This paper focuses on the back analysis of an ancient, catastrophic rock avalanche located in the small city of Lettopalena (Chieti, Italy). The integrated use of various investigation methods was employed for landslide analysis, including the use of traditional manual surveys and remote sensing (RS) mapping for the identification of geological structures. The outputs of the manual and RS surveys were then utilised to numerically model the landslide using a 2D distinct element method. A series of numerical simulations were undertaken to perform a sensitivity analysis to investigate the uncertainty of discontinuity properties on the slope stability analysis and provide further insight into the landslide failure mechanism. Both numerical modelling and field investigations indicate that the landslide was controlled by translational sliding along a folded bedding plane, with toe removal because of river erosion. This generated daylighting of the bedding plane, creating kinematic freedom for the landslide. The formation of lateral and rear release surfaces was influenced by the orientation of the discrete fracture network. Due to the presence of an anticline, the landslide region was constrained in the middle-lower section of the slope, where the higher inclination of the bedding plane was detected. The landslide is characterized by a step-path slip surface at the toe of the slope, which was observed both in the modelling and the field. This paper highlights the combined use of a geological model and numerical modelling to provide an improved understanding of the origin and development of rock avalanches under the influence of river erosion, anticline structures, and related faults and fractures.