Adolescence is a period of rapid developmental changes. Only in the early years of childhood do individuals experience such a brisk pace of change. However, all too often, out-of-school time (OST) programs do not recognize how quickly the needs and interests of adolescents shift along with their developmental changes. Program staff know--and studies have documented--that, as children enter adolescence, their participation in OST programs drops off (American Youth Policy Forum, 2006; Lauver, Little, & Weiss, 2004; Sipe, Ma, & Gambone, 1998). To attract older youth, programs need to offer experiences for teens that look and feel different from those designed for elementary school children. This article, drawing on data collected in a larger study of practices that engage older youth in OST programs over time (Deschenes et al., 2010), shares insights about programs that successfully engage older youth and the strategies they use to maintain high participation rates. In the study described herein, attention to developmental differences emerged as central to the strategies that kept middle and high school youth engaged in OST programs over time. This article sheds light on how a set of school and community-based programs with high rates of participation addressed these changing needs. First, an overview of the larger study and description of the characteristics of the program sample are presented. Then, some of the findings that indicated the importance of addressing developmental differences as a participation strategy are detailed.