Utilizing the event travel career concept, this study examined the trajectory of active sport event travel careers through stages of development and the corresponding factors and dimensions perceived to influence career progression in the sport of cycling. In-depth semi-structured interviews were conducted with N=12 amateur cyclists engaged in lifestyles based on active event travel. A grounded theory approach revealed active event travel careers evolve through a complex progression of nine core themes and related subthemes. The core themes included the first event, starting out, motivation, temporal, travel style, destination criteria, event types, spatial, and later in life. Based on these findings a six-stage Active Sport Event Travel Career model is proposed consisting of: initiation, introduction, expansion, peak threshold, maintenance, and maturity. From this model, theoretical contributions, suggestions for future research, and practical implications for sport tourism and event management are discussed.