This article outlines narratives of trespass. It analyses relations between the personal and the social in abandoned urban physical surroundings. Grounded in our own duo-auto-ethnographic encounters with off-limit places, the research examines the classic notion of liminality through a set of prisms that are less than orthodox. It does so by stressing the formative and transformative possibilities of those threshold spaces that often get bypassed, surpassed or trespassed. Through a series of vignettes describing moments of urban exploration in different parts of Estonia, our implicit aim is to unsettle such conceptual categories as risk and adventure, material decay and transgression. Explicitly, we argue for revisiting storytelling tropes such as the flâneur or the stalker, freeing them up from their respective leisure and pastime associations.