Rural communities are ageing more rapidly than urban centres due to changing demographics and preference for ageing in familiar communities. Concurrently, ageing in place policies have progressively reinforced community living as the best option for most people. For ageing in place to be successful, understanding the relationship between the community environment and the functional ability of older adults is crucial. Yet, little is known about the relationship between older adults and their environment during their everyday experiences in diverse rural communities. This article reports on the findings from walking interviews with 15 older adults as they negotiated their physical environment in a rural community in New Zealand. Dewey's transactional perspective and theory of inquiry were utilised to view the everyday transactions these older adults were undertaking while being out and about doing what they value. A Deweyan perspective enabled a deep understanding of how participants negotiated and renegotiated their environment as they encountered indeterminate situations. The three main categories identified from the data: negotiating changing capabilities in a changing environment; negotiating the environment safely; and negotiating access within the environment, captured the holistic nature of the participants' everyday transactions and their continually changing relationship with their environment. The observations and discussions during the walks uncovered problem-solving and active citizenship as these older adults undertook their own ‘commonsense’ investigations of their environment. The findings highlight the valuable contribution rurally living older adults are making as active citizens during their everyday transactions. Understanding the resourcefulness these experienced older stakeholders bring to their rural communities is the first step in active collaboration at the local level. Mobile research methods are a useful means of capturing real-time experiential data in an inclusive and creative way.