This study uses an ecological systems framework to examine how indicators of individual, family, and school contexts are associated with post-secondary educational enrollment among a sample of rural youth. Structural equation modeling allows us to examine both direct and indirect effects of these contexts on school enrollment. Unique elements of the rural context lead us to expect associations between the family and school contexts and post-secondary school enrollment that differ from prior studies of urban youth. Findings of the current study are that: 1) contrary to existing studies of urban youth, indicators of family income and relationship with parents have only a small significant association with post-secondary school enrollment; 2) indicators of the school context have strong direct associations with student grades, aspirations, and self efficacy; and 3) the school context is a strong mediator in predicting post-secondary school enrollment. Implications for the existing research literature are discussed. (Contains 3 figures, 12 footnotes and 4 tables.)