Many—all?—who grew up in the Midwest have had plans to leave it behind one day. Many—all?—who grew up in a small town in Middle America have had plans to find some place better. However, plans change and not everyone gets to leave. Sherwood Anderson brings that inner struggle into his writing, making the burden sympathetic through his use of simple, conventional language.
This is a semi-autobiography composed of a series of interconnecting short stories about life in a small town. The stories follow a main character from childhood to young adulthood, the moment he leaves Winesburg. He writes the stories as an adult looking back on his life and reminiscing on the past. Much of the stories are inner monologues that delve into loneliness, isolation, and the confines of small towns.