Winterset was a success on Broadway and was largely met with reviews that praised Anderson's ability to combine poetry with realistic contemporary drama. Some critics found the play's Shakespearean themes jumbled and its poetic voices unconvincing, but these critics were in the minority. In 1936, the play was awarded the newly created Drama Critics' Circle Award, which led to its popularity across the country for five years. Later critics, while sometimes finding fault with aspects such as its melancholy ending, tended to agree that the play was one of Anderson's finest achievements and one of the best American verse dramas of the twentieth century.

In his article, "Winterset and Some Early Eliot Poems," Perry D. Luckett characterizes the substance of the critical approaches to the play as follows:

Critics initially concerned themselves with its use of verse, a major experiment in a theater devoted largely to prose...