InternetDude, care to share some details as to your chosen route and where you charged?
Best chargers YQR --> YEG route is Vermillion 80A & North Battleford 80A, both are at malls. Also worth mentioning is Langham charger, it's 70A but 240V (single phase). I left notes in both the Sun Country Highway app and PlugShare so check them out for specific comments/reviews and other people's comments also. I will more than likely be doing the trip to Calgary in 2016 so I will try out the chargers on that route.
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Calgary (Airdrie actually) to Winnipeg...
Airdrie to Brooks - 208km's
I plan to use the Ramada Charger and top up the charge, its supposedly a 70 amp charger so i'll be there fore just under 3 hr
Has anyone charged here? i/e will the let non patrons use the charger?
Brooks to Medicine Hat - 107kms
Med Hat only has a 25 amp charger which i will be passing on, but can have as a backup
Medicine Hat to Swift Current - 225 kms
Leg traveled since last charge 332 km's
The Kal Tire in Swift has a 90 amp charger and i hope to use it over night if possible, there are store hours listed and i am not sure if that causes a hindrance. from what i read its behind a gate?
I am worried about this distance since i am unsure on the impact of inclement weather on the charge/range, thoughts?
Swift Current to Moose Jaw - 175km's
Moose Jaw has a 70 amp charger which i will be passing on, but can have as a backup
Moose Jaw to Regina - 72km's
Leg traveled since last charge 247km's
Regina has 70 Amp at the best western which i plan to charge at for 3.5hrs to get me enough juice to get to Brandon.
Regina to Whitewood - 175km's
Whitewood library has a 70Amp plug supposedly, will not be using it. backup however if the weather is causing significant range reduction...
I know you're flying now but I wanted to point out a few things. I did not want to say whether you could make the trip given your schedule, weather, etc as I have not done any real winter road trips yet.
Brooks Ramada - the comments seem to say that only paying customers can charge there. If I was in a pinch, I'd just charge anyway just long enough to move on to M.H. and deal with the consequences by management, especially in winter. My $.02. Fortunately Strathmore has a charger now thanks to gpetti so you could charge there instead and not stop in Brooks I would say.
Medicine Hat Peavey Mart has a 70A charger, not sure why you think there is only one 25A charger in the city.
Swift Current is a 70A charger, not 90. Read all the comments for all charging locations carefully. I personally phoned Kal Tire and questioned them about the charger. It is not behind a gate and is available 24/7. I put that in a comment in PlugShare for that location. It's in a fairly industrial area though so there's not a lot to do there while charging from what I can tell (I haven't charged there but I even used Google Street View to figure out what's nearby).
Moose Jaw charger is 70A and within walking distance to Boston Pizza and a few other restaurants, not a bad location.
Regina Best Western - not allowed to charge there unless you've paid for a room (even though they have a 80A Tesla HPWC AND 2 70A units!!). The Peavey Mart charger is 70A but there really aren't any close restaurants. It's on the edge of the city right on the highway so easy access though.
I can't comment east of YQR as I haven't done any real planning in that direction. As I said I've gone north/west to Edmonton and know I will go to Calgary so I've spent time figuring those routes.
As I said before and I think you should heed the advice is to stop at every city and charge on the way there (for even 20-30 mins per city) to confirm which ones work, which ones are fastest, what amenities are nearby, etc. (take notes). Then when you come back you can pick and choose which chargers you want to stop at. Oh, and tell Tesla why you are taking a flight instead of your wonderful car. They don't seem interested in Supercharging Calgary to Winnipeg, you're supposed to go through the US.