As connections are drawn between physical activity and the built environment, various elements have emerged as key contributors to the viability of walking as a form of transportation, including land-use patterns, architecture and landscape, and the transportation system. The resulting concept of walkability is strongly correlated with transportation physical activity. Developing efficient measures of the built environment is essential to the advancement of further research in this area. This project envisions enhancing walkability as an urban intervention to support community health. The research assesses qualities of the urban street environment that may improve the walkability of Winnipeg, identifying climatic gaps that exist in current walkability auditing tools. This research is based on literature review of the health benefits surrounding walkability, unobtrusive observation of three neighbourhoods, and a systematic review of seven walkability audits. The result is a set of research, planning and design recommendations for how to better design audits to reflect the reality of winter, in order to more fittingly assess and improve upon the walkability needs of winter cities in Canada.