Utilizing a social worlds perspective, the study examined active-sport-event travel career progression in the sport of cycling. Event travel careers are considered potentially lifelong patterns of travel to participate in events that evolve through stages with distinct behaviors and motivations. Quantitative methods were used to test tenets of an inductively derived model of the active-sport-event travel career for cyclists. An international sample of cyclists were surveyed online; N = 1,452 responded. Using general linear modeling, the results depicted an escalation in motivation related to intellectual, social, mastery competence, giving back, and competition against others with career progression. However, while travel behavior related to preferred events characteristics changed with career progression, preferred characteristics related to destinations and travel style remained relatively stagnant. Implications for destination and event management are discussed.