As innovated by French “free runners” David Belle and Sébastien Foucan in the1990s, Parkour is a physical cultural lifestyle of athletic performance focusing on uninterrupted and spectacular gymnastics over, under, around, and through obstacles in urban settings. Through the public practice of Parkour across late modern cities, advocates collectively urge urban pedestrians to reconsider the role of athleticism in fostering self—other environment connections. This article taps ethnographic data collected on Parkour enthusiasts in Toronto (Canada). For 2 years, the author spent time in the field with “traceurs” (i.e., those who practice Parkour) and conducted open-ended interviews with them regarding their experiences with the movement. In this article, the author explores Parkour as an emerging urban “anarcho-environmental” movement, drawing largely on Heidegger's critique of technology along with Schopenhauer's understanding of the will to interpret the practice of Parkour as a form of urban deconstruction.