Jane's trapped in her middle school computer lab playing "The Oregon Trail" for what feels like hours. The game becomes life and rips us back to the trail, 1848, where we travel in a covered wagon with Jane's great-great-grandmother. As Game moves us, back, forward, and back again, Now-Jane and Then-Jane's sadnesses are delicately juxtaposed in this play-meets-video-game about depression, Then and Now.