The riding comfort of cyclists related to roughness and unevenness of cycle path surfaces has unfortunately not been given enough attention in the indices used to predict cyclists’ perceptions of roadway environments. This is partly due to the lack of condition assessment methods specifically adapted to the speed and space limits on cycle paths, and a need for developing metrics that describe the perceived comfort of cyclists rather than that of car users. In this paper a novel method, the Bicycle Measurement Trailer (BMT), is proposed to bridge this gap. Eight different surface types, ranging from gravel and different sized concrete block pavements to asphalt concrete in different conditions, have been assessed with regards to roughness. Four of these surfaces were also used for the assessment of their longitudinal evenness. The accuracy and repeatability of the BMT were evaluated. Finally, five different metrics (Dynamic Comfort Index, Evenness Coefficient, 0.5 m Straight Edge, International Roughness Index and Root Mean Square), were calculated from the collected data and assessed. The main findings suggest that the BMT has a high accuracy at normal and high cycling speeds when compared to the standardized road measuring system, Road Surface Tester, and a high level of repeatability at normal cycling speed. The surfaces could be ranked according to their roughness, and the longitudinal evenness was successfully analysed from the collected data. In conclusion, the BMT could be a valuable tool to assess the cycle path surface condition in relation to how cyclists perceive the riding comfort.