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This paper introduces “#CommunityCrawls,” a public humanities initiative that connects youth to community spaces like museums, parks, and libraries. These spaces are meant to serve as accessible out-of-school time (OST) environments for learning, recreation, and creativity. However, their potential is limited if youth do not find them inviting or useful. Using connected learning theory, #CommunityCrawls emphasizes digital storytelling to boost youth engagement. Over three weekends, five South Side Chicago teens documented their OST experiences on TikTok. Analyzing TikTok videos, observational data, and conducting semi-structured interviews, preliminary findings reveal that spaces perceived as “fun” encouraged exploration and creativity, while “boring” spaces deterred participation. This research aims to empower youth, bridge gaps in OST engagement, and enhance the appeal of community spaces.