Various life challenges, such as widowhood, poor health, or significant caregiving responsibilities, can make the possibility of how to spend one’s time in retirement seem daunting. Planning can help people feel more confident and prepared. In this paper, we review research that has examined: (1) life factors impacting fears about and adjustment to retirement, (2) access to resources and utilization of strategies that impact adaptation processes, and (3) the ways leisure and leisure education may be resources to support not only individual adaptation but practices of public health service providers in assisting people who may be struggling with this transition. The review ends with recommendations for public health practice including: (1) the inclusion of leisure and leisure education as a focus of service provision; (2) the development of partnerships or collaborations between public health and recreation-related organizations; and (3) the development and delivery of group- and individual-based leisure education programs.