In the wake of the Milan Urban Food Policy Pact, cities around the world have been taking the lead in designing their own City Region Food System (CRFS). A City Region Food System aims to foster the development of resilient and sustainable food systems which encompass an urban centre, a peri-urban ring, and the rural areas surrounding a city. This chapter argues that a CRFS must also focus on nature and the context it provides rather than on the social and environmental indicators typically used to describe a city and its context. This includes the nature context of the rural-urban region where a city is located. A CRFS needs to include a wide range of food system actors including those who give expression to the nature context of the region. It must also focus on cooperation, decision-making, learning, and distributive leadership among the various CRFS actors. We discuss examples of emerging CRFSs from Amsterdam, Rotterdam and Washington DC to illustrate these principles.