Declared among the best 25 American plays of the past 25 years by The New York Times, Underground Railroad Game begins in a very humble, even hokey way. A black woman sneaks fearfully into a barn, where she soon encounters a white man who is secretly helping her escape from slavery. With his stuck-on Quaker beard and corny lines, hints that she’s both not very bright and attracted to this man, and a basic set that’s as much made of cardboard as wood, it’s a relief when the lights come up and we discover it was a play within a play.

Middle school teachers Caroline (Jennifer Kidwell) and Stuart (Scott Sheppard) snap back into ‘reality’ and contemporary clothes. With a cheerfulness spiced with a little disciplinary severity, they tell the class, we the audience, that we’re going to play a game inspired by the Underground Railroad, the clandestine network of safehouses that helped American slaves to freedom during the 19th century.

Scott Sheppard and Jennifer Kidwell in Malthouse Theatre’s Underground Railroad Game. Photo © Ben Arons

Dolls representing slaves need to be moved to safehouse boxes by students randomly designated as Union...