Where is Holden at the beginning of The Catcher in the Rye?

As the novel opens, Holden is standing beside a Revolutionary War-era cannon on top of Thomsen Hill, looking down at the football field where "practically the whole school except me was there." This is an appropriate setting for the opening because it shows how Holden is symbolically isolated from his school and, by extension, the whole world. Holden explains he has been "ostracized" by the Pencey fencing team because he lost their equipment on the subway while they were on their way to a match with a school in New York City. Holden talks about Pencey Prep in his usual tone of adolescent pseudo-cynicism. The reader can tell this boy is unhappy and that his critical view of almost everything is due to his loneliness and feeling of being "ostracized." He shows his interest in girls by his description of the students attending the football game.

There were never many girls at all at the football games. . . . I like to be somewhere at least where you can see a few girls around once in a while, even if they're only scratching their arms or blowing their noses or even just giggling or something.

This explains that Pencey is for boys only. The football game in progress establishes that the time of year is fall. Holden tells us it is December and the weather is extremely cold. The cold weather and Holden's isolation set the tone for the entire novel. He has been kicked out of Pencey and is literally and figuratively out in the cold. He will spend most of the novel in Manhattan trying to find relief from his loneliness by talking to strangers and looking up the few people with whom he has some tenuous relationship. This big city is hardly a good place for a stranger to find a friend.

Holden has a combination of intelligence and naïveté. He doesn't know what he wants or where he is going. He seems to be lost in the city's looming, intimidating buildings. Even though Holden feels "ostracized" by the whole school, it is still a sanctuary compared to Manhattan. Salinger devotes the first seven chapters of The Catcher in the Rye to a description of what appears to be a typical upper-class prep school to show its contrast with the Manhattan jungle. When Holden leaves Pencey, he will be making a great leap into adulthood. Manhattan will become his "school" for the rest of the novel.