Edgar Lee Masters' 1915 collection of free-verse poems, Spoon River Anthology, was one of the most direct influences on Winesburg, Ohio. Published the year that Anderson started the book, each poem tells the story of a different citizen of a fictional town, Spoon River.

When Anderson was writing this book, between 1915 and 1919, Chicago was experiencing a literary renaissance. Among the writers of Anderson's circle of friends in those days, Floyd Dell is considered one of the most innovative. His 1920 novel, Moon Calf, is like Winesburg, Ohio in that it draws heavily on the author's past in a farm community, applying urban sensibilities and a sense of pity that comes from sophistication.

Although Winesburg, Ohio is considered Anderson's finest, most haunting work, he wrote many other novels, poems and short stones. His 1925 novel Dark Laughter is the most highly regarded work of...