This chapter examines the use of digital annotations of physical urban space to tell the stories of places, with the focus on situated digital archival material. It does so by introducing and analyzing two different cases in East London that make use of local digital archival content. The first one is a mobile and trail-based experience in Whitechapel that uses Augmented Reality technology. The second one involves a fixed physical memorial in Bethnal Green, where the technology in use is a digital large projection. In the chapter, we critically discuss, through those two very different modes of mediation of archival content and how they related to each of the locations, the implications of linking local context to the design, curation, and the combination of digital archival material with the urban local infrastructure. We suggest that by taking into account the location and its social and spatial context, when designing for hyperlocal to tell stories that happened in these locations in the past, we trigger agency to seek and reveal local stories in situ that make engagement tangible and connect people to places.