The primary aim of this study was to test whether body mass index (BMI), psychosocial, and behavioral parental variables were associated with similar variables in children at baseline, and whether these variables also served as significant predictors of overweight status in children after two years. While there have been several cross-sectional studies examining the impact of parental behaviors and characteristics on similar variables in children, and several longitudinal studies predicting weight status, BMI percentile, and risk factors of disease in children over time, there is a paucity of research that has identified (cross-sectionally) and then tested (longitudinally) significant parental variables as predictors of weight status in children over time. The current study sought to expand this literature. It was hypothesized that parental variables such as weight, activity level, social support, and eating habits would be associated with BMI percentile, eating attitudes, food selection, energy consumption, and activity level of their children at baseline. These parental and environmental variables were then tested as predictors of the children’s weight status after two years. Cross-sectional results provided partial support for the hypotheses, whereby less active caregivers with higher BMI’s, less social support, and unhealthy dietary habits were associated with heavier children who consumed more calories, reported lower self-esteem, fewer dieting attitudes and behaviors, had a higher preoccupation with food, and consumed more calories from fat. However, the significant cross-sectional parental correlates at baseline were not significant predictors of weight status in children after two years. In order to design more effective environmental interventions, future studies should primarily utilize longitudinal data from all family members to gain further insight into significant relationships between family members’ weight, activity, and health status over time.