Heritage planning in Ontario has created a landscape of protected properties that are disassociated with surrounding urban and agricultural development. Waterloo Region is one of the fastest growing municipalities in Ontario and must meet the demands of an increasingly diverse population while maintaining cultural and natural heritage resources. The Region’s protected landscapes represent a narrow view of history, denying the cyclical nature of ecological processes and giving little weight to the violent and exploitative aspects of our past and present society. By acknowledging multiple perspectives of time, there is potential to manage landscapes that engage present and future communities in a meaningful way. This thesis aims to critique the practice of selective and opportunistic preservation of the built form and ecological regions while offering the designed landscape as a catalyst for heritage preservation and urban intensification. The elements of stasis and flux, form and process are integrated into typological site designs across the Region. Located at the intersection of heritage and urban growth districts, the designs create a public territory between the two domains. This third space becomes a safe place for constructive conflict, a stage for rehearsing alternative scenarios, and a new common ground for people with diverse histories.