After stopping for a day and night in Chicago, where he walks around and listens to some bop music, Sal takes the bus to Illinois, and from there, hitchhikes to Davenport, Iowa, where he sees his much-dreamed-of Mississippi River for the first time. After standing on a beautiful but empty crossroads until dusk, Sal decides to try where the big trucks pass by the gas stations. He's in luck, and a garrulous truck driver picks him up. Sal enjoys the ride, sitting up high in the cab and yelling back and forth with the truck driver. The truck driver blinks his lights to signal another truck driver behind them, and Sal switches trucks at Iowa City: another driver just like the first. Finally, Sal's going west fast. The second driver drops him off in Des Moines. Sal tries to get a room at the Y, but they're full, so he ends up in a grungy hotel by the railroad tracks, where he sleeps all day. At sunset, he wakes, exhausted, with a strong feeling of disorientation: for about fifteen seconds, he has no idea where he is, or even who he is.
He packs his bag and keeps moving. He eats a meal of apple pie and ice cream--all he has been eating on his trip--and sees beautiful Des Moines girls everywhere he looks, but he's in a hurry to get to Denver. Hitching again, he meets Eddie, a "rednose young drunk" from New York, and they decide to hitch together. They get stuck in another small town and stop at a bar. Eddie gets drunk and joyous. They try to hitch again with no success, so finally Sal pays for them both to take a bus to Omaha. They keep hitching. One of the rides is with a cowboy-type, who tells Sal about how he used to hop freight trains during the Depression. At a diner, Sal sees a big Nebraska farmer with a huge booming laugh who seems to him to be the spirit of the West. They get stuck briefly in Shelton, where it is raining, and Sal lends Eddie a shirt. A carnival owner asks them if they want to work with the carnival and they decline, but laugh about the idea afterwards. The next ride only has room for one, and without a word, Eddie takes it.
Sal, alone again, catches what he considers the greatest ride of his life, on a flatboard truck driven by two smiling young farmers on their way to Los Angeles, who are picking up everyone they see. The back is filled with characters, including the sneaky-looking "Montana Slim" and the kind hobo "Mississippi Gene." Gene is taking care of a quiet young boy; Sal likes them and buys cigarettes for them. They have a rollicking time, only stopping for food and "pisscalls". At one stop, they chip in together to buy a bottle of whiskey. Sal watches the landscape change in the open air from farmlands to the rangelands of the plains; he's never seen anything like it. At one point, Montana Slim has to pee. The farmers don't stop, so he decides to go over the side. Someone alerts the farmers, who swerve back and forth so Montana Slim pees all over himself, which is funny to everyone except for him. Finally, with Sal drunk and looking at the stars, they arrive in Cheyenne. Sal and Montana Slim get off, and the truck goes off into the night.
Sal and Montana Slim hit the bars. Sal tries to pick up a Mexican waitress, but she puts him off kindly. They go to another bar and pick up two plain girls. Sal is getting more drunk and spends all but his last two dollars, wanting to sleep with one of the girls, but she isn't interested. Sal falls asleep in the bus station. He wakes alone and goes out to the highway to hitch again. He's sick and hungover at first, but feels better when he gets to Longmont, Colorado. After a nap on a patch of grass in front of a gas station, he looks at the Rockies and feels more and more excited, anticipating Denver. He is full of joy when his next ride lets him off at Larimer Street, in Denver.
Sal's adventures west begin. The descriptions of the places he passes through are full of exuberance. The long sentences and paragraphs convey the feeling of constant, rolling motion (keep in mind that Kerouac typed a draft of On the Road on one 50-foot long roll of paper). The only lull occurs, briefly, when Sal is in the Des Moines hotel and wakes up not knowing who or where he is. He says he is halfway across America, "at the dividing line between the East of my youth and the West of my future." The geography parallels Sal's emotions: he is opening up, giving forms to what were before just ideas and dreams. He feels this everywhere: as he goes West, even his staple dish of apple pie and ice cream is getting bigger and better. Every character he meets is not only an individual, but an epitome of a region, a way of living, like the laughing Nebraska farmer in the diner. Everything is described in superlatives: "incredible," the best, the hugest, the sweetest, "the prettiest girls in the world." Sal is making a personal pilgrimage; Denver is the Promised Land, San Francisco is an even greater "vision," the Nebraska farmlands are like the Nile Valley. He is going to Denver, the birthplace of Dean, who is the avatar of Sal's vision of the West.
Sal's compassion and clear-eyed tolerance manifest more clearly in this section. Because he sees Mississippi Gene as gentle and kind and feels sorry for the boy Gene is taking care of, he goes out of his way to be considerate to them, offering them whiskey and cigarettes. Sal knows right from the start that Montana Slim is "sneaky," and Slim proves this by bragging about being a mugger. Yet, this doesn't stop Sal from enjoying Slim's company in Cheyenne. He even revises his opinion slightly, observing how Slim dutifully writes a postcard to his "Paw."