This paper makes use of Aesop’s Fable, the Tortoise and the Hare, to explore how we can facilitate outdoor learning in a way that helps to develop connections with nature. For many, especially young people and those experiencing physical and/or mental ill health, stepping outside into a natural environment can be a real challenge. Some of the themes explored: Potential barriers to participation - when Doing gets in the way of Being in nature; The role of the facilitator in fostering comfort rather than initiating concern (distress); The use of stories within outdoor education to foster familiarity, comfort and connections