The purpose of this study was to describe the ways that participation in a leisure organization contributed to the health and wellbeing of middle-aged and older women. We analyzed 1,693 members' responses to a query about meaningful experiences garnered through participation in the Red Hat Society. Results suggested that older women's lives have been enriched and changed by their experiences, with the women in this study citing multiple psychosocial health benefits from their participation in the Red Hat Society. Main themes encapsulating these health benefits were creating happy moments, responding to transitions and negative events, and enhancing the self. These findings are related to research on positive psychology, social support and coping, transformative leisure processes, and social identity formation. We conclude by providing suggestions for applying these findings to leisure and health promotion programming to enhance women's health and well-being in later life.