Land cover changes in mountainous regions are potential precursors to landslide disasters. However, the effects of past long-term land cover changes on the characteristics of recent landslides remains underexplored. We studied land cover evolution over a 56-year period on Omishima Island in western Japan to examine the spatial relations of landslides in the July 2018 storm event based on rainfall, land cover trajectories, and topography. We generated land cover maps for 1962, 1981, and 2018 by aerial photo interpretation. We also identified 512 new landslides. Based on 47-year precipitation records, we estimated the return periods of 1- to 264-h rainfalls during the storm using the generalised extreme value (GEV) distributions. Return periods showed wide variation when the derived GEV distributions were applied to 1-km grid rainfall distributions. Despite such pronounced spatial variations in rainfall, we did not observe a clear correlation between rainfall intensity and landslide distribution. In contrast, land cover trajectories had a pronounced effect on landslide occurrence. Landslides were more concentrated on slopes that experienced land cover changes after 1962. A comparison of slopes on farmland developed between 1962 and 1981 (mainly citrus orchards) indicated that landslide density and area ratio were significantly lower on slopes that had reverted to forests than on those remaining as farmland. However, the values of the reforested slopes exceeded those of forests and farmlands that remained since before 1962. Our geospatial analysis revealed that even if the field had shifted to forests, the effects of reduced slope stability due to orchard development had remained for at least 37 years. This suggested that the impacts of converting forests to orchards last longer than harvesting in managed plantation forests.