The Parent Involvement component of Head Start has multiple goals that include supporting parents' personal development and promoting positive parenting experiences. However, little is known about how experiences such as social support and family leisure may be related to parental functioning, including psychological well-being and parenting stress. In this study of 103 Head Start parents, various aspects of positive parental functioning were related to increases in overall leisure time and leisure time spent with spouse for both mothers and fathers, to increase in leisure time with extended family for mothers, and to increase in leisure time with children for fathers. In addition, increase in social support, particularly informal social support, was related to positive parental functioning for fathers. These results suggest that opportunities for specific contexts of leisure and types of social support may have potential for promoting positive parenting and psychological well-being among Head Start parents.