When busy urban areas are pedestrianised, the relationship these places have with those using them changes. Most obvious is the topographical increase in the availability of space for those traversing it on foot or bicycle. Nevertheless, there are more subtle changes as well. Regular users of pedestrianised spaces begin to forge routes, habits and responses, shaping the way the (newly) available space is used in practice. In this paper, we describe a project at King's College London which sought to explore this in the context of the newly pedestrianised area of the Strand, one of Central London’s main thoroughfares, which abuts KCL’s campus estate. We used methods drawn from deep mapping combined with quantitative and qualitative observations of research participants' walking experiences. Through GPS traces of their walking routes and qualitative interviews, we focused on understanding the benefits of pedestrianisation, the impact of new street furniture on pedestrian habits, and the transformation of the space into an area for both dwelling and traversing. Such spaces give rise to conceptual and intangible "labyrinths" constructed and mediated through people's individual experiences and through digital locative media. This study demonstrates the potential of the deep mapping paradigm in enhancing our understanding of the pedestrian walking experience in newly pedestrianised areas such as the Strand. We show how deep mapping can support spatial analysis and contribute to developing a comprehensive research and design strategy for urban areas by integrating geospatial technologies and participatory research methods.