As social, economic and environmental issues have become more prominent in the 21st century, there has been increased critical scrutiny into the ways that outdoor learning interacts with sustainability issues and concepts. As a result, a number of discourses have emerged which interrogate human/nature relationships in traditional outdoor education and propose greater engagement with place-responsive or sustainable approaches. Drawing on research with teachers in Aotearoa New Zealand, this article explores possible intersections between sustainability education outdoor learning. Accordingly, this article focuses on two key ideas: First, the nexus of experience and place offers significant promise for educational endeavours that seek to educate for a sustainable future. Second, traditional conceptions of wilderness as a pedagogical site, can be problematic for outdoor education programs which seek to claim the ground of sustainability. While there is much that can be gained from journeys in remote pristine environments, not all of these experiences necessarily lead to the development of attitudes, understandings, skills, and motivation to live more sustainably. Furthermore, approaches to outdoor learning that seek to develop connection to and care for remote, pristine places, at the same time ignoring more local or impacted places, could present a dichotomous view of "nature" to students, thereby disrupting efforts to educate for sustainability.