He was a member of the Dialectic Society and Pi Kappa Phi fraternity and predicted that his portrait would one day hang in New West near that of celebrated North Carolina governor Zebulon Vance, which it does today. Aspiring to be a playwright, in 1919 Wolfe enrolled in a playwriting course. His one-act play, The Return of Buck Gavin, was performed by the newly-formed Carolina Playmakers, then composed of classmates in Frederick Koch's playwriting class, with Wolfe acting the title role. He edited UNC's student newspaper The Daily Tar Heel and won the Worth Prize for Philosophy for an essay titled The Crisis in Industry. Another of his plays, The Third Night, was performed by the Playmakers in December 1919. Wolfe was inducted into the Golden Fleece honor society.
He studied playwriting under George Pierce Baker. Two versions of Wolfe's play The Mountains were performed by Baker's 47 Workshop in 1921.