The aim of this research is to investigate the role of smallholder farming in tackling food security and sustainability related challenges in the developed world. In this regard, the relevant literature is discussed and a System Dynamics modelling framework that captures self-sufficiency of cereals produced in the United Kingdom, as an indicator of national food security, is developed. The simulation results from a scenario analysis indicate that appropriate governance and effective policy-making interventions, supporting smallholding farming and short food supply chains in the developed world, provide promising grounds towards ensuring food security and social cohesion, while further promoting economic growth and environmental sustainability. Finally, this research is an initial approach towards the development of food security early warning systems and decision support tools that could be employed by policy-makers and regulators to design effective interventions for the sustainable development of food supply systems.