Because the car battery cools down in cold, it cannot output as much power as it could in the summer, therefore the range drops (people report as much as 40-50% in extreme cold). But if you drive a long distance non-stop, e.g. to Winnipeg, then the battery should warm up and increase the range. Pre-heating the car helps a lot too.
There is a video blogger on YouTube, Tesla Bjorn from Norway. He owns a Tesla, but he's also testing different electric cars. He has many videos about winter driving, e.g.
You could also find lots of forum discussion by electric car owners (mostly about Tesla cars, because they have the longest range among electric vehicles and a really good thermal battery management).
E.g.:
https://teslamotorsclub.com/tmc/threads/no-garage-for-my-tesla-in-canadian-winter.86920/
https://www.reddit.com/r/teslamotors/comments/7ngdxr/tesla_in_the_canadian_cold/
There are some great youtube videos as well. Such as by a family from Alberta:
As far as I know, there is a network of fast chargers for Tesla cars, called superchargers, and you could find a map of them for USA and Canada
https://www.tesla.com/en_CA/supercharger .
Seems they plan to build superchargers along the Trans-Canada, inducing Brandon, Portage la Prairie and Winnipeg.
There was a plan to build a number of fast chargers (non-Tesla) to connect Winnipeg and Toronto.
https://www.plugshare.com/
is a great website to check charging stations in your area or on your route.
I think that owning an electric vehicle, especially in cold regions like Manitoba, requires planning and understanding of the limitations. It's not yet for everyone. I'd love to own one, though.