Popular media across the Anglosphere has widely feted road cycling as “the new golf,” implying a shift in the social constituency and cultural significance of the activity. Such suggestions posit cycling as a new “middle-class” activity and have also spawned the idea of a new market segment: MAMILS (middle-aged men in lycra). Simultaneously, cycling has increasingly been advocated in health promotion and sustainability discourses, and in urban planning and tourism discussions, and the popularity of cycle racing has heightened. This article explores the cultural meanings of road cycling within this apparently shifting social terrain. Based on interview and participant observations with one road cycling group, it explores the cultural meanings and values of “serious leisure” road cyclists within New Zealand. Observations reveal a midlife, middle-class constituency recasting road cycling in particular ways. That is as a “de-sportified” activity—such that it is loosely structured, noncompetitive, and socially connective. Such revisions adhere to particular middle-class life worlds and aspirations regarding active aging and “responsible” citizenship.