Parkour and free running are newly emerged high risk urbanised activities still relatively understudied. They don't appear to be subject to rules and regulations with aims and objectives being unclear. There are no distinct signs of competition and yet competitors are extremely trained, highly ordered, thriving on the danger and adrenaline participation produces. The participants perform dangerous gymnastic movements utilising awkward obstacles without the use of protective clothing and don't appear to be concerned with the welfare of people in the vicinity. The activities are associated with self-improvement, endurance, discipline, strength, flexibility and balance. Parkour and free running videos are frequently posted on the self-broadcast website, YouTube. Here participants can be seen leaping from high buildings, climbing walls and jumping between handrails. This study presents the results of a phenomenological study of eight parkour and free running participants. A systematic IPA procedure was incorporated into the study to enter into a participant's reality to obtain experiences of parkour and free running. Through IPA interviews participants describe their experiences of the phenomenon being studied. It was discovered that participation provides emotional, physical and psychological development, health benefits, the development of new skills (e.g., pushing personal boundaries), an increased sense of individuality, an opportunity to acquire status and develop a new personal identity, the generation of personal meaning (philosophy, spirituality and aesthetics) and an increased sense of belonging (distinct group norms, subculturally shared experiences and a unique sense of authenticity). The participants explained that they were initially motivated by thrill seeking, risk, improved health and enjoyment. They asserted that participation provides physical and mental training, a sense of mastery and personal challenge. Regular practise and commitment furnishes a participant with a sense of being in the present and a deepened sense of spirituality and enjoyment. The unique characteristics of parkour and free running (e.g., philosophy, environment, spirituality, perception and aesthetics) are linked to the characteristics of extreme sport which indicates that parkour and free running are part of a counter culture.