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Youth participation in structured activities is associated with a range of positive outcomes, and program features and degree of participation moderate these effects. However, relationships across dimensions of participation or between program features and participation—both keys to understanding impacts of structured activities—have rarely been addressed. We use hierarchical linear modeling to investigate correlates of youth engagement, specifically belonging and challenge, in a sample of 1141 youth in 119 offerings in 66 sites. Results reveal that intensity positively predicts belonging and to a lesser extent challenge; however, duration is negatively associated with both aspects of engagement. Staff practices of providing a welcoming atmosphere and leadership opportunities predict belonging; while provision of skill-building predicts challenge.