The cultivation of vines and olives are among the oldest in the Greek land. During the age of Roman rule an extensive cultivation of these plants is observed, whereas the cultivation methods and the production technology both of wine and olive oil is improved. In the medieval period grapes continued to be crushed in grooved and trough like receptacles, a phase occasionally followed by a mechanical pressing of the grape rags. In the sixteenth century the earlier winepress was replaced in many regions by large wooden device, in which the grapes were crushed and their rags were stored until they would be fermented and become appropriate for distillation. In olive oil production the essential technological progress seems to have stopped after the few innovations in the olive oil technology introduced in the years of Roman occupation, when the olive oil production was boosted, in northern Greece in particular. During the Early Christian period the processing of olive crop followed the prevailing practice: a pair of rotating millstones of lentoid cross-section was crushing and pressing the olives, the rags of which were then mechanically compressed. The common terminology of olive oil and wine production used in the literary texts creates problems in the interpretation of the relevant archaeological finds. The barbaric invasions of the sixth and seventh centuries ad seem to have discontinued the olive oil producing activity at least in northern Greece. The reestablishment of systematic olive groves in southern Macedonia seems to be related with the reorganization of monasticism on Mount Athos in the tenth century. A water-driven olive mill of 1324/1325 has been located in Volvi, Thessaloniki, whereas a fully equipped olive oil mill in the Athonite Monastery of Zygos, dating from the sixteenth to seventeenth centuries, has been researched and recorded. It is a characteristic example of the olive oil technology and practice already prevailing in the middle period of Ottoman rule.