A year passes. Sal finishes his novel and attends school on the GI Bill. Through writing to Dean in San Francisco, Sal learns that Dean is coming back East. In Testament, Virginia, while Sal and his aunt are visiting Southern relatives for Christmas, a '49 Hudson pulls up carrying Dean, Marylou, and Ed Dunkel. Sal is surprised and happy to see his friend. Dean soon volunteers to haul furniture for the family back to New Jersey.
Sal learns that Dean was living in San Francisco with Camille for the year. He and Ed Dunkel were working on the railroad, and when Dean saw the Hudson for sale he spent all his savings on it. Ed married a girl in San Francisco just so she would pay for the trip East, and thus they have headed to pick up Sal and return him to San Francisco. Ed's wife's money ran out by Tuscon, however, so the men left her in a motel and kept traveling, picking up various hitchhikers along the way to help pay for gas. Dean picked up Marylou, his former wife, in Denver. They decided that this time "they were going to stick." Through accidents and snowstorms the group made its way across the country and eventually to Sal's relatives' house in Virginia.
Sal, Dean, Ed, and Marylou head to downtown Testament to buy supplies for their trip. Dean is as compulsive and frenzied as ever. As the group returns to Sal's relatives' house, Sal realizes that he although he had been spending a quiet Christmas in the country, "the bug was on me again, and the bug's name was Dean Moriarty." They load Dean's car with furniture and begin to drive the thousand miles to New Jersey.
Sal tells the group about a girl he has been dating, Lucille, and talks about wanting to maybe get married and settle down. The group ends up eating free hamburgers in a diner after the owner asks them to wash the dishes. After driving through New York City, they head for Sal's aunt's house in New Jersey and sleep. In the morning, Sal gets a call from Ed's forgotten wife, Galatea. She had made it to New Orleans and was looking for Ed. Sal promises they will pick her up on their way back to San Francisco. The group meets up with Carlo Marx, who "quieted down" since the Denver days and now relates stories of a trip he took to Africa. After a quick meal of rice, Dean and Sal drive back to Virginia to pick up Sal's aunt and the rest of the furniture.
During the overnight drive to Virginia, Sal and Dean talk about the existence of God, his reformed behavior from his youth, and about how Dean was now a mystic. On the trip back to New Jersey, with Sal's aunt in the car, they get pulled over by a Washington police officer. With no money to pay the speeding fine, Sal's aunt has to pay. Sal's aunt believes that the world will never find peace until "men fell at their women's feet and asked for forgiveness." This exclamation causes Dean and Sal to reflect on how they do not understand the women in their lives. They arrive in New Jersey, where Sal's aunt cooks a meal for everybody.
Sal, Dean, and Ed head into New York to find a place to live for a while. While driving in, Sal becomes haunted by the idea that he forgot something-a decision he was supposed to make before Dean arrived. The decision had to do with the Shrouded Traveler, a figure in a dream whom Sal decides represents death. Dean thinks the Shrouded Traveler represents a "pure death," the state of bliss experienced first in the womb and not again until a person dies. Dean decides he will have nothing to do with this kind of death, and Sal agrees with him.
They begin to visit friends in New York for the New Year's weekend. They party for three days. Lucille, Sal's girlfriend, becomes distressed when she sees how crazy Dean makes Sal. Marylou, realizing that Dean is going back to Camille in San Francisco, tries to get Sal to be her man, but he refuses. Sal realizes his affair with Lucille cannot last much longer because she wants things "her way" and Sal is not ready to give up his life of traveling. The New Year's parties get bigger and bigger, and a cast of characters and New York friends come in and out, including Rollo Greb, a beatnik scholar who Dean believes "get(s) it." When Sal tries to find out what "it" is, Dean's only response is "IT! IT!"
During the weekend, Sal and Dean visit a jazz club to see a musician Dean says also has "it." The musician, a blind piano player named Shearing, enraptures Dean and Sal, partly because of his playing and partly because of the marijuana they are smoking. When Shearing is finished, Dean points to his empty chair and exclaims, "God's empty chair ...." Sal feels the madness of the weekend overcoming him.
After a rest at his aunt's house, Sal decides to go back West with Dean, partly to see what "Dean was going to do" and partly so that he can try to have an affair with Marylou once Dean goes back to Camille. The group spends a few more days in Carlo Marx's apartment where Carlo lectures them on what they are making of their lives; Carlo talks to them about his new role as "The Voice of Rock"-a new period of madness for Carlo. One night in a "hoodlum" bar, Dean proposes that Sal try to sleep with Marylou, just so that Dean can know what she is like with another man. They drive back to the apartment and wake Marylou. While Dean watches, Sal and Marylou try to make love, but Sal confesses he wants to wait until they get to San Francisco because his "heart isn't in it." Dean returns and makes love to Marylou, an act that Sal believes is Dean's attempt to realize the "origins of life-bliss," a need he developed from his neglectful parents and his time in prison.
The group call their friend Old Bull Lee in New Orleans, who has been taking care of Ed's abandoned wife, and they promise they are coming to get her. Sal tells his aunt goodbye and that he will be back in two weeks-and the group is off for California.
Back on the road, Sal realizes the group is "performing our one and noble function of the time, move." Dean encourages the others to forget their worries and fights of the past and to focus on the good time they will be having in New Orleans. Dean and Marylou make plans to sneak around behind Camille's back when they get to California, and Sal realizes he is not going to get to "make it" with Marylou after all.
