Anti‐automobile, anti‐capitalist, and pro‐environmental worldviews are known to shape bicyclists’ right to the city demands. This research uncovers another layer of their radical engagement with the city: playful enjoyment of architectural structures and urban space, using the case study of Midnight Mystery Ride, a community bicycle ride taking place in the middle of the night once a month in several cities around the world. Through theoretical lenses of play and rhythmanalysis, I argue that bicyclists at night take over spaces built with exchange vale in mind and introduce use value in the same spaces. Interviews with bicyclists demonstrate how their unconventional use of space questions separation from natural rhythms and nature. I demonstrate that their nighttime use of the city is also a critique of how urban space is organised largely for profit and discipline and of how the human and playful potential of urban space are not fully realised.