Ray Bradbury has credited Winesburg, Ohio as an inspiration for his book The Martian Chronicles.
H. P. Lovecraft said that he wrote the short story "Arthur Jermyn" after he "had nearly fallen asleep over the tame backstairs gossip of Anderson's Winesburg, Ohio."
Israeli writer Amos Oz writes in his biography A Tale of Love and Darkness that Winesburg, Ohio had a powerful influence on his writing, showing him that literature must not necessarily always be about heroes. Only after reading Anderson did he find the courage to start writing.
Philip Roth's 2008 novel Indignation is set, in part, at Winesburg College in Winesburg, Ohio. His protagonist holds a part-time job as a waiter at the "New Willard House", evoking the protagonist, George Willard, of Anderson's book.
Henry Miller references the book on the first page of his novel Sexus (of The Rosy Crucifixion series).
In the 1985 film Heaven Help Us, Danni reads a passage from "Sophistication" to her grief-stricken father.
In the 2003 film The Best of Youth (La meglio gioventù), Matteo Carati borrows Raconti dell'Ohio, the Italian translation of the book, from the library in Rome where he sees Mirella for the second time.
In the ABC television series, Pretty Little Liars, the book is given to the character Aria Montgomery by her English teacher, Ezra Fitz, with whom she is having an affair. He writes the inscription "When you need to leave Rosewood... Ezra" on the first page.
Porter Shreve presents a possible sequel to Winesburg, Ohio in his novel The End of the Book.