The use of topographic airborne LiDAR data has become an essential part of archaeological prospection, particularly as a tool for detecting archaeological features in the landscape. However, its use for landscape reconstruction and understanding archaeological sites in their environmental context is still underutilised. To this end, we took an innovative approach to using LiDAR data as a means of discovering, documenting, and interpreting agricultural land use systems by looking for significant environmental variation within a microregion. We combined information from LiDAR-derived DEM derivatives with archaeological, geological, and soil data. We introduced two methodological innovations. The first is the modified wetness index, which combines the LiDAR-derived precision with the accuracy of the effective field capacity of the soil to obtain a very realistic predictor of soil quality. The second is the modified landform classification, a combination of topographic position index and visual geomorphological analysis, which amalgamates two of the most important predictive variables for the distribution of plant species. Our approach is demonstrated by a case study focusing on early medieval settlements in the context of agricultural land use in the subalpine microregion of Bled (Slovenia). It revealed that early medieval settlers were drawn to light soils with high water retention capacity. Such soils were particularly suitable for the cultivation of barley, which is known to have been one of the most important staple crops of the period, especially in colder climate such as subalpine. Soils with lower water retention capacity were not colonized until the eleventh century, which may signify the transition at that time to a higher level of agricultural organisation and wheat as a staple cereal food.