The qualitative data presented in this paper was part of a larger concurrent mixed methods study evaluating the effectiveness of a transportation program (Project TRIP) for low-income residents in rural eastern North Carolina. Twenty stakeholders involved in TRIP were interviewed, including riders (n = 12) of which 83% were over 50 years old, program staff including the program coordinator and 5 case managers (n = 6), and transportation providers (n = 2). Due to the COVID-19 pandemic, interviews were completed by phone with each participant. Themes from the qualitative data included the: (1) Emotional, health, & financial impacts of TRIP, (2) Changes that should be implemented into TRIP when replicating the program, and (3) Unique aspects of how TRIP operates that could inform other rural transportation programs. Thematic analysis was used to analyze the transcript data. The findings are couched in the context of how TRIP potentially defrays the impacts of cumulative disadvantage that residents experience over the life course by increasing access to healthcare.