Traditionally a medium for social connectedness between parents and their children, playgroups have been reimagined to include older people. Intergenerational playgroups (IGPs) bring together participants that span across generations, facilitating interactions that promote self-esteem for older people and trans-generational learning for children. In response to challenges to well-being from social isolation experienced by elders, and exacerbated by the COVID-19 pandemic, a virtual IGP was initiated by a playgroup organization, intended to harness technology to facilitate interactions between preschool-aged children, parents, and residents of aged-care facilities. This paper evaluates a virtual IGP program via the review of program development, implementation, and related wellbeing outcomes. The paper provides recommendations through a framework to enhance the planning and execution of future virtual IGPs.