Due to the shortcomings of traditional schools, innovative supplementary (e.g. out-of-school, summer) programs have been identified as important sites for the positive development and learning of Black youth. This study foregrounds Black youth perspectives to offer additional insight into the role of supplementary programming. Drawing from 15 semi-structured, pre-post interviews with Black youth participating in a six-week summer CDF Freedom Schools program, we analyzed core distinctions drawn between youths' experiences in the program and in their traditional schools. Black youth attested to how the program expanded opportunities for them to express themselves, build community, engage in critical structural analyses, and imagine sociopolitical possibilities beyond the constraints of the present. We conclude with a discussion of implications, with an eye toward further specifying the types of educational contexts required to counteract detrimental aspects of traditional schooling and cultivate dispositions toward more just futures.