Life in death
Most of the figures share the similar history of a failed passion in life, of some kind or another. Many are lonely introverts who struggle with a burning fire which still smolders inside of them. The moments described by the short stories are usually the moments when the passion tries to resurface but no longer has the strength. The stories are brief glimpses of people failing.
The pastoral
The narrator often employs a theme of mock sentimentality toward the old, colloquial farmland that Winesburg represents as small town. More largely, it provides a background for examining the break down of the archetypal patterns of human existence: sacrifice, initiation, and rebirth.
Failure of absolute truth
Anderson believed that one should keep separate the worlds of realism and fantasy. He did not believe that an author could not write about both or about the collision of these worlds but he feared that authors would become stuck on realism or naturalism and forget about the importance of dreams, idealism, surrealism, and fantasy. Each of his figures grasped at least one truth as absolute and made it their mantra. The decision to base all of one's existence on an absolute truth transformed the figure into a grotesque and the truth into a lie.
Rebellion against values dominating American culture
The degeneration of communal bonds between people - sexual, familial, friendship, ritual modes of religion - was a common theme first traced by Anderson and then by many of the next generation (Hemingway, Fitzgerald, T.S. Eliot). It originated after World War I because of a disillusionment toward a modern society which was materialistic and business/industry oriented. The senses of modern men were anesthetized and they lacked personal identity. The isolated human of modernity was unfit for the love of men or community.
Winesburg as a microcosm of the universal
The figures of Winesburg were forced to handle issues and events which people universally underwent. Many common threads between man and between the self in relation to the world exist which the grotesque figures deal with in a manner to which any reader could relate. Winesburg then becomes Any Town, USA and the characters symbolize flaws and struggles in the universal human experience. Winesburg functions synecdochally for the typical human community.
