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As part of wider engagement with different ways of being mobile in the city, human geographers (like many others) have critically engaged with the possibilities and prospects of walking as a way of attending to the city. For human geographers, walking is particularly interesting because it has formed the basis for a range of historical and contemporary fieldwork activities. This paper outlines the possibilities of enhancing the ways in which a walking-based field-work can help cultivate techniques of critical engagement with urban life. Our discussion is drawn from the experience of teaching on an undergraduate field-course in Berlin. We reflect upon the ways in which the walking-based activities of this course were enhanced by the provision of simple digital technologies. Our discussion focuses on two issues. First, we argue that these technologies not only provide ways of capturing images of the city: they also enhance the affective element of student engagement with the city, providing the basis for the further cultivation of cognitive and critical activities. Then, and second, we discuss how, upon returning to Southampton, these technologies allowed students to produce web-based virtual pathways through which to move and engage with the details and rhythms of city-space. Such activities, we argue, have the potential to become part of wider pedagogical efforts to cultivate cultures of walking in the city.