This case study examines young children’s access to fresh local produce in childcare settings in rural Appalachia. In-depth, semi-structured interviews with childcare center directors participating in farm to early care and education programming were conducted in the spring of 2023. Centering the perspective of childcare directors, this research explores why farm to school programming is difficult to implement. It specifically addresses the barriers preventing early childcare centers from providing access to fresh and local produce to enrolled children. Eight primary obstacles to implementing farm to early care and education programming were identified: lack of staff; too wide a variety of tasks for directors; the “extra” work that fresh produce requires; lack of knowledge about how to grow food; lack of required kitchen equipment; need for additional funding; unclear or out-of-date regulations about food safety; and a lack of parental time. Limitations of the research include the specific geographic location of the study and the long-lasting implications of the COVID-19 pandemic. Recommendations drawn from this case study include improving communication between childcare centers and regulatory agencies; creative use of alternative gardening practices; participating in a regional food hub; and improved funding.