This study used a phenomenological approach to explore the relationship between habitual occupations and environmental features that can support aging-in-place with 10 community-dwelling older adults. In their respective interviews, participants were asked to consider community supports and other adaptations they used to maintain participation in response to changes as they grew older or encountered health difficulties. From the transcribed data, themes were identified using an open coding process and verified by an external peer auditor. Results underscore the inextricable link between older individuals, their environment, and maintaining participation in habits of meaning. Findings are discussed using a transactional model of occupation, namely dynamical systems theory. By using habits as the central focus, this study provides a unique opportunity to examine how key supports at a community level, including design of the physical environment and other policies, can promote continued participation in older adulthood.