They arrive in Washington, D.C., on the day of Harry Truman's second inauguration and watch a military parade go down Pennsylvania Avenue. They get pulled over again in Washington, and the cops try to put Dean and Marylou in jail under the Mann Act, a 1944 law that prohibits the transport of women for prostitution. The cops threaten them but end up only giving Dean a $25 fine. Sal accuses the police in America of being engaged in psychological warfare against its citizens, making up crimes and invading people's privacy.
In Virginia, they pick up a Jewish hitchhiker before they reach Testament. The hitchhiker says he will get the group some money, but he never shows back up, so they leave. The group drive through the South stealing gasoline and cigarettes. In Alabama Dean begins telling stories of his childhood. They arrive in New Orleans to the sound of jazz music on the radio. They take in the sights and smells of the South and of New Orleans and exclaim their love for women. They find Old Bull Lee's house outside of town. Ed and Galatea, his forgotten wife, are reunited. Bull Lee is a schizophrenic drug addict who held a myriad of odd jobs all over the world, but he is warm and cordial to the "maniacs" he finds when he comes home. Sal relates several old tales about Bull Lee: he had studied multiple disciplines all over the world and now wanders the streets of New Orleans with different shady characters feeding his Benzedrine habit.
Bull Lee takes the group into New Orleans, but they hit only the "dull bars in the French Quarter." They cross the Mississippi on a ferry, and a girl commits suicide on the boat. Back at Bull's house Marylou takes every drug that Bull will give her, and the rest of the group get high on marijuana. Sal tries to take a walk to the river but cannot reach it because of a fence. With a volume of Kafka on his lap, Bull Lee muses, "When you start separating the people from their rivers" what you get is "Bureaucracy!"
Part Two begins with Sal's rebirth from his family life to his life on the road once again as Ed, Dean, and Marylou arrive to take Sal back West. These first three chapters begin to explore the notion of male freedom within the structures of heterosexual family and marriage that defined this time period of the Forties and Fifties. Dean and Ed treat Ed's wife as disposable, leaving her in a hotel on the journey, and Dean leaves Camille, his love interest from earlier, to return to his wife Marylou. Dean comments that he truly does want real love, but he only wants it "free of hassles," meaning the freedom to come and go and do as he pleases. In On the Road women are portrayed as being able to provide food, shelter, sex, and warmth at their own cost and in exchange for both freedom and adventure for men. There is no sense of commitment in Dean's life, and Sal follows this lead by giving up his dreams of marriage and family with Lucille to follow Dean on the road. In Sal's eyes, Dean has transformed in a year from a merely excited individual to an ecstatic prophet. His thoughts and actions take on religious significance in Sal's eyes. Dean's presence interrupts the quiet family gathering in Virginia, and Dean, also likened by Sal to a virus, brings Sal back to the road.
Themes of matriarchal rule also come up in these chapters. After the speeding ticket, Sal's aunt is the one who takes control, paying the fine and returning home to cook and care for the young people. Just as Kerouac did in his real life, Sal is caught in the position of assigning roles to women-either of mothers or of sexual objects-making it unclear how he will achieve true love and marriage.
The reader gets a further glimpse into the racial fascination that Kerouac develops throughout the novel. Dean dances to a Bebop record that Sal has bought, and he idolizes an old black man riding a mule on a farm. Carlo took a trip to Africa, where he immersed himself in African culture. Kerouac suggests that black culture carries forward certain truths that white American culture has lost. As in Part One, when Sal idealized migrant farm life, the theme of race and its interplay with "It" plays an important role and will continue to do so.
With the return of Dean and the promise of another adventure out West, both Sal's life and Kerouac's narrative begin to increase in disorder. Kerouac's writing begins to take on a more frenzied nature, emblematic of the characters he is describing. His sentences often run into each other without punctuation, and he jumps from theme to theme, sometimes within the same paragraph or the same sentence. As with the writing, Sal's life becomes more frenzied and disordered. The sexual lives of Kerouac's characters become entangled with each other as Sal and Dean want to exchange lovers and Dean propositions Sal to sleep with Marylou while he watches.
Sal's philosophy of life also becomes darker and more disordered. He relates his vision of the Shrouded Traveler, a representative of death. Dean, having become more intense since the earlier chapters, assures Sal that one can reach a true understanding of life if one only moves fast enough. Kerouac suggests that his characters are trying to take on immortality by the very speed and pace of their lives as well as through their travels. Dean's motto for life and path to immortality is twofold: move and don't worry.
This quest for immortality and individuality is arrested, however, by the police and military presence the travelers encounter in Washington. As Bull Lee comments at the end of chapter six, this "bureaucracy" intrudes into people's lives and keeps them from expressing themselves and living life to its fullest. The group's reaction to these machines of war parading in Washington and the police that later pull them over shows just how removed they have become from mainstream American values.
Arriving in New Orleans, Sal and Dean are once again excited by the novelty of the African American culture in which they hope to participate. They meet up with Bull Lee, a character modeled after the legendary Beat poet William S. Burroughs, who models an eccentric, drug-addled lifestyle for the group. The stay at Bull Lee's only intensifies the disorder taking over on this trip out West. The Mississippi River makes another appearance in the novel as gateway to the West. Sal begins to create an American mythology out of the river as both a chance at new life, symbolized by his crossing of the great river, and as a peril of death, symbolized by the oft-used literary trope of the girl who commits suicide.