Background: To reach the promise of age-friendly communities, more complete understandings of how participation in community occupations occurs, in place and over time, is needed.Aim: To explore older Canadian women's engagement in community occupations as it occurs over the lifespan and in context.Materials and methods: Data from three selected participants were drawn from an exploration of older adults' social connectedness in neighbourhoods, which involved an ethnographic approach involving narrative interviews, go-along interviews, and activity tracking and follow-up interviews. A transactional lens oriented analysis, considering occupation in place, over time. Analysis involved identifying key storylines and themes and drew on conceptualizations of transition and continuity.Results: The participants' stories revolved around two themes: continuity within leisure over time and social engagement as a work in progress. The participants demonstrated differing patterns of achieving continuity within leisure and worked to maintain social engagement in the face of continually evolving social networks.Conclusions and significance: Findings enhance understandings of transition, continuity and the transactions between person and place that shape leisure and social engagement over time. Occupational therapists can consider community occupations from a transactional lens within services and policy to better support older women's participation and inclusion in neighbourhoods.