There is a dearth of literature that examines rural youths' school transition and adaptation over the middle and high school years. Given rural education challenges, this study examines rural youths' developmental trajectories of self-reported grades and affective and behavioral educational outcomes (i.e., school belonging, value of education, school misbehavior, and extracurricular activity participation). The cohort-sequential study consisted of 3,312 African American and White youth (50% female) who were surveyed over three and a half years, including the transition to high school. The results reveal significant changes in the outcomes from sixth to twelfth grade. For example, on average, school misbehavior increased over time while perceived school belonging decreased over time. Gender and race differences emerged; African American youth reported placing higher importance on education and less participation in school activities than White youth. The discussion focuses on the importance of examining rural adolescents' educational pathways during the high school transition.