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Maxwell Anderson's play won the 1935 Drama Critics' Circle Award. Burgess Meredith and Russian-born stage actor Maurice Moscovitch made their Hollywood screen debuts in this film. Meredith, Margo, Eduardo Ciannelli and Fernanda Eliscu appeared in the original New York stage production, and Myron McCormick replaced Ciannelli in the same show. Several reviewers noted the similarities between Anderson's play and the Nicola Sacco-Bartolomeo Vanzetti case. The New York Times review stated that the reference to the Italian Americans' infamous 1921 trial and their execution in 1927 after a reopening of the case was "thinly disguised." The play's tragic ending was altered for the film. In the play, "Garth" lives and both "Miriamne" and "Mio" are shot and killed by "Trock's" gunman. Although the film, which modern sources state was budgeted at $400,000, was billed as a successor to the critically and financially successful The Informer, it did not do well for RKO.
According to modern sources, Anne Shirley was first considered for the role of "Miriamne." Motion Picture Herald's "In the Cutting Room" includes Sidney Toler, Murray Kinnell and Bobby Caldwell as cast members, but their participation in the final film has not been confirmed. Art director Perry Ferguson and musical director Nathaniel Shilkret received Academy Award nominations for their work on the film. Film Daily voted the film one of the year's ten best in its annual poll of film critics.
Modern sources add Alan Curtis (Sailor), Arthur Loft (District attorney), Otto Hoffman (Elderly man), Al Hill (Gangster), Bobby Caldwell (Mio as a boy) and Grace Hayle to the cast. In 1948, the Mexican subsidiary of RKO released an adaptation of Winterset, A la sombra del puente, set in Mexico and starring Ester Fernndez and David Silva. Winterset was presented twice on television, in 1951 by the ABC broadcasting network, with Richard Carlyle and Eduardo Ciannelli, and in 1959 by the NBC broadcasting network and Hallmark Hall of Fame, with Don Murray, Piper Laurie and George C. Scott.