As we move into the 21st century, a largely unprecedented trend has emerged. Rural and urban schools, for so long faced with distinctly different challenges, have increasingly found themselves facing similar problems: a declining tax base, rising rates of linguistic and cultural diversity, deteriorating infrastructures, and inability to attract and retain qualified teachers, among others. Despite facing the same challenges, it is relatively rare to witness instances of rural and urban school collaboration. This essay uses an historical overview to identify obstacles to rural-urban school cooperation as a first step to improving the circumstances faced by both.