This paper is concerned with the vibrational comfort evaluation of the cyclist when cycling a rough surface. Outdoor comfort tests have so far only been done through instrumenting the bicycle with accelerometers. This work instruments a racing bicycle with custom-made contact force sensors and velocity sensors to acquire human comfort through the absorbed power method. Comfort evaluation is assessed at the hand–arm and seat interface of the cyclist with the bicycle. By means of careful finite-element analysis for designing the force gauges at the handlebar and the seat combined with precise calibration of both force and velocity sensors, all sensors have proven to work properly. Initial field tests are focused on the proper functioning of the designed sensors and their suitability for vibration comfort measurements. Tests on a cobblestone road reveal that the outcome of the absorbed power values is within the same range as those from laboratory tests found in the literature. This sensor design approach for outdoor testing with racing bicycles may give a new interpretation on evaluating the cyclist's comfort since the vibrational load is not only quantified in terms of acceleration but also in terms of force and velocity at the bicycle–cyclist contact points.