In aiming to support school-based outdoor learning opportunities, this paper critiques the extent to which Deweyan and neo-Aristotelian theorising is helpful in highlighting how personal growth and practical wisdom gains can be realised. Such critique is necessary, as there are signs of an implementation gap between practice and policy, which is made worse by a lack of conceptual clarity about how educational aspirations can be dependably achieved. Dewey's habit-forming social constructivist emphasis on learning and problem-solving is reviewed and the prospects of a neo-Aristotelian conception of human flourishing, which recognises that virtues are nurtured as moral sensitivities, are then considered. Concerns that Dewey's writings are often vague on how ideas can be operationalised and criticisms that Aristotle's educational thoughts rather over-privilege cognition relative to emotions are also addressed. The article concludes by teasing out suggestions on how Deweyan and neo-Aristotelian ideas on learning might coherently inform curriculum planning and pedagogical practices.