Community participation during the cold winter months is difficult for wheeled mobility device (WMD) users. However, limited attention has been given to understanding this problem, and collaboratively identifying solutions with stakeholders. This qualitative study explored the issues faced by key stakeholders (WMD users and Public Works Department employees) regarding use and provision of accessible sidewalks in winter and identified solutions. Eleven participants informed the study through a combination of go-along interviews, key informant interviews, photographs, and meteorological data. Four themes were identified: the context of winter season, winter and wheels interact, winter versus the city, and a framework for winter access and success. Solutions included creating awareness, taking action, and assuming accountability through collaborative efforts and increased information sharing. Based on the perspectives of informed stakeholders this study contributes to the development of focused interventions for overcoming winter sidewalk barriers and thus, enabling winter community participation of WMD users.