficult for other slaves to escape.
This is one of the only sections of the novel where Douglass does not to attempt to fully recount the truth, and he only withholds this information because the truth would threaten people he cares about. In explicitly acknowledging that he is not giving the whole truth, he both frees himself from others charging him of not telling the full truth and also shows how slavery makes it impossible for slaves to be truthful about everything because to be truthful can lead to death.
Douglass also expresses his frustration with the very public way in which the underground railroad—a network of people who aid escaping slaves—operates. While he appreciates the bravery of those who run the underground railroad, he thinks their indiscretion makes it much more difficult for slaves to escape bondage. Douglass recommends keeping the slaveholder ignorant of the means by which slaves escape, so that the oppressors will torment themselves with all sorts of imaginary threats.
By proposing to keep the underground railroad secret, Douglass uses the slaveholders’ oppressive techniques against them: he seeks to keep slaveholders unenlightened to exploit their vulnerability, just as slaveholders try to keep their slaves as ignorant as possible.
In 1838, Douglass grew dissatisfied with forfeiting all of his earnings to Master Hugh. Sometimes, Hugh would let Douglass keep a tiny fraction of his pay, which only affirmed to Douglass that he had a right to keep all of it.
Douglass’s burgeoning knowledge of free life only makes his enslavement harder to bear—keeping some of his earnings only sharpens the pain of forfeiting the majority.
Master Thomas comes to Baltimore, and Douglass requests that he be allowed to work for pay. Thomas refuses this request, and tells Douglass to be complacent and obedient, and not to overthink his role. Douglass is not deterred, and soon asks Master Hugh for the privilege of finding his own freelance work and keeping some of his earnings. Hugh grants Douglass this ability, but demands that Douglass pay him three dollars per week off the top of his earnings. This arrangement is very good for Hugh: Douglass has to pay for his own room and board, while still paying money to his Master. However, Douglass accepts his new responsibilities as a step towards freedom.
Getting to keep most of his earnings is a dramatic step towards freedom for Douglass. Douglass’s willingness to accept this undoubtedly more difficult arrangement shows his determination to emancipate himself.
After a few months of this arrangement, Douglass neglects to pay Hugh his weekly tribute on time because he has gone to spend time with friends outside Baltimore. Hugh thinks Douglass is planning an escape and retracts the permission he gave Douglass to work on his own, and in retaliation, Douglass does no work for an entire week. When his next payment to Hugh is due, his master is furious, and the two men almost come to blows.
Douglass’s time working for his own earnings emboldens him to stand up in defiance of his master.
After this confrontation, Douglass decides to attempt an escape on the third of September. He works extremely diligently in the meantime, to dispel any of Hugh’s suspicions about an escape attempt.
Douglass keeps Hugh ignorant of his plans by acting as if he has no such plans. That Douglass can now keep his master ignorant shows that he now sees himself as the equal of his "master."
Douglass has mixed feelings about escaping, because he will be forced to part with the beloved friends he has made in Baltimore. His past failure also discourages him. However, he sticks to his resolution and successfully escapes.
That the simple, elemental desire to be free should force Douglass to give up his friendships is yet another indictment of slavery.
Douglass reaches New York City on September third, and initially feels great relief. However, this relief soon turns to further anxiety when he realizes that he still can be recaptured. He also experiences a crushing loneliness in the foreign city because he is unable to trust anyone.
Far from home and unable to trust anyone, Douglass can no longer enjoy the fellowship of his friends, and this deprivation takes a toll on his mental health.
Fortunately, Douglass is aided by a free black abolitionist and journalist, Mr. David Ruggles, who takes the fugitive slave into his boarding house and instructs him to go work as a caulker in New Bedford. While Douglass is in New York, he writes to and is joined by his fiancée, a free black woman named Anna Murray, whom he marries at a ceremony attended by Ruggles and conducted by the Reverend J.W. Pennington.
Finally, Douglass is treated like a human being. His marriage to Anna leaves him able to enjoy human fellowship at a level greater than he ever could while enslaved. Ruggles is the beginning of Douglass's move to become an activist against slavery—the educated black free men feel a duty of fellowship to the slaves left behind.
Douglass and his new wife board a steamboat for Newport, Rhode Island. Despite having no money to pay for transportation to New Bedford, they board a stagecoach and arrive at the house of Mr. Nathan Johnson, who treats them well and pays for their coach fare.
The altruism that Douglass encounters on his journey to Massachusetts paints a picture of the free north as generous and fraternal, and implies that this spirit may come from the area’s rejection of slavery.
Douglass begins to feel safe with Johnson. Douglass realizes that the name he had picked for himself, “Frederick Johnson,” is too common. Because “Frederick” is a large part of his identity, Douglass lets Johnson pick a new surname for him; Douglass now officially changes his name to “Frederick Douglass.”
Douglass’s transition into status as a full human is completed by his abandonment of his slave name. Taking on a new name is like a kind of baptism, a gaining of a new free self, untainted by slavery.
The comfort and splendor of life in New Bedford astounds Douglass, because he didn’t think such prosperity would have been possible without owning slaves. He had mistakenly assumed that all non-slaveholders would be as poor as the southerners who couldn’t afford slaves. Douglass is amazed that New Bedford lacks the destitution that some experience in the south, and is especially impressed that many free blacks in the north live more comfortably than some slaveholders in the south.
As his worldview expands, Douglass’s ignorance shrinks, and he loses the last of the misconceptions forced on him by enslavement—namely, the misconception that prosperity cannot exist without slavery. In fact, he comes to see the utter pointlessness of slavery—not only is it cruel and anti-Christian, but it produces a society that is less well off than the non-slaveholding north.?
On his third day in town, Douglass finds work loading oil onto a ship. He is unable to make use of his artisanal skills, because blacks are forbidden from doing caulking work in New Bedford, but he is nonetheless pleased to be working.
The racist laws that inhibit Douglass show that the free north is by no means perfect; however, Douglass is as optimistic and industrious as ever.
After a few months spent in New Bedford, Douglass begins to read the Liberator, the abolitionist newspaper run by William Lloyd Garrison. Douglass becomes dedicated to the abolitionist cause, and ends up speaking at an anti-slavery convention in August of 1841. He speaks little, because he is nervous of addressing white people, but he realizes that he has articulated himself well. With this small speech, Douglass began his role as an anti-slavery speaker and advocate, and dedicated himself to that cause.