This dissertation investigates the role of annotative locative media in mediating experiences of place. The overarching impetus motivating this research is the need to bring to bear the theoretical and substantive concerns of cultural landscape studies on the development of a methodological framework for interrogating the ways in which annotative locative media reconfigure experiences of urban landscapes. I take as my empirical cases i) Google Maps with its associated Street View and locational placemark interface, and ii) Layar, an augmented reality platform combining digital mapping and real-time locational augmentation. In the spirit of landscape studies’ longstanding and renewed interest in what may be termed “ordinary” residential landscapes, and reflecting the increasing imbrication of locative media technologies in everyday lives, the empirical research is based in Kenwick, a middleclass, urban residential neighborhood in Lexington, Kentucky. Overall, I present an argument about the need to consider the digital, code (i.e. software), and specifically locative media, in the intellectual context of critical geographies in general and cultural landscape studies in particular.