Applying latent class and regression techniques to data from the NICHD Study of Early Child Care and Youth Development (n = 997), this study explored the potential academic advantages of time spent in out-of-school activities. Of particular interest was how these potential advantages played out in relation to the timing and duration of activity participation and the family contexts in which it occurred. Participation closer to the start of high school-including consistent participants and latecomers-was associated with higher grades at the transition into high school, especially for youth from low-income families. Sensitivity analyses indicated that this link between school-age activity participation and adolescent academic progress was unlikely to be solely a function of selection. It also tended to be more pronounced among youth from lower-income families, although without varying by other aspects of family status or process.