Heidegger’s three Country Path Conversations have generated much scholarly interest for their elaboration on Heidegger’s thinking of Gelassenheit, scientific and technological thinking, the work of art, evil, and the political aftermath of World War II. In this paper, I argue that these texts also, upon closer analysis, contain a Heideggerian pedagogical philosophy. In each text, I will show, a dynamic of teaching and learning is at play, most especially when it seems to be absent. Further, I will show how only when these three texts are read together does a fuller account of Heidegger’s pedagogy emerge. In the “Triadic Conversation,” I draw out the affective dimensions according to which the Guide’s teaches the Scientist to contest his own worldview. In the “Tower Conversation,” I show how the Teacher must practice what he himself teaches, choosing to tarry with that which causes him discomfort and anxiety. Finally, I read the “Evening Conversation” as an example of students assuming the teaching role themselves when the teacher is nowhere to be found, fulfilling the hopes any teacher would have for her students.