Sal arrives in San Francisco, two weeks late, and meets up with his old friend from college, Remi Boncoeur. Remi and his girl, Lee Ann, live by the docks in a housing project called Mill City, supposedly the only place in America where blacks and whites voluntarily live in the same neighborhood. After spending several weeks with Remi in his shack, Sal decides he needs a job, so Remi gets him one as a guard in the shipyard barracks.
The other guards are former cops who sit around and tell stories of arrests they made and riots they put down in Alcatraz. One night, before a group of sailors are to ship off in the morning, Sal attempts to keep order in the noisy barracks. Instead of keeping order, however, he ends up getting drunk with sailors and raising the American flag upside down the next morning-an offense he is told he could go to jail for.
Most of his nights at the barracks are spent with Remi. They walk the halls, and Remi devises plans to steal money from the sailors who stay there. One night they accidentally sneak into the room of the barracks supervisor, a man they name Dostioffski (a name Remi creates from his mispronunciation of Dostoevsky), and almost get caught. They also sneak into the barracks cafeteria and eat ice cream and steal food. One night Remi steals an entire load of groceries for his house, claiming that President Truman mandated that "we must cut down on the cost of living."
Between day trips into the city to see the Banana King, an old man who sells bananas on the street, and jaunts to an old freighter ship in the bay, Sal spends nights in the city trying to find a girl. He dreams of robbing a jewelry store. He tries to scare the homosexual men who make advances on him in the bathrooms of bars.
Sal is becoming tired and lonely in San Francisco, and his relationship with Remi and Lee Ann starts to deteriorate. After a night of gambling away all of their money at a race track, Remi and Lee Ann have a huge fight and Remi decides to break off his relationship with Lee Ann and his friendship with Sal. He only asks that Lee Ann and Sal pretend that everything is normal when his stepfather comes to town in a week. Both agree. Instead of behaving, though, Sal runs into one of his old friends from Denver, Roland Major, and they both get drunk and ruin the night for Remi, ruining what is left of their friendship. Sal, feeling as if he has reached the end of the road in his trip, decides to head back East.
Sal hitches rides down to Bakersfield and eventually has to take a bus into Los Angeles, where he meets a young Chicano girl named Terry who is running from her abusive husband. They hit it off and both think they are in love. In Los Angeles, they get a hotel room and begin to get drunk. Sal mentions offhand that a friend of his in New York could show her where to get work. Terry, getting drunk, misinterprets this and accuses Sal of being a pimp and trying to turn her into a prostitute. They have a fight, and Sal kicks her out of the room. Instead, Terry realizes she might be mistaken and they end up making love and falling asleep together.
In LA, Sal and Terry decide they need to get jobs to earn money before leaving for New York. Sal sees LA as a "jungle" filled with varying characters: hipsters, beats, criminals, and cops. They attempt to get jobs all over LA and Hollywood, but no one will hire them. They eventually decide to hitchhike back to New York with the thirteen dollars they have left. After Terry borrows some clothes from a friend and Sal buys some bad marijuana in a bar, they attempt to catch a ride out of LA, but only cars full of high school kids go by, making fun of Sal and Terry as they pass.
The next day they set off to try to find work picking grapes but still have no luck. Instead, they hitchhike to Terry's brother's house. Terry's brother and his friend Ricky take Sal and Terry all around the California countryside, drinking and trying to sell manure to farmers. They eventually end up in Mexico-town and get a hotel room. Sal and Terry are down to their last two dollars. For the next few days Sal, Terry, Terry's brother, Terry's son, and Ricky spend all their time getting drunk in a tent Sal rented. When their money eventually runs out, Sal gets a job picking cotton.
Sal enjoys picking cotton, even though his fingers bleed and his back aches. He is not very good at the job, though Terry and Terry's son help him. Each day Sal earns a dollar and a half, which he uses to buy food for the family that he sees as becoming his own. Sal begins to settle down into domesticity in the migrant worker tents with Terry and Terry's son. The months go by, the weather begins to turn cold, and the money begins to run out. Terry takes her son and Sal to her family, and they take Terry back in. Sal wires fifty more dollars from his aunt and prepares to go back to New York. After spending a night in a farmer's barn, Sal hitches his way to LA and buys a bus ticket to Pittsburgh.
When Sal reaches Pittsburgh, he hitches rides to Harrisburg. He meets the Ghost of the Susquehanna, an old hobo trying to hitch rides to Canada. They walk together for several miles in the wrong direction before Sal gets a ride back to Harrisburg. Sal realizes after meeting the Ghost that the East holds just as much wilderness and mystery as the West. Hungry, Sal eventually gets a ride with a salesman who apparently believes in forced starvation as a health benefit. The man eventually relents and offers Sal some food and drives him all the way to New York.
