It didn't need a fancy name at all. I suspect Winterlicious was the brainchild of some marketeer. It's typical failed marketing, in that the name doesn't tell you what you're promoting. Is it a winter festival, is it outside food vendors, if it's inside where the winter connection, is Sid Vicious (sp?) involved somehow?
Do you remember those Taco Bell commercials with the Chihaua dog. That ad campaign tripled sales of, you guessed it, Chihaua. Taco Bell did not benefit as nicely. That's the power of marketeers let loose without supervision.
Simply calling it Dine Out TO or something along those lines would have sufficiently communicated that it was about Toronto, it was about Food and it was about going out to get it.