Contemporary food systems face several paradoxes regarding equity and sustainability. Considering food production—an issue that simultaneously affects both the supply (production) and demand (consumption) sides—several cities have begun to implement new strategies, called Urban Food Policies. These approaches aim to address the various challenges presented by food system failures, while also involving the existing network of grassroot initiatives. For this reason, these have established Food Policy Councils, arenas where institutions can engage with supply chain actors and food activists, deciding through the processes of participatory democracy their Urban Food Strategies. This article investigates the evolution of a new Urban Food Strategy in a middle-sized Italian town, Trento. Despite a growing number of case studies discussing the promises and problematic aspects of UFS, empirical research and analysis tend to overlook the role of the context in which these processes are embedded and how the system of political, economic, cultural, and environmental opportunities weigh upon the success of these policies. The paper draws upon a multi-method qualitative approach combining in-depth interviews, document analysis, and direct observations of the construction process of an Urban Food Strategy for the city of Trento.