In contrast to river floods, the enormous erosion potential in catchments contributes significantly to the extent of damage to infrastructure in valleys. This paper investigates the impact of the heavy precipitation event of 14–15 July 2021 on the railroad in the Ahr valley in Rhineland-Palatinate, Germany. In a first step, a detailed overview of the climatological and hydrological drivers using spatially high-resolved precipitation distribution and peak discharge modeling is provided, and the event is placed in a broader context by comparing it to past flash flood events from 1910 and 2016. In a second step, a detailed mapping of damages along the railroad line is performed using aerial photographs. The mapping revealed that bridges are the weakest point during a flood event and that they contribute to an increase and modification of the flood wave through backwater effects. Since flood events are expected to increase in the future, there is an urgent need to increase the resilience of transportation to this hazard and to answer the question of what magnitudes and return periods of events should be used in future sizing of rail infrastructure.