Insufficient attention has been given to the influence of context on health-related behaviour change. This article reports on walk-along interviews conducted with 10 leaders of walking groups while leading their groups to investigate the influence of contextual factors on walking behaviours in groups. Data analysis used ideas from thematic analysis and grounded theory, approaching the data inductively. We identified that characteristics of place influenced the type of walking that people do in groups and the processes used by walkers to make sense of their behaviours in the places they walk. This research provides insight into how place influences walking in groups. It also suggests recommendations for co-ordinators and policymakers that could be used to facilitate behaviour change, when designing interventions targeting public health within the community.