Experiential education (EE) leads to positive outcomes for K-12 students; however, such practice remains on the periphery of schools. One key to centering EE in classrooms is to do so in teacher education. This study explores what it means to delve into EE as teacher educators alongside our students in field sites far removed from traditional university classrooms. For this self-study, we analyzed instructor journal reflections, research-assistant field notes, and a collective interview transcript. From these, we developed narrative cases of our individual experiences at field sites. Cross-case analysis revealed themes rarely associated with the work of teacher education professors. Like our students, we were confronted in the field with what Christian Itin refers to as physical, social, moral, emotional, intellectual, and spiritual challenges. The shifting realities of our roles as teacher educators revealed what it means to do EE alongside our students. The experience and accompanying reflection prompted us to consider how centering experience in teacher education shifts the oft-directive and didactic nature of our work. To shift their pedagogy, teacher educators must have new images of possibility. Here, we make transparent our journey as teacher education travelers on the path of experiential education.