This conceptual outline is based on findings from the Creative Food Cycles project with the specific focus to enhance innovative and creative cultural practices between food, architecture, and conviviality in a transnational and European perspective. It refers in a double perspective to the EU Farm to Fork strategy: to embed and extend innovation in Food Cycles into urban contexts and to create benefits for all citizens and actors along Food Cycles and and thus a main stage for circular economy, contributing to a just transition and to enhance urban transformation to sustainability and resilience. The Regenerative City scenario serves to evaluate findings from the creative and cultural activities of the Creative Food Cycles project that have been carried out as design-based research. Circular Design embodies the need of the Regenerative City for the effectiveness and adaptivity of strategies, tools, and processes of change. In particular, the “spatial-digital nature” of Circular Design and the “learning nature” of multiscalar design processes are put forward as accelerators for transformation.