Practical
Wind, French across the river, and YWG
Cold-weather clothing is not optional from late autumn through early spring. A downtown coat that works in Toronto can be inadequate on a Winnipeg river path in January. Cover your face for the wind, and plan indoor segments. Hotel desks are used to the climate. They are not a substitute for boots. If you are travelling with someone who cannot walk far in that cold, choose the shortest exposed distance and say so when you book elsewhere.
Saint Boniface is French in a way the rest of the city is not. You can spend a morning there, see the cathedral quarter, and come back across the river. Festival du Voyageur, in winter, belongs to that side of the city as a seasonal event. This guide does not sell admission. YWG is northwest. Give the airport transfer extra minutes in a blizzard, and do not treat a clear-day estimate as a promise.