The paper deals with the theoretical insight of ruin in the tempo-spatial formation of Chiayi County in Taiwan. The argument of this paper could help urban design discipline in terms of conceptual identification and polemic redefinition. By choosing various sites of Chiayi County, taking photos on these places, looking into historical documentary and consulting with theoretical literature of ruin, the paper tries to explore the possibility of incorporating tempo-spatial references of ruin with design thinking in the context of Chiayi County’s metamorphosis. According to preliminary visiting of ruinous sites in Chiayi, the research divides them into three categories: industrial ruins, ruins in the City Park and countryside ruins. Following this categorization, the study tries to argue that the conception of ruin combines with Genius Loci and Zeitgeist, with a multiple projection of tempo-spatial connotation, which also concerns with the reflection of social and cultural aspects. The study starts with characteristic investigation of various ruinous sites and continues by in-depth interpreting of these landscapes of ruin, as well as a purposeful conclusion on the significance which ruins represent in design thinking and practice.