Greater engagement with alternative food supply chains is considered a key factor in reducing a range of environmental and social harms associated with the global agri-food system. However, consumer engagement with these supply chains is low, and little research has investigated this issue in the Australian context. This study aimed to identify Australian consumers’ drivers and barriers in procuring food grown locally from alternative grocery retailers. Self-reported primary or co-equal grocery shoppers (n = 325) completed measures of drivers and barriers to shopping for locally produced food (within 200 km) from alternative retailers, as well as current behavioural engagement with such. An exploratory factor analysis revealed four key drivers (Food Shopping as an Expression of Values, Food Shopping as a Socio-Emotional Experience, Avoiding “Unnatural” Food, Protesting the Duopoly) and two key barriers (It’s All Too Hard, Local Food Scepticism). Multiple regression analysis demonstrated that together, these drivers and barriers explained a significant 9% of the variance in the frequency of alternate shopping practices, of which only the barrier It’s All Too Hard accounted for a significant amount of unique variance. Findings point to ways to encourage engagement with sustainable food systems, as well as critical barriers to overcoming disengagement.