For most urban dwellers in the UK walking, whether recreational or pragmatic, has become a peripheral activity. This has major implications not only for public health, but also places increasing environmental and infrastructural pressure on the contemporary city. While any response must be multi-pronged, it would seem that design and technology can make a significant contribution to the promotion of walking in daily life. Taking such a position, the present article describes recent work undertaken as part of a doctoral study, wherein focus has been directed to the visual design of GPS-enabled interfaces for urban recreational walkers. The article begins by setting out the theoretical underpinning of the research. From this, a number of significant early findings from a programme of semi-structured interviews with urban recreational walkers are offered. Here, participants’ reported use of GPS-enabled interfaces is examined, with emphasis being placed on the negative aspects of their technological experience. As it is not yet possible to draw specific conclusions, the author ends by moving to speculate on possible appropriate design directions, which may be pursued in future work.