Hi, Matthew! This is not really on topic, since you're asking about bar gigs, but may be another idea-
    With my balladeer group in rural NY, USA, I just went ahead and started contacting non-profits (not just concert halls, but also libraries, assisted livings &c), scheduling full-length free or pay-what-you will concerts. I handle all the promotion, and can usually turn out 40-60 people in our small towns (our village's population is about 1800). It's gotten our name out a lot better than doing open mics.
    This year, we're mostly doing suggested donations, splitting 50/50 with the venues, and selling our CDs.
    Church fundraisers are also a good connection- we were paid for doing the first half of a Veterans/Remembrance Day concert, followed by a large Barbershop chorus. This had the advantage of us hooking in with an existing group's following, and we got a lot of requests to return.*
    Again, not being familiar with Ontario I don't know what the situation is there.
    Best,
Kristoffer
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    * At the Veterans Day event, We did a rather reflective, serious set, ending with Flanders Fields and The Band Played Waltzing Matilda, while the Barbershops did a sort of "the USA is the greatest country in the world, so God Bless it!" patriotic selection. A number of people mentioned that they appreciated the former view better...