The cycle consists of twenty-two short stories, one of which consists of four parts:[note 1]
- The Book of the Grotesque
- Hands—concerning Wing Biddlebaum
- Paper Pills—concerning Doctor Reefy
- Mother—concerning Elizabeth Willard
- The Philosopher—concerning Doctor Parcival
- Nobody Knows—concerning Louise Trunnion
- Godliness
- Parts I and II—concerning Jesse Bentley
- Surrender (Part III)—concerning Louise Bentley
- Terror (Part IV)—concerning David Hardy
- A Man of Ideas—concerning Joe Welling
- Adventure—concerning Alice Hindman
- Respectability—concerning Wash Williams
- The Thinker—concerning Seth Richmond
- Tandy—concerning Tandy Hard
- The Strength of God—concerning The Reverend Curtis Hartman
- The Teacher—concerning Kate Swift
- Loneliness—concerning Enoch Robinson
- An Awakening—concerning Belle Carpenter
- "Queer"—concerning Elmer Cowley
- The Untold Lie—concerning Ray Pearson
- Drink—concerning Tom Foster
- Death—concerning Doctor Reefy and Elizabeth Willard
- Sophistication—concerning Helen White
- Departure—concerning George Willard
The book is written as a third-person omniscient narrative with the narrator occasionally breaking away from the story to directly address the reader or make self-conscious comments (in "Hands", after describing the poignant nature of the story, he writes that "It is a job for a poet",[48] later in the same story adding, "It needs a poet there".[49]) These remarks appear less often as the book progresses.[50]
Though each story's title notes one character, there are a total of over 100 characters named in the book, some appearing only once and some recurring several times. According to literary scholar Forrest L. Ingram, "George Willard [recurs] in all but six stories; 33 characters each appear in more than one story (some of them five and six times). Ninety-one characters appear only once in the cycle (ten of these are central protagonists in their stories)."[51] Within the stories, characters figure in anecdotes that cover a relatively large time period; much of the action takes place during George's teenage years, but there are also episodes that go back several generations (particularly in "Godliness"), approximately twenty years ("Hands"), and anywhere in between. Indeed, the climactic scenes of two stories, "The Strength of God" and "The Teacher", are actually juxtaposed over the course of one stormy January evening. As Malcolm Cowley writes in his introduction to the 1960 Viking edition of Winesburg, Ohio, Anderson's "...instinct was to present everything together, as in a dream".[52]
