The Oregon Trail is about two girls named Jane. One is a Middle Schooler sitting in a familiar 90s computer lab, experiencing boys and body odor for the first time, playing the seminal computer game of our childhood: The Oregon Trail. The other actually lives inside the game, living life on the trail, moving across the country after the death of her mother towards a new life in Oregon. Both dealing with an ineffable sadness, a feeling like their choices are not their own. The game itself pushes them inexorably through time, like a digital god - Present Jane deals with apathy, unemployment, and daytime television. Past Jane deals with dysentary, dead oxen, and whether or not to ford the river. Can either claim a life worth living before the game is over? A wry millenial look at nostalgia, growing older, and a sadness that carries across generations.