If you want to test your metal, literally, every other year one of the Rocky Mountain Land Cruiser club guys organizes a winter northern run from Calgary north though Yellowknife and beyond - gotta be able to start at minus 30 or so (and it doesn't matter if you read Celsius or Fahrenheit).
For a warmer summer run, with Calgary as a start, it's two long days to Whitehorse (21-23hrs), but you feel like you hit a different part of the world once you get to Muncho Lake, from there, you are in the mountains, driving past long (cold) lakes, wildlife abounds, including a herd of bison that hang out around the highway near the Yukon BC border. Once in Whitehorse, you have options to head south to Skagway at the top of the Lynn Canal fjord (about 2 hours away), Kluane National park, 3 hours west and on the way to Haines AK (5 hours), Valdez, Anchorage, Kenai peninsula, Denali Mountain (Anchorage is 11-13 hours) or Dawson City Yukon, about 6.5 hours - or even Tuktoyaktuk up the Dempster Highway (20 hrs from WH). Best time of year is June/July, long days, warmer, pre-blackfly season.
This is 10 min behind my house: