This study investigates how changes in cycling encouragement program game mechanics affect measured bicycle riding frequency. The study relies on cycling program participant data from three large-scale and recurring annual encouragement campaigns (the UK National Cycle Challenge, Sydney Rides Challenge, and Atlanta Bike Challenge) with a total of 66,762 unique registrants. We compare effects for users both engaged via smartphone applications and across sub-samples determined by the participants’ reported riding activity at program sign-up. Comparing year-over-year differences for each program (including pre- and post-introduction controls) indicates that adjustments in progress indicators (points) and a greater emphasis on smartphone application connectivity are effective at generating greater reported riding activity. Based on this we confirm that digital encouragement and/or gamification campaigns may, if structured and managed correctly and given sufficient support and resources, offer the potential for communities to generate additional ridership and interest in bicycling while also collecting data useful to improving infrastructure planning and design decisions. Finally, we identify significant differences of scale between the impact of these changes between participants tracking via smartphone applications vs. those relying on manual entry; this provides evidence in support of the increased attention being paid to personal GPS-enabled devices as a means for better facilitating behavior change.