A TV version was made in 1973 directed by Ralph Senensky and starring Joseph and Timothy Bottoms as George Willard, Jean Peters as Elizabeth Willard, Curt Conway as Will Henderson, Norman Foster as Old Pete, Dabbs Greer as Parcival, Albert Salmi as Tom Willard, Laurette Spang as Helen White, and William Windom as Dr. Reefy.
In 2008 Winesburg, Ohio, a filmed adaptation of the novel, was produced by Jennifer Granville. It was screened at the Athens International Film and Video Festival. A companion documentary, Lost in Winesburg, directed by Tommy Britt, examined the legacy of Anderson's book by documenting present day small town Ohio and the attempt to adapt Anderson's book for the screen by the local community and Ohio University students, alumni, staff and faculty.
In 2010, Chicago Heights, a contemporary adaptation of the modular novel, premiered in competition at the Busan International Film Festival and appeared in multiple additional festivals. Noted film critic Roger Ebert said "it is a beautiful book, and has inspired this beautiful film," and later listed Chicago Heights among the Best Art Films of 2010. The film was directed by Daniel Nearing, written by Nearing and Rudy Thauberger, and stars Andre Truss, Keisha Dyson and Gerrold Johnson.
A stage adaptation of Winesburg, Ohio by Sherwood Anderson (initially in collaboration with playwright Arthur Barton) was performed at the Hedgerow Theatre in Rose Valley, Pennsylvania in 1934. Directed by Jasper Deeter, it achieved some success, running from June through September of that year. Charles Scribner's Sons published this version of the play alongside three one-act plays (Triumph of an Egg, Mother, and They Married Later), also by Anderson, as Plays: Winesburg and Others in 1937.
A Broadway production played for 13 performances in February 1958 at the Nederlander Theatre (then known as the National Theatre). The adaptation, written by Christopher Sergel, starred Ben Piazza as George Willard, James Whitmore as Tom Willard, Sandra Church as Helen White, and Leon Ames as Dr. Reefy.
Four of the stories from Winesburg, Ohio were staged in 2001 at the Julia Morgan Theater in Berkeley, California. Word for Word Performing Arts Company and the Shotgun Players adapted "A Man of Ideas", "Paper Pills", "Surrender", and "Hands". The production was nominated for five San Francisco Bay Area Theatre Critics Circle Awards (Entire Production – Drama, Supporting Performance – Female, Director, Sound Design, and Ensemble Performance).
The whole cycle was adapted into a musical and premiered in 2002 at the Steppenwolf Theatre in Chicago, Illinois. The book and lyrics were written by Eric Rosen (in collaboration with Andrew Pluess, Ben Sussman, and Jessica Thebus). Following its 2002 premiere, the musical was featured as part of the About Face Theatre Company's 2003–2004 season. The About Face production received the two Jeff Awards for New Adaptation and Actor in a Supporting Role-Musical. A 2006 production of the musical by the Arden Theatre Company (Philadelphia) won the Barrymore Award for "Outstanding Musical".
A loose musical adaptation of Winesburg, Ohio written by Kevin Kuhlke with music by Heaven Phillips premiered in 2003 as Winesburg: Small Town Life at the Perseverance Theatre in Juneau, Alaska.