Background: Few clinic-based food insecurity interventions address transportation barriers to utilizing food resources. Objectives: We assessed the feasibility of using free rideshare-based transportation to reduce barriers to participating in an ongoing clinic-based food insecurity intervention. Methods: Our multi-methods pilot study used patient surveys (n = 155), focus groups with clinic and program staff (n = 10), and rideshare usage data. Results: Of the 95 (61.2%) survey respondents who reported transportation barriers, only 34 (21.9%) used rideshare. More than 80% of rideshare users rated their experience as good or excellent. Clinic and program staff reported that the service allowed patients a greater sense of control over their time and health and emphasized the need for staffing and program-level infrastructure. Conclusions: Free rideshare may address transportation barriers for some patients but multiple options for support and adjustments to how we offer transportation solutions are needed to successfully meet the needs of all program participants experiencing transportation barriers.