This research focuses on the territories of Meridional Apulia in the Middle Ages. A diachronic inquiry was carried out on the transformation of agrarian landscapes in a 401 km² zone, East of Taranto, encompassing at the same time the fields, the agrarian margins and settlement vestiges. Among other things, digs have accounted for the archaeological value of tall, drystone walls (paretoni) as sedimentary contexts and territory markers. The emergence of an economic basin centred on Manduria appeared from the 5th century B.C.E. From that time on, the nature of the substratum has been orienting the settlement location and the agricultural choices, though different settlement patterns and agrarian systems have been replacing each other since then. Thus, Taranto and Brindisi oriented the distribution of space towards the openings linked to the world-economy specific to the Late Antique period. Later, in the 8th century, the changes affecting the road network illustrated the central role played by Oria, which became a strategic pole in Longobardian Apulia, in terms of resource draining. At the same time, the city ruled over the Brindisi plain and demarcated its territorial limits towards Taranto. In the 9th century, together with the Byzantine reconquest, there emerged a dense network of rural settlement; as regards olive production, its expansion has been attested by anthracology. In the Late Middle Ages, while Oria lost its fame, the Mandurian basin fed the fluxes deriving from Taranto and Lecce, which, together with Brindisi, became the new poles of a region that marked the frontier with Latin Europe, at the border of the Muslim and the Byzantine worlds. Towards the end of the period, successive social changes led to the predominance of latifondo and agro-town model.