This paper is the personal journey of one teacher from a rural childhood, through a small university, to a rural school, and eventually to the city. It contrasts the intense challenges that rural teachers and students face with the unique opportunities afforded them by virtue of being rural. It includes an attempt to piece together the factors that influence high teacher transience rates in rural areas, a discussion of the pedagogical restrictions and freedoms offered by rural areas, and an exploration of possible ways that rural areas could reach out to their urban counterparts to help city kids understand their own inescapable connection to the land. Factors affecting transience rates include: (a) social isolation, long commutes, or both, (b) professional isolation, (c) demanding workloads as small staffs struggle to cover school responsibilities, (d) limited employment opportunities for life partners to find work in the same community, and (e) lack of long-term connection to the land. Pedagogical restrictions include (a) multi-graded classrooms, (b) demanding workloads, (c) limited budgets, (d) lack of professional support, and (e) the adverse impact of teacher transience on program continuity. Conversely, country schools offer many benefits: (a) small class sizes, which provide a unique opportunity to better understand children and how they think, (b) the potential for real-life contexts in which to embed many classroom experiences, (c) a less-restricted environment in which to explore innovative ways of teaching, and (d) a potential source of rich outreach to urban children regarding the world's food supply and our own connection to and dependence upon the land.