This work deals with the longitudinal vibrations of the front fork of a bicycle that may originate under front braking, reporting novel experimental evidence and proposing interpretative models to gain insights into the possible causes. In order to acquire experimental evidence of the phenomenon under study, specific road tests were conducted using four component combinations. A modal analysis was performed to investigate the dynamic properties of the front-end components of the bicycle involved in the vibrations observed on the road and estimate the parameters necessary to populate the lumped-element model, devised with the aim of seeking a set of structural parameters that can reduce the sensitivity of the vehicle to different combinations of brake friction materials.