ABSTRACT: Structural inequalities in American public education are inextricably tied to deep-seated patterns of racial and economic segregation. Children in poor neighborhoods are less likely to have the household resources, neighborhood institutions, or school amenities necessary for a good, challenging education. In response, a growing number of organizations have launched initiatives to simultaneously revitalize neighborhoods and improve public education, emphasizing youth participation as an essential component in their efforts. We draw upon ethnographic data from two such organizations to examine their practice of place-based critical pedagogy in community development. We focus on how they engage marginalized, “hard-to-reach” youth via (1) experiential learning, to counter high-stakes testing models and cultivate a sense of ownership in the local community, and (2) empowered deliberative action, in contextualized ways. The tensions embedded in these organizations’ complex efforts have implications for other groups of marginalized youth engaged in community development, especially in their attempts to help students gain concrete outcomes in community development and achieve long-term sustainability.