This paper discusses the evolution of human settlement in ancient Macedonia from the Neolithic to the Late Roman periods, based on the results of a new multi-disciplinary and multi-scale archaeological survey in northern Grevena (NW Greece). Building upon an unpublished (legacy) survey, we developed a GIS-structured workflow that integrates site-revisiting and surveying strategies (material collection and test pits) with multi-temporal remote-sensing analyses, offering analytical information about site distribution, characterisation, dating, and taphonomy. Notably, the new study led to a 64% increase in the number of known sites. The combined results indicate that prehistory is less represented in the surface record than historical periods, likely due to the impact of soil erosion episodes. The Late Bronze Age and Early Iron Age saw increased site numbers and the emergence of a settlement structure that characterised the area until the Hellenistic period. During the Roman period, the pattern shifted from a seemingly limited use of the landscape towards a model of more extensive habitation. This was driven by the appearance of new rural sites that introduced a land-use regime designed to support agricultural intensification by implementing anti-erosion measures, such as field terraces.