Edgar Lee Masters' 1915 collection of free-verse poetry, Spoon River Anthology, significantly influenced Winesburg, Ohio. Released the same year Anderson began his book, each poem in the collection narrates the life story of a distinct resident of the fictional Spoon River town.

During Anderson's writing period from 1915 to 1919, Chicago was undergoing a literary renaissance. Among Anderson's literary friends, Floyd Dell was considered particularly innovative. His 1920 novel, Moon Calf, shares similarities with Winesburg, Ohio by drawing heavily from the author's experiences in a rural community, incorporating urban insights and a sophisticated sense of empathy.

Although Winesburg, Ohio is regarded as Anderson's most haunting and finest work, he authored numerous other novels, poems, and short stories. His 1925 novel, Dark Laughter, is his most esteemed piece of long fiction and was his most financially successful work during his lifetime.

Ernest Hemingway viewed Anderson as a friend and mentor. Anderson introduced Hemingway to Gertrude Stein and other European authors who later became integral to the Hemingway legacy. Hemingway's 1925 story collection, In Our Times, reflects the influence of Winesburg, Ohio through its interconnected stories that revolve around a central character and theme.

Anderson wrote several autobiographies, but the one he worked on for nine years before his death is considered the most significant. Initially published in a heavily edited form, as Anderson's literary reputation grew, his original writings were restored. The revised edition was published in 1943 as Sherwood Anderson's Memoirs.

Irving Howe, a highly respected literary critic, published Sherwood Anderson: A Biographical and Critical Study in 1951, with a new introduction added in the 1966 edition. While his analysis of Anderson and his work is not the sole interpretation, he offers a concise, insightful, and thorough explanation that is accessible to students.