The effectiveness of the federal Head Start preschool program has been studied extensively for more than five decades. However, several areas of research need further consideration. First, a focus on Head Start's effectiveness in rural communities is needed because of the unique challenges and affordances of life in rural America as well as documented variation in the effects of Head Start between urban and rural regions of the US. Second, the sustained effects of Head Start may depend on access to high-quality educational environments in elementary school, but this topic has not been studied extensively and the extant findings are mixed. The overarching aim of this study was to examine the effects of Head Start participation in relation to children's academic and social-behavioral skills in the spring of pre-kindergarten (pre-K) and in the spring of kindergarten as well as the educational characteristics of kindergarten classrooms and elementary schools that may help to sustain the long-term effects of Head Start.