I am not a runner, but my wife is an ultra-marathoner. Her longest race is 100 miles (160 km). She advises running with a group, and also is an advocate of chi running (look it up on google). It is a low-impact way of running, which is designed to be more natural and causes fewer injuries. She recommends Gord's Running Store for shoes and gear. You should pick up a copy of the book Born to Run from the library - it is an entertaining book, and all of the ultra-runners that I know love it. I've even read it, and I can attest to the fact that it is a good read.
She is a member of the Calgary Road Runners. You might want to check them out as they organize group runs and training.
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