This paper has re-analysed and compared data between three studies conducted in the United Kingdom and in Sweden (the OPUS 'Older People's Use of Unfamiliar Space' study in the United Kingdom and the Swedish studies 'Let's Go for a Walk' and 'Walking in Old Age') to provide a comprehensive account of the issues facing older people in the outdoor environment. All three studies draw on the 'fit' between the person and their environment as a guiding conceptual base - capturing the dynamics of the relationship between older people's personal needs and their wider environmental context. This common conceptual base allowed us to test theory against practice, and to explore the utility of this concept across different geographical contexts. Participatory research was also applied, highlighting the importance of the voice of older people and involving older people in research. The studies also used a mixed-method approach involving both quantitative and qualitative methods. The paper highlights that although not generalisable, you can compare cross-locales and cross-nationally using different methodology; it investigates the challenges of cross-national comparative analysis and draws on findings from the three studies to illustrate the different challenges and solutions and finally looks at lessons that are transferable.