Playful Learning Landscapes (PLL) merges playful learning pedagogy with community spaces to create playful learning opportunities for children, families, and communities. Prior PLL projects have demonstrated effectiveness in enhancing social interaction between children and caregivers by creating opportunities for social interaction derived from the learning sciences literature. In the present case study, a university-based team of PLL researchers partnered with a local community-based organization (CBO) that provides educational, skill building, and job training opportunities for teens in low-income neighborhoods. PLL provided consultation and training to transform the CBO’s Play Captains program into a Playful Learning program where local teenagers led playful learning activities for children on city streets (Play Streets) that were closed to vehicular traffic by Philadelphia’s Parks and Rec department. The teen Play Captains also conducted research observations of children on streets and completed surveys that assessed their own personal growth as a result of their experiences as Play Captains. Results suggest considerable social interaction and use of learning language among children on the Play Streets where Play Captains ran playful learning activities and significant increases in Play Captains’ self-confidence and understanding the benefits of playful learning. We discuss key lessons learned that can help to inform future university-community playful learning collaborations.