Dakota Sky (originally titled The Fifth Season) was developed in part by a 1994 New American Works Grant from the National Endowment for the Arts. It premiered at Olney Theatre in 1996, directed by Jim Petosa, and was the recipient of a Helen Hayes Nomination for best actress (Anita Hollander). It was awarded the 1996 Jane Chambers Playwriting Award (the first musical in the award's 13 year history to be so honored), and has been showcased by the Dramatist Guild in New York City.

"Among the show's assets is its highly American subject matter; not just in terms of history, but also the quintessentially American theme of reinventing yourself" - The Baltimore Sun