I’ve joined the Calgary Trail Runners a bunch of times and they are an awesome group. Lots of crazy people, lots of varied trails, and definitely hard core when it comes to trails. Kananaskis, Canmore, Banff trails mostly, but some trails in the city. They are all-weather folks who can’t get enough of the trails. Not all the trails are really hard or long, but you can’t see the city or highway from most of them.
Check ’em out.