Oregon Trail: The Play! is an irreverent comedy honoring/skewering that most traumatizing/beloved of educational video games from the 1980s and 90s. The play follows the Bootsmeyer family (fatherly Ezekiel, godly brother Jebediah, obligatory-female-character Martha, young ragamuffin Judah, and Old Crazy Fingers) as they set off in the year eighteen somethin' something on a troubled journey westward. Narrated by an inexplicably omni-present general store owner, this dark comedy takes the audience through familiar territory, as the Bootsmeyers stock up on provisions for their oxen-led wagons and do their best to survive river crossings, illnesses, hunting, highway robbery, and a host of other mid-nineteenth century dilemmas. Throughout, Allegra's parody of the game's (and American history's) casual sexism, racism, and depletion of natural resources is intentionally uncomfortable, but to enjoyable ends. Nostalgia will wax as audiences hunt mid-play in a nerf shooting gallery as surely as squeamishness will strike when dysentery jokes pile high. Oregon Trail: The Play! pays homage to the American traditions of Westerns, dysfunctional families, and cross-country road trips, but above all else offers tribute to the beloved game played by so many millions in school.