In this paper we introduce a new way to conceptualize and measure the educational resources that young people encounter as they make their way from kindergarten to high school graduation. Using recent methodological advances in group-based modeling and a unique data set, we empirically test for and identify a series of categorically distinct school quality trajectories. We find that these trajectories vary significantly in terms of their intercept and slope, their prevalence within the sampled population, and in the sociodemographic makeup of their constituent members. We then present an extended empirical example illustrating relationships between school quality trajectories and important post-secondary educational outcomes, both before and after controlling for static, single-year measures of primary and secondary school characteristics. Our results suggest that the chronology of students’ exposures to different educational resources is significantly associated with college enrollment, college selectivity, and, in some instances, college completion.