Physical activity—including outdoor motor play—has been associated with learning and brain-related functions and abilities in elementary school children and adolescence. Few studies have been conducted on the relationships between active play and these cognitive processes in preschool aged children. Several investigations have revealed that adult-directed physical activity can enhance preschoolers’ performance on measures of executive functions, such as inhibitory control or attention. In the present investigation we sought to determine if naturalistic playground play would have a similar effect to adult-guided exercise on a classroom indicator of young children’s cognitive control—on-task behavior during a whole group learning experience. The on-task behavior of 21 three-, four-, and five-year-olds was compared under two conditions—one in which children played outdoors immediately prior to the experience and one in which they did not. Too, the relationship between the level of physical activity on the playground of children and their on-task behavior directly following it was examined. Findings indicate that outdoor play prior to learning resulted in greater on-task behavior for boys and children of low socioeconomic status. Level of activity in play prior to a learning time was positively related to on-task behavior. Implications for scheduling of outdoor play and the role of teachers’ in facilitating more active motor play are discussed. Future research on a larger, more diverse sample of children is recommended. (author abstract)