Although behavioural nudging has been often used as a method to promote sustainable choices, its application is quite limited in the field of active mobility. Gamification and rewarding schemes appeared recently in mobility sector to nudge urban cycling. The scheme presented in this paper was based on a TRL9 antifraud system to certify, monitor, and reward urban bike rides in in 3 different cities during 2022. About 1,500 users were engaged in Braga, Istanbul, and Tallinn, saving more than 133 tons of CO2 in 6 months, and spending more than 85,000 euros in local shops. The paper presents the quantitative (KPIs based) and qualitative (users questionnaires based) assessment as well as the additional data analysis results that were carried out during the scheme testing. The correlation between trip, weather and socio-demographic data provided valuable knowledge that can be used to target vulnerable groups and to enhance the cycling incentives for bad weather days. The knowledge extracted can be integrated into the climate neutral strategies of the transition cities/regions for designing and implementing more efficient future actions and investments to successfully promote greener and more active mobility, ensuring high levels of cycling throughout the year.