Winesburg, Ohio largely takes place in the fictional town of Winesburg, which is not based on the actual Winesburg, Ohio but likely on Anderson's own hometown of Clyde. With the exception of a few stories told in flashback, Winesburg, Ohio appears to be set at the time in which it was written—in the early 20th century, at the end of the First World War.
While some stories take place in other locations, including New York City, Winesburg is the heart and soul of the story cycle. Where other modernist writers of rural America portrayed the small-town Midwest as a series of tight-knit, insular, and cohesive communities, Anderson's Winesburg is borderline dystopian: this is a place of desolation, tragedy, and perpetual isolation, in which most characters are self-involved and self-destructive, and almost every character feels a deep and inexplicable sense of alienation from their families and peers. As the collection progresses and Anderson expands on the world of Winesburg to tell the stories of families who have lived in the town in generations past, it becomes clear that this is a perpetual affliction for the town. In fact, it's only at the very end of the collection—when George Willard prepares to leave Winesburg, likely for good, and the book's horizons show the promise of exploding outward—that the reader is able to see beyond Winesburg's dreary limits and feel the optimism of the world at large.
