The labyrinth is an ancient form that has captured human imagination for millennia. Meditative labyrinth-walking is a widespread and growing phenomenon. In this presentation we will explore contemporary meditative labyrinth-walking practices as derivatives of Christian mythology and as activity of mindfulness meditation before looking past the contemporary paradigm to explore an earlier mythological exemplar for meditative labyrinth-walking—the myth of Theseus and the Minotaur. The exploration requires examining the history of the labyrinth as well as the historical events that frame the myth. The presentation culminates in a discussion of a theoretical labyrinth meditation based on Theseus’s labyrinth experience.