Despite progress from scientific and technological advancements, road safety remains a major issue worldwide. Road accident impacts such as fatalities, injuries and property damage consist considerable costs borne not only by involved people but society as well. This study aims to present preliminary findings of in-depth accident analysis for two-wheelers (bicycles and powered two wheelers – PTWs) across six countries in Europe. Data regarding the conditions underlying accident occurrence are presented, including time and date, weather, vehicle and road conditions and rider-related parameters such as age, intoxication and use of protective equipment. In addition, a Two Step Cluster Analysis is implemented in order to explore any possible classification of the analysed cases. It appears that two clusters are formed: the first includes more favourable conditions (“no wind, no drugs, good lighting”) while the second consists of less favourable conditions for road safety (“windy, lighting, unknown DUI condition”). This hints at a meaningful separation of the examination of two-wheeler accidents when the influence of outside factors is considerable. The inclusion of different but representative areas across Europe offers robustness and transferability to the data and respective results.