Climate change is forcing northern cities to reconsider how people move about in a manner that is safe, reliable, resilient, inclusive, and low-carbon. Despite the growing knowledge of cycle planning and infrastructure for winter cities around the world, there is little cycling studies for small rural winter cycling cities. How have cyclists experienced northern cycling initiatives addressed to increase active travel in their home communities? The literature available currently on both small and large cycling cities studies overlooks the aspect of cyclist trip satisfaction and motivations for cycling. This study aims to (1) determine the winter cycling policies for small rural northern cycling communities in Canada, (2) determine the trip satisfaction and motivation of cyclists in 3 case study communities in both summer and winter months, and (3) better understand the cultural nuances and geographical characteristics of theses communities that foster a positive cycling environment.