The stories are set in the fictional town of Winesburg and revolve around the character of George Willard, a young newspaper reporter. Through George's interactions with the town's residents, Anderson explores themes of isolation, loneliness, and the difficulties that surround human connection.

Sherwood Anderson’s book of interconnected short stories Winesburg, Ohio tells the story of a town through portrayals of a half-dozen of its most notable residents. The book is narrated by town reporter George Willard, who, having grown up in Winesburg, decides to abandon the town as an adult. Overall, the book is concerned with the faulty nature of the absolute truths grasped at by the characters in Winesburg, Ohio which become their downfall each story. Written in 1919, the stories take place around the same period.