Each fall and spring, the author asks his students to dérive, to engage in the Situationist practice of “drift” — a short definition might be to wander on foot without itinerary. The dérive is introduced as the third research method in a series that explores social meanings within built environments. This essay reflects on five years of assigning the dérive and parses students' reactions to and representations of that experience. The author contextualizes the dérive as a critique of postwar urban planning and as a distinct form of walking as urban experience. Finally, he speculates on the possibilities of the dérive as a tool for urban research. “Drifting” is hard to do because it requires active disorientation, an untethering from what grounds us. Yet there is utility in this endeavor — to awaken our senses, but also to disturb received sociospatial relationships and to inscribe new and broader terrains of urban inclusivity.