The movie "Island Etude" provoked the enthusiasm of Taiwanese people to conduct bicycle tours around the island and also raised peoples' awareness and desire to search for dreams and make them true. This article denotes the author's implications of the cycling sport on a long-term personal experience and observation upon riders' behavior. The paper refers to Gadamer's concept of "playing" to investigate the meaning of the cycling sport. It is found that the process of bicycle riding is non-stop and "interpretative", leading to a different sensation each time. By going through various kinds of road conditions, riders realize the highs and lows of life. Some riders would recognize the meaning of "letting go". The consecutive pedaling exercises bring about inter-subjective combination, to ensure the integration between the body and machine. In the outdoor environment, riders get to appreciate the inter-subjectivity between human and the nature, to reach "man-nature integration" by being refilled with life. At the "moment" of cycling, riders part themselves from materialism, triggering aesthetic experience, as a medium to be "liberal". By "playing", riders abstract themselves from the reality, as a temporary ecstasy to experience total freedom of body and mind. These reports conclude that with comprehensive self-understanding, riders settle down back to the reality with a profound enlightenment.