The town of Winesburg is described so clearly by Anderson that readers can easily imagine a map of the town (some texts actually include one). Basically the town is laid out like the letter H with Main Street forming the cross bar, the railroad forming the left leg, and Buckeye Street the right leg. Among the stores along Main Street, we can place the Winesburg Eagle office at the inner top corner of the intersection of Main and Buckeye Streets. Next to it is Hem's Grocery and, across from that, is Sinning's Hardware. Behind Sinning's is an alley that runs from Buckeye Street to the railroad where the railroad station faces the tracks. Behind the station is the New Willard House and in front of the station, across the tracks, is Biff Carter's Lunch Room. Moving back to Buckeye Street we can place the Fair Ground at the top outer edge of the H, and just below the Fair Ground is Waterworks Pond. Careful readers may be able to locate other landmarks in the town.
Critics have pointed out that in creating Winesburg, Anderson relied heavily on his memories of Clyde, Ohio, where he lived from the age of seven to nineteen. Both Clyde and Winesburg are eighteen miles south of Lake Erie; both have a Main, Buckeye, and Duane Street, a Heffer block and a Water works Pond; Clyde, in 1890, had a Gothic railroad station and a race track at the Fair Ground. Other things are strikingly similar. Alfred Pawsey's Shoe Store, Surbeck's Cigar Store, and Hurd's Grocery in Clyde became Win Pawsey's Shoe Store, Surbeck's Pool Room, and Hem's Grocery in Winesburg; Raccoon Creek and Piety Hill became Wine Creek and Gospel Hill.
In spite of these correspondences, however, Anderson evidently did not try to describe in minute detail the streets and business firms of Clyde, Ohio. Some critics have, in fact, complained that Anderson's work lacks "solidity of specification," and others have pointed out that, like Enoch Robinson, his creator preferred "the essences of things" to the realities. Anderson evidently wanted, perhaps for ironic effect, to preserve the impression of an idyllic pastoral setting, for the Winesburg he describes is like Clyde of 1890 — rather than 1896, when he left for Chicago. In fact, Clyde got electric lights in 1893, paved the Main Street that same year, and welcomed the opening of a bicycle factory in 1894, yet Anderson describes Winesburg as pre-industrial and talks, nostalgically perhaps, of the lamplighter moving slowly down the street.
The truth seems to be that the author of Winesburg provided enough realistic and specific details to make his reader accept this small Ohio town as credible, but he did not have the naturalist's penchant for scientific, detailed description and factual accuracy. His descriptions of alleys, fair grounds, lamp-lit streets, and cornfields seem to set the mood and create irony rather than preserve a moment of local history.