Although Winesburg is a series of independent (albeit connected) stories, there is nonetheless a consistent mood from story to story—a mood of uncertain melancholy. It is a searching mood that reflects the larger anxieties of coming of age, which is an anxiety that pervades the story cycle. The mood also conveys the uncertainty and tremendous existential angst following the First World War. In addition, most of the characters in Anderson's stories have been marked, in some way, by tragedy. The important role of loss (and grief) in sustaining the melancholic mood of the stories is clear from the very opening of the book, as found in "The Book of the Grotesque":
For a time the two men talked of the raising of the bed and then they talked of other things. The soldier got on the subject of the war. The writer, in fact, led him to that subject. The carpenter had once been a prisoner in Andersonville prison and had lost a brother. The brother had died of starvation, and whenever the carpenter got upon that subject he cried. He, like the old writer, had a white mustache, and when he cried he puckered up his lips and the mustache bobbed up and down. The weeping old man with the cigar in his mouth was ludicrous.
Anderson portrays humanity at its most disoriented and pitiful in Winesburg, Ohio, and it isn't really until the reader can escape Winesburg (at the very closing of the book, when George Willard prepares to leave Winesburg for good) that the melancholy begins to dissipate in favor of a newfound optimism.
