Large, concentrated settlements known as ‘agro-towns’ abound across Southern Italy and other parts of the Mediterranean. The prevalence and persistence of these settlements are very curious but not yet well understood. Initially, scholars interpreted their development as stemming from Southern Italy's economic and social ‘backwardness’ and inequality. This view has now been challenged by scholarship which emphasises that the pre-industrial Mezzogiorno supported not only a dynamic economy but also a diverse array of institutional structures. By recourse to a comparative study within Apulia, this paper suggests that both interpretations are equally correct. ‘Agro-towns’ in Southern Italy were linked to the inequitable distribution of land, perpetuated over the long term, but the institutional origins of this inequality were both diverse and dynamic.