The recent surge in interest in progressive education ideas has often been accompanied by an increased advocacy for learning outdoors, with experiential and holistic learning approaches considered the most beneficial method for cultivating personal and social development and raising awareness of contemporary environmental concerns. However, theoretical and practical unease exists about how increased opportunities to learn outdoors can help young people to reflect on their experiences and make sound decisions. The paper reviews the contribution of John Dewey to debates about experiential education and the development of moral deliberation; as for Dewey there are strong connections between cognition, character and actions. This leads, in conclusion, to analysis of outdoor learning prospects and the extent to which these can benefit personal responsibility and social interaction, and provides learners with the capacity to make dependable voluntary decisions that display stable states of character.