Adult day programs (ADPs) provide community-based supervised recreational services to older adults living with chronic conditions and their caregivers. Most ADPs continued operating during the pandemic, tasking directors with the responsibility of managing the complexities of the coronavirus disease (COVID-19) pandemic. This study explored how ADP directors managed and experienced the COVID-19 pandemic. Semi-structured interviews were conducted with 18 ADP directors from a large health care region in Ontario. Thematic analysis resulted in four themes that detailed how participants: 1) responded to the pandemic with adapted services; 2) navigated the pandemic responses within systems and organizations, and with each other, clients, and caregivers; 3) felt personally during the pandemic; and 4) gained new insights on their clients and the importance of ADPs in the health care system due to the pandemic. Findings highlight pre-existing and emerging gaps and opportunities within ADP service provision for clients and caregivers, as well as service providers and directors.