Land use is paramount to sustainable development, and in the past, important changes happened under the influence of various factors. Revealing these changes in a meaningful manner, not just as total statistics but also as fluxes and at a spatial level, allows us to detect and associate them with the factors involved. We show a study case in Iași County, Romania, using a raster approach to change detection for a land-use-type database that extends to the 1920s. The database was created from topographic, remote sensing, and field data collected between 1920 and 2006, with five intervals between 1960, 1980, 1990, and 2000, starting from CORINE Land Cover data. These periods mark the socio-political and natural changes in the study area. The change detection results are well matched with the identified drivers and their spatial distribution. The fluctuations between land-use types provide a good way to create drivers’ associations. Our analysis can be easily applied to any other concerned areas and could be used as base references for any legislative intention to determine land-use-type changes because it can be learned from past conversions with regard to failures or examples of good practice.