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If you're looking for public transit, avoid Calgary. Yes, the C-Train is handy, and the buses do run to schedule; but bus routes could be much better planned. Unlike Toronto, where buses follow main roads (e.g. the Sheppard East, the Lawrence West, and so on); Calgary buses meander through neighbourhoods. This is great if you don't want a long walk to the bus stop, but lousy for getting to your destination in a reasonable amount of time. Of the two cities, I'd suggest that Montreal has better public transit.
That being said, there is something about Calgary that would make me recommend it to somebody who likes to ride their motorcycle. Banff and the mountains are just over an hour west, but there are plenty of interesting places to explore east of there (the Kananaskis and Canmore). Or, head down Highway 2 to Waterton Lakes National Park--another mountain park, and one that is rarely crowded in summers, unlike Banff.
Summers in southern Alberta aren't bad. Hot and dry, though June does tend to be rainy. You can garden, and I've raised some fine tomatoes in my back yard. Winters can be fierce though; and unlike Toronto and Montreal, Calgary does not plow all streets. Major ones, yes, but expect residential streets to be snow-covered for months. Chinook winds provide some respite during the winter.
There is some charm to Calgary, but you have to look for it. The downtown does have some interesting old buildings and architecture; but sadly, there are many more faceless modern structures. Still, it's fun to explore the downtown, and discover Calgary's history.
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