On the Road begins with the two main characters of the novel, Sal Paradise and Dean Moriarty, meeting each other in New York after Dean has been released from reform school and he and his new wife, Marylou, have moved to New York. Dean is an eccentric and ecstatic character, a wannabe intellectual, who wants to learn to write from Sal and his group of friends in New York. After Dean and Marylou have a fight in which she reports to the police "some false trumped-up hysterical crazy charge," Dean moves in with Sal to Sal's aunt's house. The stay is short, however-Dean soon meets Sal's friend Carlo Marx and begins to spend all his time with him. Dean and Carlo become fast friends, and Dean becomes hysterically excited with life in New York, sharing intellectual ideas, writing, and chasing women. He does all this while working as an attendant at a parking lot, a job he undertakes with recklessness. Sal believes Carlo and Dean are mad but follows them because they are interesting. To Sal, Dean and Carlo are people who "burn, burn, burn like fabulous yellow roman candles." Their intensity and, often, insanity drive Sal's curiosity and yield the definition of what it means to be Beat.
As spring approaches Dean leaves New York to travel back West. Realizing that his time hanging around his college campus needs to end and that he needs new experiences and ideas as a writer, Sal decides that later in the spring he will join his new friend Dean in his travels. In July of 1947, with fifty dollars in his pocket, Sal leaves New York for San Francisco. He decides to take Route 6 and hitchhikes to the road's beginning in upstate New York. After getting drenched in a rain storm, he hitches another ride back to New York, realizing that Route 6 doesn't have enough traffic to take him where he wants to go. He swears to be in Chicago by the next day, however, so he spends most of his money on a bus ticket to make sure.
After taking a bus to Chicago, Sal spends a day exploring the city before hitchhiking to Davenport, Iowa. Catching rides with a pair of truckers and a group of college boys from the University of Iowa, Sal ends up in Des Moines the morning, where he gets a cheap hotel room in which sleeps through the day. As he wakes at dusk, he has the distinct feeling that he does not know who he is anymore: "I was far away from home, haunted and tired with travel ... I wasn't scared; I was just somebody else."
Looking forward to meeting his friends in Denver, Sal quickly leaves the hotel and hitches a ride with a new friend he meets, an enthusiastic New Yorker named Eddie who tells dirty jokes and reminds Sal of his cousin from the Bronx. Eddie and Sal hitch rides through Iowa and Nebraska and meet up with a cowboy who wants them to drive an extra car through Nebraska where he plans to meet his wife. Eddie drives, a little too fast, and after several hundred miles on the road and a stop at a roadside diner, Eddie and Sal hitch more rides into Shelton, Nebraska, where they get stuck.
After being solicited for work by a carnival owner, a Nebraska farm trailer going to Denver comes by and offers a ride to only one of the men. Without even discussing it, Eddie jumps on the wagon and takes off with a shirt Sal had let him borrow. Sal waits in Shelton until a young guy gives him a ride a hundred miles closer to Denver.
As chapter four opens, Sal gets the "greatest ride" of his life on a "flatboard" truck headed to Los Angeles full of hitchhikers: farm boys on their way to the harvests, high school kids hitchhiking for the summer, Montana Slim, Mississippi Gene and his charge, and boxcar hobos. Only a quick stop to eat and buy whiskey interrupts the drive into Colorado. As they drink and laugh, playing practical jokes on each other while trying to urinate over the side of the truck, Sal and Mississippi Gene realize they have a common friend in a hobo named Big Slim, who "punches cows" in East Texas. Sal befriends Mississippi Gene and his charge and gives all his cigarettes to them. As Sal begins to get more and more excited about getting to Denver, they all continue to drink. They bundle up under a tarpaulin to keep from freezing in the cold Colorado night. When the truck reaches Cheyenne, Wyoming, Sal and Montana Slim jump off the truck to explore the celebrations of Wild West Week in the town.
The first two chapters introduce the reader to the main characters of the novel, Sal Paradise and Dean Moriarty. Sal, as a writer, is fascinated with interesting people and new experiences. Dean, spontaneous in his appetites for food, sex, drugs, and life, becomes a fascination for Sal and spurs his desire to travel.
The opening chapters also present an overview of the lifestyle of the "Beat Generation." It is an ecstatic and stimulating lifestyle based on experiencing and living life, often involving sex and drugs. But it is also an intellectually stimulating lifestyle in which ideas and writing share primary importance. Dean and Carlo Marx share an especially deep intellectual kinship. As Sal prepares to begin his journey on the road, we see Sal as a character who is beginning to separate from his life as a student, a member of a working-class family, and a reclusive writer. Sal's aunt believes Dean is a bad influence but encourages the trip anyway. Sal becomes hungry for the lifestyle and adventures that he is sure his friends are having in the broad landscape of America.
Sal's initial mishap on his journey, choosing the wrong route, getting stuck in the rain, having to return to New York, and eventually spending most of his money on a bus ticket to Chicago, highlights his early naivete and eagerness to join the beatnik lifestyle. The reader will soon experience with Sal, though, a full immersion in the beatnik culture of America.
Chapters three and four introduce the reader to the sights and characters of the road as well as Sal's evolving character as he begins his journey. In several instances the reader is made aware of Sal's progression from an East Coast college kid into an example of the Beat lifestyle. Through chapters three and four Sal mentions that he only ate pie and ice cream during this first trip, an allusion to childhood choices. Eddie, the friend he meets outside of Adel, Iowa, reminds him of his family back East and gives him some comfort on the trip. In a cheap hotel in Des Moines, after crossing the Mississippi River (the gateway to the West), the first changes begin to take root in Sal's character. He wakes up in the hotel to find that he no longer knows who he is; he feels like a different person. While this transformation will continue to develop throughout this first cross-country journey, this moment marks a turning point for Sal from his New York life to his beatnik life.
As the trip progresses west, the characters begin to take on personalities that mirror the landscape. The Iowa truck drivers are loud and boisterous, and so is the cowboy in a diner in Nebraska. "I said to myself, Wham, listen to that man laugh. That's the West, here I am in the West," Sal says as he listens to the cowboy entertain the others in the diner. The reader also is introduced to the slowly fading culture of the Old West. As Sal pulls into Cheyenne, Wyoming, he is greeted by the Wild West Festival, a celebration that he sees as sadly trying to recreate a time that is already gone.
Sal's fellow hitchhikers on the truck headed to Los Angeles also begin to represent the underbelly of a country Sal had not known in New York. Mississippi Gene and his charge are running from the law, and poor hobos cannot afford to buy food-they all contrast starkly to the diner full of pretty girls whom Sal sees at a stop in Colorado. As Sal continues on his journey to Denver, readers begin to see a segment of the American heartland who live on the fringes of society.