This article explores the use of walking in the artistic practice of contemporary artists Francis Alÿs and Jorge Macchi. The authors propose that these artists use walking and mapping to frame and reframe questions pertaining to social, political, aesthetic, and cultural issues related to structures of power that operate within the city-space. The spatial theories of Henri Lefebvre, Michel de Certeau, and the Situationist International provide a framework for analyzing the notion of space and mobility within the urban landscape. The authors also contend artists' spatial experiences within the urban city-space create encounters that can provide new territories for art and education. To contextualize the pedagogical implication of the proposed research, in the last section of this article the authors discuss ROAM--a mobile game application that expands critical investigations of walking, mapping, and play. ROAM asks players to let go of control, to intentionally "get lost," and to create critical and creative engagement with space.