Holden Caulfield seems to know his way around at least part of Manhattan. He seems relatively sophisticated for a sixteen-year-old boy. This suggests that he grew up right in Manhattan. He takes his knowledge of that towering city for granted. He is not impressed by the skyscrapers or anything else he sees. He is not at all like a tourist. He is not impressed by Broadway plays. He seems quite familiar with Alfred Lunt and Lynn Fontanne. He seems to know his way around. He has a certain savoir faire in dealing with taxi drivers, waiters, bartenders, and such. If he has taken trips out of town, he would have returned through Grand Central Station. He has ridden on the subways many times. Since he attended several private schools outside New York, he would have traveled to and from these schools by train through the heart of Manhattan. His family and many of his friends would also be New Yorkers. Salinger characterizes Holden as a real New Yorker. This was necessary to the plot, because Salinger didn't want to spend a lot of time explaining how impressed and disoriented his young narrator was by this huge, noisy, crowded, intimidating city. No doubt Holden has traveled around Manhattan on shopping trips, on some dates with girls, to see movies and stage playa, to visit various museums, and to various restaurants with his parents. He has been around a lot for a sixteen-year-old. But he had to be given a certain familiarity with the big city for plot purposes.

The disillusioned Holden Caulfied, having been expelled from a third prep school, wanders for a harrowing three days around New York City as he suffers from his teen-aged angst. His lack of direction in the city where he stays in hotels, bars, taxis, the homes of former acquaintances, and even Central Park where he worries what will become of the ducks in the winter, indicates the alienation and lack of direction that Holden senses in his life. It is not until he sneaks into his home and talks with his ten-year-old sister Phoebe that Holden stabilizes himself some.

In Chapter 10, for instance, Holden avoids the East side of the city where he would know people, so he takes a room on the other side of town at the Edmont Hotel that is "lousy with perverts." He describes his room as "crumbly," and with only a window to glance through. As he watches some of the lurid antics of people, Holden reflects how he does not really understand sex. Then, he goes to the Lavender Room, the cocktail lounge of the hotel,- and is critical of two girls who are on the watch for celebrities. He dances with one who is very good, but she pays no attention to him. But, although he is critical of these girls, Holden finds himself both repulsed and attracted to the superficial values of the adult world.

In Chapter 12, after his taxi cab ride Holden alludes to his loneliness as he points out how "quiet and lonesome" it is although it is Saturday night; his disillusionment is also notable as he ends the chapter with "People are always ruining things for you." Then, in Chapter 13, having wearied of desolate cabs, he walks a long way back to the hotel: "forty-one gorgeous blocks." Walking helps Holden, but he returns to his depression in Chapter 14 as he notes, "Boy, I felt miserable. I felt so depressed, you can't imagine."