Social media is now a central communication centre within social worlds bound by particular leisure interests. In the digital age, leisure participants are able to generate and share bespoke, archival content and thus project nuanced messages regarding leisure experiences to their social networks. Adopting an interpretive approach to analyzing multimodal components of cyclists’ Instagram posts tagged with the popular hashtag #fromwhereiride, this study sought to explore meaning embedded within cyclists’ social media discourse. Five overarching themes emerged which suggested through social media, cyclists seek to project nuanced constructions of the self through a range of cultural, embodied, and mobility-related practices. Our analysis shows that social media is a platform through which leisure serves as a late-modern backdrop for social class and gender power struggles. This research contributes original insights regarding the role of social media discourse in leisure whilst providing a foundation for future research.