Purpose: To explore experiences of youth and their parents who responded to a leveraging initiative tied to a sport event. We examined participants’ motivations, experiences engaging with the initiative, and continued involvement with a new sport. Research methods: Five parent–child pairs (n = 10) who participated in the event leveraging initiative (of a total of 35) agreed to participate in semi-structured interviews about their experiences with trying a new sport opportunity. Results and Findings: The initiative seemed relatively effective at encouraging youth to try a new sport but was lacking in terms of fostering continued participation in the sport. Drawing from the transtheoretical model of behavior change, our study revealed that to facilitate continued participation after initial engagement with a leveraging initiative; strategies, support, and resources should be dedicated to the program from the outset.