Gravel, a cycling discipline practiced primarily on unpaved, remote roads, has seen a surge in popularity in recent years. Accompanying this growth have been fervent debates about what gravel cycling is and how to define it. However, no research has yet been done to describe this discipline and its meanings to society and individuals. Thus, this case study aimed to understand individuals’ experiences and motivations for gravel participation. Through interviews and a reflexive thematic analysis, three themes were crafted: (1) gravel cycling encourages and provides a sense of freedom, (2) embracing the unknown: participants experience physical, mental, and emotional development through gravel cycling, and (3) gravel cycling provides connection through the convergence of self, community, and nature. We provide conclusions regarding gravel’s significance in light of current trends in adult sport participation and present practical implications for cycling event organizers, grassroots sport organizations, and the adult sport and leisure communities.