Oshawa here too for “never heard of”. Unfortunately, I have never visited Toronto or Montreal. (Well, arguably not “unfortunately” :), but you get the idea)
Largest one I have been to is Halifax. I don’t travel much.
First one I didn’t recognise was Barrie.
I’ve never been to Calgary (#5), and I’ve never heard of Barrie (#21).
I went through Calgary on the way to Banff.
Outside of that, I spent a few nights in Nelson, BC once on spring break.
Largest one I haven’t been to: Vancouver #3 (but hopefully that will change soon)
Heard of: #51 Granby
Pygmy Rugger its:
Gretzky
Dumb fact: Kitchener, ON used to be called “Berlin, ON” but was changed during WW1. (Cite.)
Never been to: Montreal (2) (Which is sad because I live in #9.)
Never heard of: Saint-Hyacinthe (57)
Never been to, oddly enough, Quebec city (7). Never heard of Kelowna (22).
Never set foot on Canadian soil. Oshawa was the first one that stumped me. Below that, I knew exactly a dozen of them.*
"To be fair, “know” means “heard of”, not “able to pinpoint with accuracy on a map.”
largest I haven’t been too is Saskatoon, which will be remedied in a couple months.
I have heard of pretty much all of the cities except for a handful of ones in Quebec starting with Saint-Jean-sur-Richelieu.
The largest Canadian city I have never been to is Ottawa, and I’d really like to see it. The largest city that I had never heard of was Wood Buffalo Alberta.
Haven’t been to #1, Toronto, and haven’t heard of #14, Oshawa.
Wood Buffalo is another one of those bogus agglomerations. It’s more properly known as Fort McMurray.
I haven’t been to #3 (Vancouver). The highest I’ve never heard of is #18 (Sherbrooke).
I’ve never been to any other province than Ontario and Quebec. I"ve been to probably 80% or so of the Ontario locations and half the Quebec ones and there’s only a few for each of those provinces I haven’t heard of. There were a lot more near the bottom of the list for the other provinces. The first one I hadn’t heard of was Vernon, BC (#58).
That’s my hometown, didn’t know it would be #11 on the list though.
Huh. Well, that saved me some typing.
Ditto.
Other than to turn around at the border with Idaho, I’ve never really been to Canada.
Looking at the list, the first one that I did not recognize was Kitchener (Cambridge, Waterloo), #11.
Biggest that I haven’t been to is Vancouver. Biggest I haven’t heard of is #24, Kelowna, BC. In my defense, Kelowna is a town of 150,000 on the other end of the continent. And what’s striking, when you compare this list with the American one, is how fast the drop-off occurs, from big to not-so-big. Number 100 on the list has a little over 20,000 people, which in American terms, is basically a village. I’ve been to Saint-Jean-sur-Richelieu (#43) and Granby, QC (#49), and it’s really hard for me to read those as top-100 towns.
The biggest I have never been to is Montreal (#2), and that I hadn’t heard of is Salaberry-de-Valleyfield (#74). Actually, that’s the ONLY place on that list I had not heard of before today.
You’re not a broken man on a Halifax pier, are you? Either way, damn them all! It’s gonna be stuck in my head ALL DAY.
My hometown (Calgary), and my adopted hometown (Banff) from someone whose hometown (Baltimore) is where I now reside. Nelson, BC is probably known best as a movie location because of its quaint charm. It was the town in “Roxanne”, with Steve Martin.
You and I both know - being Albertans - that Raygun99 is right. The city is McMurray and the buffalo are buffalo. What a load of hooey.
Biggest never-been-to: Calgary
Biggest never-heard-of: Brantford, Ontario
I’ve lived in the top three Quebec areas (Montreal, Sherbrooke, and Québec) (not counting Gatineau, because that might as well be Ontario 
) and visited many others.
I’m with Sal, there’s an awfully big drop-off somewhere around this list’s late teens-early twenties. I suppose some of that’s because this list’s definition of metropolitan area is a little shaky. I mean, Laval is lumped in with Montreal, though you’d have to search a long time for a Montrealer or Lavallois who’d count these two cities as a unit. (I suppose a cartographer could call them the Greater Montreal Region, but no one who lives here does.) If Montreal and Toronto were divested of the cities cleaved to them, and those cities were considered separately, I suspect some of the smaller areas would be bumped off the list.
Another surprise for me was seeing mining towns like Val d’Or (#82) and Thetford Mines (#92) on this list too. <Tongue-in-cheek trucker hat on> You may be a redneck country when you’ve got towns on your top 100 list that are threatened with closing every couple of years. <Tongue-in-cheek trucker hat off>
I’ve been in Canada once (Toronto).
I had never heard of Sherbrooke before, but I’m familiar with many of the lower ones on the list. Some places like Yellowknife are not even in the top 100.
I see Sherbrooke is about the same size as Panama City, FL. I’m not sure if that means I should have heard of it or not.