Intergenerational volunteerism is a global phenomenon that aids multiple generations. Considering the positive evidence of volunteering among older adults and their desire for engagement with children, it is important to explore older adult volunteers' experiences in intergenerational programs with a specific focus on the cultural and social impacts of volunteering in educational settings. Using a phenomenological qualitative approach, 43 interviews with older adult volunteers (23 in South Korea (Korea) and 20 in the United States (US) in intergenerational programs were conducted. Participants were recruited from the Beautiful Story Grandma (BSG) in Korea and the Foster Grandparent Program (FGP) in the US in 2019. Three major themes emerged from the interviews revolving around the role of culture and other demographics in the experience of volunteering: (1) Benefits from volunteering with children that transcend demographic and geographic differences; (2) distinctive cultural factors lead to different experiences of volunteering in educational settings; and (3) operational and procedural differences of volunteer programs impact older adult volunteers' experiences in educational settings. This comparative research can inform the development of culturally responsive intergenerational volunteering programs for older adults and other generations in their communities.