Southwestern Ontario is in a weird spot because of being smack-dab in the middle of three Great Lakes. So while places like Boston and Buffalo and Cleveland get the ridiculous snow and wind from lake effect we seem to be in a sort of negative area. Not to say we don't get the odd 5-feet-dumped-on-us-snowmageddon now and then, but the last few years have been super, super mild.
tl;dr winters aren't all that bad in several key areas of Canada. But obviously we still get some snow and cold here and there.