This chapter contributes to the theoretical discussion on sustainability transitions from oil-based to post-oil society by focusing on the democratic process that accompanies such transitions, especially in urban areas that are exposed to industrial risk. Such industrial risk landscapes are characterized by socio-ecological transformations that unfold gradually over time and are dispersed across space. As emblematic observation and action sites, industrial risk landscapes prompt inquiry into how the toxic legacies of the past can evolve into heritage and opportunities for the future. I maintain that researchers should reverse their gaze in a methodological and epistemological sense to obtain a deeper comprehension of the tangible and intangible, human and more-than-human legacies, while also opening spaces for “decolonizing the imaginaries.” To illustrate these concepts, I present heuristic reflections derived from a series of experimental community-based experiences in Gela, one of Europe’s historical and most significant petrochemical towns. Suffocated by the legacy of its history, Gela seems like a “town without a future beyond oil.” Despite the greenwashing rhetoric promoting the conversion of the plant into a biorefinery, Gela currently grapples with a chronic lack of alternative perspectives. By drawing from urban planning, critical heritage studies, environmental justice studies, and community-based research, I argue that community-based initiatives, such as collaborative mapping, are a powerful tool for unveiling the effects of years of pollution but also for triggering conversations about new ways for things to develop. In particular, the chapter emphasizes that mapping toxic legacies collaboratively delivers counter-cartographies of territories while also serving as a starting point to envision an after-oil future. To explore these themes and the case study, the chapter is organized as follows: The first section introduces the concept of industrial risk landscapes as relevant to the after-oil discourse; the second section links the debate on just urban transitions to “after-oil” visions, highlighting the potential of community involvement in industrial risk landscapes; the third section regards the case study, including the applied methodology; the fourth section is dedicated to the discussion of the collected data; then some final remarks are presented.