We discuss an experimental pilot study collecting and sharing media to explore active citizen engagement with older adults in the city. Our purpose was to inquire into the potential role of audio-visual media collection and presentation to inform urban planning. We encouraged collective documentation of the associations older people have with place and reflected on shared experiences within the context of mobile and civic technologies. We report on different phases of the study, contributing insights on the potential role of digital media to raise awareness and sensitivities to alternative perspectives providing expression of people's values. We speculate on potential opportunities for media architecture to present and re-mix media and make place-based contentions palpable.