This study investigates pupils' experiences with learning outside the classroom and discusses how these experiences might contribute to 'deep learning' according to a pragmatist theoretical framework and a situated perspective on knowledge. The data comprise materials from three months of fieldwork with participatory observations and qualitative interviews of pupils from two Norwegian primary schools. The results are interpreted according to John Dewey's two criteria for educative experiences, 'transaction' and 'continuity', and to our operationalisation of deep learning. We argue that learning activities that entail both transaction and continuity can be regarded as facilitating deep learning.