Past decades have seen an increase in focus on college and career readiness (CCR) policy and programming to meet the growing demand for a high-skill, global, 21st-century workforce. Recent research indicates many adolescents aspire to succeed in various postsecondary paths, but a persistent gap between aspirations and attainment remains. This is particularly true for traditionally underserved and underrepresented populations, such as those from rural communities. Looking beyond academic metrics such as test scores, grade point averages, and course offerings, this study seeks to address this gap by investigating rural adolescent school context and experience factors that may be associated with their academic motivation and CCR. A cross-sectional multivariate multiple linear regression analysis examining CCR and postsecondary choice factors was conducted using Mplus 8. Results from a large sample (N = 8,541) of rural adolescents from the Midwest United States found several variables--internalized and externalized behavior, peer relationships, parental involvement and support, and family/community connection--are positively associated with increasing favorable perceptions of academic motivation and college and career readiness. Study implications and directions for future research are offered.