Sal arrives in Times Square in New York, and he relishes the busyness of the city. He panhandles for a quarter to take the bus to his aunt's house in New Jersey. He has made it home just in time, before the cold of winter sets in. He begins to settle in to his former life of writing. His aunt tells him that Dean was at her house to stay a few nights just two days before, but Dean then set off for San Francisco, where his girl Camille has an apartment.
Sal's arrival in San Francisco is met with great promise. His stay in Mill City, a city that houses both blacks and whites equally, is a promise of a progressive culture for Sal, an equality among human beings that he could not find in other places. His friendship with Remi Boncoeur (a name that means "good heart" in French) is emblematic of the hospitality that he expects to find in the city. But Sal eventually finds San Francisco to be just as lonely and conflicted as places in his previous travels. Remi and Lee Ann have a tumultuous relationship that is compounded by Sal's desire for Lee Ann. This highlights the theme of the separation between men and women, a theme throughout the novel that the reader encounters early with Sal's bad sexual experience with Rita Bettencourt. In the end, it is Remi's and Lee Ann's relationship, with Sal's unwillingness to conform to the codes of hospitality when meeting Remi's father, that causes the friendship to break apart.
Kerouac also deals with themes of authority and order in these chapters. Sal, having moved to San Francisco and needing money, takes a job as a security guard, a part of the police force. This kind of job represents a completely opposite lifestyle from the one he lived in Denver and hoped to find in San Francisco. His fellow guards, former policemen who keep to a strict regimen and take delight in enforcing the law and making arrests, are characters whom Sal does not understand in the book. There is a clear dividing line between Sal and Remi, who steal and gamble and participate in the unruly behavior of the sailors they are supposed to keep in check, and the other guards, who apparently want only to enforce the law and take part in the law's power and authority. Kerouac insinuates that the pressures of work to make money and to live a certain lifestyle are unjust, pushing people into roles they are not suited for. Sal and Remi rebel openly against the growing pressures of consumerism by taking advantage of their positions and stealing groceries from the barracks cafeteria, justifying the theft by quoting Truman's advice that Americans should live more frugally.
Sal's relationship with Terry, a Hispanic migrant worker fleeing from an abusive husband, is a turning point for him in the novel. This relationship moves Sal even farther from his middle-class New York upbringing and is his first experience with the "fellahin" lifestyle, the lifestyle and culture of marginalized people. Sal falls in love and begins to identify with this person of a different race. While Sal's behavior up to this point was not the usual behavior of someone from his background, this relationship was even more likely to have been looked down upon in his home; it marks a true separation from his life in New York and reflects his new life on the road.
Interestingly, in Los Angeles, the two lovers revert to stereotypes, Sal believing Terry to be a prostitute and Terry believing Sal to be a pimp. This illustrates the racial misunderstandings that existed at the time, which Sal and Terry have a hard time overcoming despite their growing love and lust. In the end, Sal interprets their dispute and distrust as a "fit of sickness" so that the two can reconcile-and make love.
The end of Part One of the novel finds Sal becoming part of the marginalized culture of Hispanic America before returning to his life in New York. By falling in love with Terry and becoming her provider and protector, Sal comes to identify himself as a Chicano migrant worker just like Terry. Sal, perhaps unwittingly, begins to encounter the racism of Los Angeles. He and Terry cannot get jobs in town, and they eventually have to head for the farm country of California to find the only jobs available to them, laboring jobs in the fields. Sal immerses himself in the migrant worker life, earning little more than a dollar a day picking cotton and living in a migrant worker tent village.
To this point in the novel, Sal had been purposefully rebelling from the comfort and status that his race provided for him. He could party and freeload off of friends up to this point because he knew that money was readily available when he needed it. Yet, when Sal becomes a part of the marginalized community of migrant workers, he finds he no longer is able to take those same privileges. Food and money run out, and because he now identifies himself as Hispanic (even though Terry's family does not identify him as such), he is forced to take the only work available to him. Yet, when the cold of the winter begins to set in, Sal recalls that he is allowed the privilege of leaving the fields. This is a privilege that Terry and Terry's son do not have, and she is forced to beg her family to take her back while Sal returns to his family as something of a prodigal son (more or less) in New York. The divide between the races that Sal and Terry first experienced in Los Angeles ultimately drives them back to their initial homes and cultures.
The pastoral passages of the cotton field are Kerouac's attempt to idealize, perhaps unconvincingly, the discrepancies and tensions between races at this point in American history. Sal's adventure as a migrant farm worker does not encompass the harshness and desperation of such work for most at the time, instead illustrating an idyllic picture of the hard work of migrants. Instead of becoming truly immersed in the hardships of the culture, Sal only plays the role of a migrant farm worker. It is a role that he knows he will eventually leave.
As Sal arrives back in New York, he finds that he has not fully developed into the person he wanted to become. He has missed Dean, the inspiration for the journey, and now finds himself confronted again with the life of work and family he attempted to leave behind. His return home ends his first journey and Part One of the novel, yet Dean has already gone on ahead.