I really enjoy listening to Gordon Lightfoot's music, because he has some great hits like Early Morning Rain, Canadian Railway Trilogy, and so many more. I think he is a great folk singer/songwriter.
Another person would be Stan Rogers. I really enjoy his music like Make and Break Harbour, Barretts Privateers, and Northwest Passage. Unfortunately he passed away in 1983, but his music lives on.
And there are other singer/songwriters from Canada, like Gene MacLellan, Ian and Sylvia Tyson, Garnet Rogers, so many great singers.
Steven