It is widely acknowledged that the fictional model of the book's town, Winesburg, is based on Sherwood Anderson's boyhood memories of Clyde, Ohio, where Anderson lived between the ages of eight and nineteen (1884–1896), and not the actual town of Winesburg, Ohio located in the same state. This view is supported by the similarities between the names and qualities of several Winesburg characters and Clyde's townspeople, in addition to mentions of specific geographic details of Clyde and the surrounding area.
It is not known why Anderson chose the name Winesburg for the town in the book. What is known is that the name was not necessarily inspired by the stories themselves. In actuality, Anderson had been using Winesburg, Ohio as a base for Talbot Whittingham, the protagonist of an unfinished novel he had been writing on-and-off for several years prior to the composition of the Winesburg stories.
A direct relationship between the real Clyde and the fictional Winesburg, however, remains the supposition of scholars. Anderson wrote in A Writer's Conception of Realism that he reacted with "shock" when he "...heard people say that one of my own books Winesburg, Ohio, was an exact picture of Ohio village life." The author went on to admit that, "the hint for almost every character was taken from my fellow lodgers in a large rooming house..." These lodgers were the "...young musicians, young writers, painters, actors..." and others that lived in proximity to Anderson on the North Side of Chicago and to whom he referred as "The Little Children of the Arts". The truth probably lies somewhere in between, with memories of Clyde "merging" with Anderson's interactions at the boardinghouse.