Research examining factors that predict youth’s involvement in organized activities is very limited, despite associations with positive outcomes. Using data from 1043 youth (49% female; 46.4% Hispanic, 35.4% African American, 14.0% Caucasian, and 4.2% other) from the Project on Human Development in Chicago Neighborhoods, this study examined how characteristics of parents (supervision, warmth) and neighborhoods (perceived neighborhood safety and collective efficacy) predict patterns of adolescents’ involvement in organized activities concurrently (i.e., intensity) and longitudinally (i.e., type and breadth). Parental supervision predicted adolescents’ participation in organized activities across multiple waves. Neighborhood violence was positively associated with concurrent participation in organized activities after controlling for socioeconomic status (SES), whereas higher neighborhood collective efficacy predicted greater breadth in organized activity participation across time. These findings have important implications regarding how to attract and sustain organized activity participation for low-income, urban youth.