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 locative media in the networked city. We have designed and trialed the transposition of a paper-based mapping methodology of Urban Gallery (made by chora), via locative and situated mobile media, in a GPS-based ‘app’ called Streetscape. In linking mobility, mobile communication and locative media, we situate cultural mapping within an urbanism of the networked city. Digital tools and locative media offer urbanism and studies of the networked city considerable potential to expand and reflect on dynamic, emergent and participative approaches to mapping. These are ones that potentially allow for the development of new cultural practices of explorative mapping that focus on urban textures and complexities of relations rather than enacting top-down traditions of urban planning. The design and use of Streetscape as an experimental urban mapping tool proves promising in terms of exploring mapping procedures and content. Through proactive use of digital affordances designed for the emerging networked city, one can explore cultural mapping tools that allow people to actively engage in and with their urban environments and thus see the city and its many complex features in creative and unexpected ways.