Agricultural land abandonment is a globally significant threat to the sustenance of economic, ecological, and social balance. Although the driving forces behind it can be multifold and versatile, rural depopulation and urbanization are significant contributors to agricultural land abandonment. In our chosen case study, focusing on two locations, Ruen and Stamboliyski, within the Plovdiv region of Bulgaria, we use aerial photographs and satellite imagery dating from the 1950s until 1980, in connection with official population census data, to assess the magnitude of agricultural abandonment for the first time from a remote sensing perspective. We use multi-modal data obtained from historical aerial and satellite images to accurately identify Land Use Land Cover changes. We suggest using the rubber sheeting method for the geometric correction of multi-modal data obtained from aerial photos and Key Hole missions. Our approach helps with precise sub-pixel alignment of related datasets. We implemented an iterative object-based classification approach to accurately map LULC distribution and quantify spatio-temporal changes from historical panchromatic images, which could be applied to similar images of different geographical regions.