In many places thought to be leading the movement towards climate-resilient cities, the importance of encouraging multi-modal transportation options is critical in not only reducing emissions and positively affecting public health, but also allowing for design opportunities. When the car-centric model is challenged, opportunities arise to implement designs that have both environmental and social impacts on the city. However, in cities where the cold temperatures grant the designation of a ‘Winter City,’ there is little to no research done on how to adapt these multi-modal models. In this practicum, the relevant themes of a bike-friendly city will be adapted to the context of a Canadian winter city, such as Winnipeg. These themes will be explored as possible catalysts in changing mentalities surrounding winter cities.