In Michael Chabon's unusual novel, "The Mysteries of Pittsburgh," Art Bechstein has just finished college and is looking forward to a summer of freedom and play. He has left an unsuccessful relationship and finds himself free in his college town of Pittsburgh with an insignificant part-time job at a local bookstore and a new group of friends. His father belongs to the Mafia and, although Art tries to have a relationship with him, his father's shady background comes back to haunt him in unexpected ways. His mother died when Art was young, and his relationship with his father is only perfunctory and somewhat distant. Living in Washington, DC, his father comes for an occasional visit and lunch with Art. Art's "Uncle" Lenny, who seems to care for Art, resides in Pittsburgh.

Art's world, in his own eyes, has become colorful and fascinating now that he is free from school. He has an unusual fascination with the everyday people he meets and takes on as friends. As he watches events unfold, it is almost as if he is writing a novel with his life, seeing everything from the perspective of a newly liberated, almost grown young man, hungry for real-life experiences. He has been focused on academics for a long time, and being finished with that life feels surreal and liberating to him. Small details of the events in his life do not escape his notice, such as the bellhops in the extravagant hotel where he lunches with his father, who are dressed like monkeys.

In this story, Art befriends a young man named Arthur Lecomte, with whose social graces and homosexuality he is fascinated. He also meets Arthur's friends, one of them an alcoholic biker named Cleveland, whose bold exploits are legendary with this small group. Phlox, an odd and punkish young woman, becomes Art's girlfriend for a time. Arthur, Art, Phlox and their cohorts spend time walking the streets of Pittsburgh, exploring the "cloud factory," and the huge ravine where the most of Pittsburgh's poverty-stricken reside, and generally learning about life and the colorful array of people who live it.

The troubled biker, Cleveland is involved with criminal activity that is linked with Art's gangster father, and Art's father manages to intervene in a burglary. Cleveland is killed by a fall from the Cloud Factory tower, trying to outrun the police.

Art finally understands that his own mother was mistakenly killed by gangsters, as he truly realizes the sordid quality of activities his father's people are engaged in.

Ultimately, what Art is seeking is the meaning of true friendship, which is something he has never really experienced. The story of this particular summer is told as he recalls it, and he is sure, in the end that he has "exaggerated everything."