This thesis has two main parts; the first addresses the nature of freedom as it is experienced in outdoor environments. The second part explores some of the ways in which these experiences can inform learning and outdoor education. Recollections of freedom were gathered from people who have a professional involvement in the outdoors as writers, photographers, professional adventurers, instructors and teachers. They were chosen because of their deep commitment to sharing their ideas about the outdoors in a variety of ways. Further to that, stories of mountaineering from the New Zealand Alpine Club Journals were read to gather background material on the culture of mountaineering and how the meaning of 'freedom of the hills' has been constructed. The research is based on Peile's (1994) ecological paradigm which has five main themes; holism, complexity, participatory, being and creativity. These themes underpin the ontological and epistemological foundations of the research and also provide the framework for synthesising the experiences of freedom. The research explores the ways that freedom and learning are intertwined and concludes that there are structural difficulties in current outdoor education practices which limit freedom. The research suggests a more ecologically inclusive metaphor for learning based on the Nor 'west storm, as one small step to resolving this dilemma.