Abstract: Settler colonial ideology persists not only through official narratives and explicit beliefs but through perception, affect, and the organization of public space. Using case studies of heritage tourism sites in St. Augustine, Florida, I develop the concept of the colonial uncanny: a historically specific, managed affective disturbance that arises when colonial representations reactivate inherited perceptual and affective orientations. I argue that these environments are structured to afford a particular kind of affective encounter with colonial violence for settler visitors. In settler colonial societies, heritage spaces tend to depict the past in ways that do not disrupt settler legitimacy. This often occurs through erasure and silencing, but not always. Settler societies can also manage the past by making violent histories partially visible in representational modes that both disturb and stabilize settler subjects. I call this structure the colonial uncanny. It emerges when historically sedimented ideological residues and surmounted developmental dispositions are reactivated together, so that colonial ways of seeing momentarily reappear as both unsettling and familiar before being restabilized through modes of containment that convert discomfort into education and thrill. Through comparisons of Ripley’s Believe It or Not! Museum, the Fountain of Youth Archaeological Park, and the Old Jail Museum, I show that the colonial uncanny is not an intrinsic property of sites but a relational encounter produced between representational environments and historically positioned spectators. I further argue that this encounter operates through an iterative process of construction and containment, through which unsettling colonial histories are made perceptible, managed, and folded back into everyday forms of settler common sense.