Mapping is intimately related to the practice of urbanism, one that is beginning to be transformed by social and locative media. This chapter presents research in a project into the design and use of a GPS-based ‘app’ called Streetscape based on the mapping methodology of Urban Gallery (by chora). In linking mobility, mobile communication and locative media, cultural mapping is situated within an urbanism of the networked city. Digital tools and locative media offer urbanism and studies of the networked city considerable potential to reflect on emergent, participative, and explorative approaches to mapping that focus on urban textures and complexities of relations rather than enacting top-down traditions of urban planning. Through proactive use of digital affordances designed for the emerging networked city, one can explore cultural mapping tools that allow people to actively and creatively engage in and with their urban environments.