Contemporary discussion frames food security and sustainability as a wicked problem, in that it is multidimensional, hard to define and thus extremely challenging to solve. As such, new models and approaches have evolved in an attempt to address the sustainability of food in line with the Sustainable Development Goals, once such model is that of City–Region Food Systems. One of the challenges of addressing urban food systems is that of linking rural regions with urban ones, often distinguished as spaces of production and consumption. Reimagining peri-urban/rural food spaces would potentially address sustainability challenges by shortening food systems, generating greater transparency and providing greater opportunity for consumer influence. Furthermore, City–Region Food Systems provide an alternative method to increasing food security and sustainability that increased production and intensification of agricultural practices. The challenges and benefits of this new concept are systematically tested through innovative methods within the EU project Urban Rural Gothenburg, which seeks to create new links between the city’s urban and rural spheres, thus making novel contributions to food security, food affordability and food injustice. This paper discusses this cutting-edge concept of City–Region Food Systems as an emerging field of research, using examples from past and ongoing work undertaken by Urban Rural Gothenburg to explore its benefits and challenges.