This morning I went down a bit of a rabbit hole browsing municipal flags of Ontario on the Flags of the World site. Here's some interesting or notable ones I've found so far.
Toronto - Toronto certainly has the nicest flag I've looked at today with the distinctive white stripe representing city hall and the maple leaf gives it a nice touch. The flags aren't necessarily all downhill from here but there are clearly different levels of quality.
Also shout out to Cabbagetown on that page with it's flag being a literal cabbage. No deep symbolism here.
Muskoka District - Runner up for my favourite flag. It's simple and distinctive with some pleasant colours. The blue representing the abundant lakes and green for the wilderness.
Guelph - Nice design. Feels old world European. Also the horse looks a little high to me so it's a good representation for the University of Guelph. Also take note of the old flag on the bottom which is a good example of the bottom of the barrel in flag design.
Gravenhurst, Tillsonberg, Oxford County, and Oakville - These guys all went the corporate logo route. It's interesting how there's a very distinct feeling for me between a flag and it's symbolism and commercial branding. I think it's mostly the inclusion of text on the flag.
Midland - This one is pretty out there with it's gold cross with pine trees on the ends and ships wheels and cog wheels included. I kinda like it.
Windsor - I'm just surprised it isn't a pizza flag because if you run into someone from Windsor apparently the only good thing about the place is it's pizza.
Hamilton - Funny I should like this one. It's got a good design with some nice symbolism. Maybe it's the yellow? Or maybe it's just because it's Hamilton. Also the old flag despite being crap has some nice elements to it. I kind of wish they'd incorporated the line representing the escarpment in the new one.
Petrolia and Palmerston - Not great designs but note the areas history. Petrolia was the site of North Americas first commercial oil well. They've got a nice museum that's worth visiting if you're out that way. Palmerston was once an important rail junction for that area of the province.
Kapuskasing - Poor Kapuskasing. Stuck with MSPaint and Windows 98.
Anyway I'm hoping some of you can share some interesting local gems that I wouldn't otherwise be aware of.