A decline in children's opportunities for outdoor play was observed during the past decades. Expanding opportunities for outdoor play through intergenerational programs for children and elders could benefit their mental and physical health. This study explores the learnings that Canadian grandparents and their 3- to 5-year-old grandchildren attained through intergenerational outdoor play. Semi-structured interviews were conducted with 14 grandparents from British Columbia, Canada. Using thematic analysis, we identified six themes related to what grandchildren learned, two related to what grandparents learned, and one related to what grandparents and grandchildren learned together during outdoor play. Findings from this study indicate that outdoor play provides a unique opportunity to develop skills that are useful at grandparents' and grandchildren's respective life stages and should therefore be supported by educators and other professionals who work with families.