The “San Michele Arcangelo” historic trail (Aurunci Regional Park, central Italy), located along the southern slope of Mt. Altino, which is highly prone to rockfalls, is hiked every year by thousands of faithful on pilgrimage who are exposed to such kinds of instabilities. To contribute to a better understanding of the condition and evolution of such phenomena, providing a susceptibility scenario able to support the adoption of mitigation measures, a specific analysis was completed based on field and literature data. Three-dimensional virtual outcrop models were obtained through both photogrammetric and iPad Pro LiDAR surveys to derive geomechanical features of outcropping rocks and estimate potential detaching block volume. Possible mechanisms of detachment were then analyzed using the Markland test method. Susceptibility to rockfall propagation and block deposition was analyzed using GIS processing and rockfall propagation simulations based on deterministic/stochastic models. Such models consist of a combination of a deterministic algorithm able to simulate the physics of rockfall movement during propagation and a stochastic treatment of input parameters based on random sampling within defined interval. Two different rockfall simulations were compared in this study using the Rockyfor3D™ (ecorisQ Association) software and the newly developed RocFall3© (RocScience) code. The use of iPad Pro LiDAR survey provides accurate and high-resolution point clouds, with high speed of acquisition and real-time processing of data. Discontinuity sets identified from 3D models have represented the input for kinematic analyses of slopes, allowing to identify potential failure mechanisms among wedge and planar sliding or toppling. Rockfall simulations indicate the potential for rock blocks propagation and deposition over the whole study area. Comparing the results of rockfall simulations with the geomorphological map of the area it is evident the control exerted by the hydrographic network on rockfall propagation as demonstrated by the presence of screes and slope deposits along the main channels. Understanding the potential susceptibility to both propagation and deposition of rock blocks along the trail provides useful indication for the assessment of appropriate mitigation measures to realize for the safer touristic fruition of the site.