This work responds to isolating urban places, and contributes new ways for thinking about placemaking. Progressing through autoethnography and prototyping, we critique design proposals with Lefebvre’s theory of utopia. There inhabitants can enjoy and shape their place together without risking depletion of their abilities and motivations to do so. The critique produces political sensibilities that help us make sense of common tensions among inhabitants, landowners, and visitors, and generate possible responses. The critique process itself illustrates how designing through critique with theory can help us think in new ways. This paper contributes a display of how design with critical theory can happen, ultimately to support our abilities and motivations to envision and make places of social flourishing that can respond to our socio-environmental crises.