The study explored connections between play and psychosocial development across Chickering and Reisser’s (1993) vectors in a college student population to test the inference that play may relate to development. Scores on the Caillois Play Dimensions Survey (CPDS), which measures self-reported play behaviors using modifications of Caillois’ categories of play, were compared to task and scale scores on the Student Development Task and Lifestyle Assessment (SDTLA), which measures progress across Chickering and Reisser’s (1993) developmental vectors. Participants included 42 male and 39 female college sophomores who attend schools in the Mid-Hudson Valley of New York. Multiple regression analysis of CPDS total scores and SDTLA summary scores showed a positive correlation at the p = .005 level. Each CPDS dimension was analyzed in relation to the three SDTLA task and one scale scores. In the resulting 20 partial correlations, 3 of 20 were statistically significant. The Establishing and Clarifying Purpose scale was positively correlated with both the Competitive Play – Mental scale (p = .004) and the Imagining, Imitation and Play-Acting Games scale (p = .02). In addition, the Mature Interpersonal Relationships scale was positively correlated with the Competitive Play – Physical (p = .02). These findings supported the hypothesis that involvement and participation in play activities positively relates to psychosocial development.