Two for the Road brings together a pair of thematically related novels, Man and Boy (1951) and In Orbit (1967), each of which concerns a rural American community's response to petty tyranny.

Man and Boy is the story of a woman, Mrs. Violet Ames Ormsby, whose overbearing personality permits only two responses from the men in her life acquiescence or rebellion. Although her husband self-effacingly defers to her, her son, Virgil, acts out against her; indeed, he frustrates her grand intentions for him by dying heroically in the Second World War.

In In Orbit, a small Indiana town is struck by an uncontrollable force of nature: a delinquent draft-dodger named Jubal Gainer. Gainer rides into town "his arms high and wide, his ass light in the saddle of a stolen motorcycle," and within twenty-four hours has raped a half-witted woman and stabbed a storeowner, not with any premeditation, but because they happened to cross his path. Each taking his own turn, the stunned townspeople tell the story of "the day the tornado hit" as if they were members of an ancient Greek chorus.