Sherwood Anderson began writing the short stories, relatively in order, during the late fall of 1915. The majority were finished by the middle of 1916. The story "Godliness" was not originally written as part of the collection but was salvaged by Anderson from a failed novel attempt in 1917. Many of the tales were based on a life Anderson had witnessed in Clyde, Ohio, the town where he spent most of his childhood and adolescent years. The hero's mother, Elizabeth Willard, dies at the same age as Anderson's mother did. The impressions he gained from the town life and character of Clyde explains why he gave the book the subtitle, "A Group of Tales of Ohio Small Town Life."
The book however was written while Anderson was in Chicago, three to four years after his mid-life crisis of 1912. After this event, he left his life in Elyria, Ohio and returned to Chicago, with his family, to his old job writing advertisement copy. Though he did not reject business values completely as he liked to claim after his breakdown, he did give much more time to his creative writing hobby and was able to publish his first book, a novel Windy McPherson's Son, in 1916. Marching Men, his second novel, and the first book he published were considered by Anderson to be immature works of which he was never really proud. Often throughout Anderson's career, however, he would publish works that he knew were flawed and was thus often criticized by critics who were not able to separate his weaker works from the fine ones. Winesburg, Ohio has since been acclaimed a timeless classic with generational and universal themes, illustrating that even as Anderson wrote his first two novels he was also creating a quality text.
Although Anderson was writing about Ohio small town life in Winesburg, Ohio, he was also commenting on urban America and the isolation of modern society the post-World War I generation was disillusioned by and would discuss in detail following Anderson's great work. Thus the stories intermingle small town and urban America in a truly universal way. Unlike the first novels he wrote, manuscripts show that Anderson spent a good amount of time editing and revising Winesburg, Ohio. He was heavily influenced by Gertrude Stein, whom he considered to be a "writer's writer", and tended to experiment with words in much of the same manner she was known for in her work, Tender Buttons. To him, Stein was a pioneer of literature who made him aware of the hollowness of conventional American language. Anderson diverges from a traditional use of syntax, form, rhythm, and plot mainly because of the lessons he learned from Stein.
The generation following Anderson would thus pick up on not only his pioneering sense of story but Stein's pioneering sense of language, and its deterioration of meaning. One can easily see this move away from conventional structure and voice in the works of Anderson, James Joyce, Ernest Hemingway, William Faulkner, E.E. Cummings, and the Dadaists. Anderson has been noted as the only storyteller of his generation to have a great effect on the style and themes of the following generation. The structure Anderson employs in Winesburg, Ohio was also borrowed from Edgar Lee Masters' Spoon River Anthology which presented a series of character sketches in elegy form. Other works of literature which likely influenced Anderson's text are Turgenev's A Sportsman's Sketches, the works of Hawthorne which also portrayed the grotesque, and E.W. Howe's The Story of a Country Town. Anderson's Winesburg, Ohio grows from these preceding texts and adds a "precise, ironic voice offering delicate accounts of grotesque human creatures."
Furthermore, Anderson was a writer that depended overwhelmingly on his inner emotions. His writing as result tended to be unclear and scattered in many cases before and after Winesburg, Ohio. With all of his writing, he wrote, with very little control, from an inner voice which dictated what came out onto paper. Winesburg, Ohio came about in an illuminated moment, much like the episodes Anderson writes about in the text. As he described it, he was walking along a lonely Chicago street after learning that he was fired from his job. Arriving home, he sat down and wrote the short story "Hands" all at once. Afterwards, he never changed a word. Walking the streets immediately after he finished the story, the world seemed bright and beautiful. Little magazine editors picked up his stories before he published them in the collection. Floyd Dell, the editor of Masses and a friend of Anderson's, printed three stories in 1916, starting with "The Book of the Grotesque." Four tales were published in 1916 and 1917 by Waldo Frank in Seven Arts. The Little Review printed two stories in 1916 and 1918. The small but supportive audience he gained, young and in favor of his rebellion versus traditional American literature, allowed for a receptive welcome when B.W. Huebsch published Winesburg, Ohio in 1919.