Too bad yyc isn't with us anymore. Then again, he might just show you the bovine attractions.
Assuming you're driving from Toronto, it'll probably take you 3 days to get to Calgary. Day 1 you should make it to the north end of Lake Superior - perhaps around Thunder Bay. From here you have a choice of a northern route or a southern one. Both routes will eventually take you through Winnipeg but the southern one goes through Michigan. This may or may not be a problem driving through the US depending on how anal they're being about terrorism at that time. Personally I've always done the northern route.
Day 2 you should make it to Saskatchewan - Swift Current or Moose Jaw. From there it's an easy drive to Calgary.
In Calgary a bar that has drop dead gorgeous ladies is Cowboys. It's neat because the ladies are all good looking and they don't have attitude.
Personally I only go to Calgary for business. For fun I usually head up to Banff (2h drive). Once there I just hang out enjoying the scenery or do some of the easier trails.