Researched utilizing a qualitative approach, this exploration into rural and urban teaching captures the experiences of eight Canadian teachers and their personal views concerning rural and urban schools. The groundwork preceding this study is described, the results of the study are presented, and a theoretical analysis of the research findings is discussed incorporating concepts of teacher identity, Deweyian philosophy, and socio-cultural ideologies. Via teachers' personal narratives, comparable and contrasting characteristics of rural and urban education are exposed. The information herein highlights the importance of community context when educators and educational stakeholders contemplate teacher and student behaviors. While expanding upon existing Canadian and international research conducted on the topic of rural and urban education, this study not only adds breadth to the subject matter, but a rich Western Canadian perspective. This contextualized study should be especially relevant to professionals within the field of education and readers with an interest in rural and urban education.