This article advocates a holistic approach to education concerning literacy and ecological literacy development and builds on data from two different case studies in compulsory school classes in Sweden. The study is built on action-based research and the data material was analysed through directed qualitative content analysis. We argue that place is an aspect of pedagogical settings that needs more consideration in teaching practices, and that various features of education, such as language, meaning-making, literacy development of various kinds, and identity building, are intertwined with place. The results of this study show that interactions between students and direct encountering with two outdoor places are connected with student agency, emancipation and empowerment. The learning opportunities enabled in these two pedagogical settings were, at least in part, due to the teachers' non-prescriptive directions and an "outside-the-box" way of thinking. Such approaches supported and empowered students and allowed them develop critical thinking on their own terms.