Because Sherwood Anderson was so ambiguous about what directly influenced him, it is difficult to say that any specific writer or work inspired him to write Winesburg, Ohio as a whole. Still, most scholars affirm the obvious connection between Anderson's cycle and the Spoon River Anthology of Edgar Lee Masters (published in April 1915), which Anderson reportedly stayed up all night to read. Though B.W. Huebsch, Anderson's publisher, sent out a statement, upon the release of Winesburg, Ohio, heading off comparisons between the two works by stating (erroneously, as it turns out) that the Winesburg stories were printed in magazines before the Spoon River Anthology was published, the similarities in small-town setting, structure, and mood of the works have been noted by several reviewers, with one going so far as to call Winesburg, Ohio, the Spoon River Anthology "...put into prose."
Gertrude Stein, whose work Anderson was introduced to by either his brother Karl or photographer Alfred Stieglitz between 1912 and 1915, is also said to have played a key role in helping shape the unique style found in the stories. Through his interaction (at first satirizing it before ultimately accepting it as essential to his development) with Stein's Three Lives (1909) and Tender Buttons (1914), Anderson found the plain, unambiguous voice that became a staple of his prose. As indicated by the correspondence the two writers developed after the publication of Winesburg, Ohio, variations on the repetition found in Stein's writing in addition to their mutual appreciation for the sentence as a basic unit of prose were also likely features of her writing that Anderson noticed and drew upon in writing his Winesburg, Ohio. Literary critic Irving Howe summarized the pair's connection aptly when he wrote, "Stein was the best kind of influence: she did not bend Anderson to her style, she liberated him for his own."
Numerous other writers and works have been mentioned as possible sources from which the elements of Winesburg, Ohio were drawn, most of them either denied or unacknowledged by Anderson himself. The influence of Theodore Dreiser and the Russians (Chekhov, Dostoevsky, and Tolstoy) were discounted by the author, the former for stylistic reasons, the latter because he had apparently not read them prior to writing his book. While Anderson expressed an admiration for Ivan Turgenev's A Sportsman's Sketches, the affinities between Turgenev's novel and Winesburg, Ohio ("...both are episodic novels containing loosely bound but closely related sketches, both depend for impact less on dramatic action than on climactic lyrical insight, and in both the individual sketches frequently end with bland understatements that form an ironic coda to the body of the writing" ) may not be a sign of influence since it is not known whether Anderson read the book before writing Winesburg, Ohio. Finally, the regional focus on the Midwest has been linked to the writing of Mark Twain, particularly The Adventures of Huckleberry Finn, and while Anderson read and revered Twain, the connection between Twain and Winesburg, Ohio has largely been made by scholars seeking to place the book within the canon of American literature, not necessarily by the author.