Developing new structural materials, such as composite materials, has provided many opportunities in bridge engineering. Among these materials, glass-fiber-reinforced polymers (GFRPs), in particular, have found applications in footbridges. However, some of the commonly recognized advantages of GFRPs, such as the high values of the strength/weight ratio, can also be considered disadvantageous for certain realizations, particularly when the composite material used in a footbridge is, for example, subjected to dynamic actions such as those that are induced by wind and walking and/or running users. The induced accelerations can reach high values in comparison to recommended thresholds. Further, the natural frequency decays during the service life, reducing the capacity of the frequencies to move toward the frequency content of the pedestrian step. In this framework, the presented research is devoted to the dynamic comfort assessment of a pioneering cable-stayed GFRP pedestrian bridge, Aberfeldy, which was assembled in 1992 in the eponymous small town, which is located in Scotland (UK). The assessment was numerically performed through a finite element (FE) model, which was tuned based on the literature data concerning geometry, structural details, and in situ-acquired frequencies. The analyses carried out in this study include the evaluation of the accelerations’ time histories, which were induced when simulating a set of pedestrian path scenarios, and the dynamic actions that occur during pedestrian traveling. Specifically, different values of velocity and step frequency were considered as well as the inclusion of walking and running movements. Then, based on the acceleration values, the assessments of comfort criteria for the current standards were elaborated while also recognizing that the peak accelerations—usually attained for short periods—cannot be the only parameters considered in evaluating the pedestrian bridge capacity. This investigation allowed a dynamic comfort rating to be established for the Aberfeldy footbridge.