From Google Maps, distance approximate:
Whitewood to Regina - 170km
Whitewood to Moose Jaw - 240km
So it would be nice to have some charging option in Regina for the winters.
But then, Moose Jaw to Maple Creek - 310km, while Moose Jaw to Swift Current 170km
I assume Swift Current is still a necessary stop and a supercharger is planned for there, as well as Medicine Hat.
The other direction - much easier to traverse in any weather...
Whitewood to Brandon - 180km
(I though Musk's mother was from Moose Jaw).