There has been little consideration of the role of our relationship with the land in transformative learning. This has been touched on in some discussions of transformative learning (TL) and pilgrimage, and in recent discussions of transformative pilgrimage learning (TPL), but not yet teased out. We think of transformative pilgrimage learning as full of possibilities for fostering reconnection with the natural world and with our deeper selves, toward forming a true connection with the greater web of life that can support our dreaming into existence new healthy communities and a future world. We discuss the background related to TPL while emphasizing threads that tie to an ecological systems perspective, that is, human organisms embedded in a more than human world, and do so in light of our experiences and research on making pilgrimage and living life as pilgrimage. We compare TPL to a new human development framework and its concept of Eco-Awakening, then make theoretical links to embodied learning and altered states of consciousness. We discuss how living life as pilgrimage is embedded in and includes connection to the natural processes of the world, and explore thoughts about how our TPL and our legacy are intimately connected with nature.