Garden-based learning, a key component of Farm to School (FTS), continues to grow in popularity as a tool for engaging students in hands-on learning. Recent literature calls for professional development to help educators overcome barriers—including a lack of horticulture skills, curricular connections, and time—that often hinder program success and sustainability. This study sought to understand the role of professional development and its ability to support resilient FTS programs in the classroom. Following participation in a multiday FTS professional development program, seven educators participated in an 11-month photo elicitation study to capture their experience implementing FTS in their classrooms. We find that educators drew on FTS professional development to expand their self-efficacy by successfully implementing what they learned, observing effective models, being affirmed by colleagues and others, and growing their overall confidence to engage in the work. Results also identified persistent barriers that professional development alone cannot reduce.