Youth development programs offer flexible environments for healing and positive identity development for youth facing discrimination and oppression. Programs often occur in out-of-school time (OST), a context that is clearly positioned in tandem with the education system to create complex relationships that lead to challenges in OST spaces. Youth development programs occurring in OST settings have the potential for resisting or replicating oppressive practices toward youth occurring in the education system. This article highlights a youth participatory action research (YPAR) project within an OST program using photovoice, field trips, and arts-based strategies. Eleven youth participated in the project over the course of nine months. Thematic content analysis of weekly photovoice and critical consciousness resulted in a primary theme of peeling back the layers. This theme encompassed the evolution of youth understanding the interconnectedness between their individual-level experiences of racism and broader community and systems-level inputs. This article describes critical consciousness development of OST youth participants through intentional engagement in critical dialogue, experiential field trips, and reflective art making.