The apparent features of a rural landscape are the final result of the interaction among several natural and anthropic factors. The analysis of a landscape, as well as the identification of its best management strategies, can be improved when useful information about its modifications along a wide time period is available, so as to assess the effect of the transformations that have taken place there. The implementation within a geographic information system (GIS) of geographical information derived from ancient historical maps, combined with modern digital cartography and recent remote sensing images may provide a very powerful tool for a better-informed analysis and targeted decision-making strategies about the most appropriate rural landscape planning. With the purpose to detect the land use changes in a typical rural landscape in the Basilicata Region (Southern Italy), spatial analysis using free and open-source GIS tools, in which data covering a period of about two centuries, from 1829 to 2017, were implemented. This multi-temporal analysis was carried out to investigate the landscape structure transformations through the assessment of land use change and the implementation of a methodology for the identification of areas in which there has been a natural evolution of the rural landscape. Then, using landscape metrics and spatial analysis tools, some areas in which the landscape has naturally evolved without any anthropic intervention during these 188 years have been identified, and changes occurred on the rural landscape were assessed quantitatively.