In spite of the large-scale growth of walking sport (WS) programmes globally, limited research has explored the experiences of the key stakeholders involved in such programmes (i.e. decision-makers, facilitators, and players). We aimed to explore stakeholder experiences of community-based WS programmes to better understand the appeal of such sport options for middle-aged and older adults, and propose tentative recommendations for the feasibility and sustainability of these types of programmes. We conducted semi-structured interviews with 21 stakeholders who were involved with WS programmes in Australia as decision-makers, facilitators, and/or players. Data were analysed with reflexive thematic analysis. Four key themes pertaining to the WS experience were identified–‘a renewed lease of life’, ‘navigating ageing stereotypes’, ‘tension between organisational demands and players’ needs’, and ‘WS facilitators as catalysts of success’. Specifically, we found that WS participation enabled a positive ageing discourse for middle-aged and older adults. WS players had to negotiate stereotypes that, at times, were perceived as participation barriers. We also noted some tensions between the demands of sport organisations and the needs of middle-aged and older adults regarding sport participation. Finally, we also noted the importance of the facilitators’ role in increasing accessibility of, and long-term participation in, such programmes. We suggest that to offer feasible and sustainable community-based WS programmes across Australia, incompatibilities across various stakeholders’ perspectives need to be addressed. © 2023 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.