I understand this to be an American classic first published in 1919. Supposedly the writing of Sherwood Anderson influenced later writers such as Hemingway, Faulkner, Woolf, and Steinbeck. One thought that occurred to me is that he did for northern communities what Faulkner did for the South.
The book is a collection of short story descriptions of a variety of different people, all of whom live in the community of Winesburg, Ohio at the turn of the century. There is some interaction between the characters, but the stories are mostly descriptive in nature. All characters are described to be burdened with various foibles and idiosyncrasies. The story depicts the spiritual poverty of the industrial world and ignores the prevailing midwest values of the time.
If there's a message conveyed by the book it must be that life is a mess and the lives of everybody are lived in vain. Is the human condition really that bad?. It's pretty well wrapped up by the following quotation:"From being quite sure of himself and his future he becomes not at all sure. If he be an imaginative boy a door is torn open and for the first time he looks out upon the world, seeing, as though they marched in procession before him, the countless figures of men who before his time have come out of nothingness into the world, lived their lives and again disappeared into nothingness. The sadness of sophistication has come to the boy."
The one glimmer of possible hope for the future found in the book is in the final scene where a young man leaves the town. You have to think that surely things will be better anywhere other that there.