The first settlements located on the grounds of Masseria Spina are those from the period of a widespread civilization which lived in dwellings carved into the rocks of Puglia between the ninth and twelfth centuries or so. Those of Massera Spina are among the most important examples in the region.

These settlements are certainly an example of an integrated village, or an integration between religion and work. The rocky settlements arose in the vicinity of "lame" or "mene" (torrential streams) and were generally made up of a complex of caves, each with its own unique qualities. Often, over the centuries, the functions and the uses were modified at the expense of the places used for worship and that, originally, were decorated with murals depicting religious images. The cave complex has undergone several changes since people began living elsewhere, building, for example, a fortified farmhouse around the 15thcentury, made up of two tower-farmhouses, two churches, and premises used in the past for agricultural purposes and oil processing. These rooms are built around an inner courtyard, thus assuming the appearance of self-sufficient village which is quite considerable from an architectural point of view. Between one rupestrian settlement, the Church Minore and the more recent Church of the Immaculate Conception, one can still see traces of ancient piling holes from Neolithic huts and a small necropolis dating back to the early Middle Ages, which at that time had to be quite large.