Vessi makes hiking shoes but specializes in waterproof everyday footwear rather than hiking gear, so their hiking options likely don't match dedicated outdoor brands.

It's been a while since I looked myself (not using the ones I bought all that often so they look almost new), but I don't recall coming across any Canadian ones unfortunately.

At first I thought, Arcteryx has been doing some hiking shoes/boots, but they haven't been Canadian owned for over 2 decades and I found them a bit too gimmicky personally.

As for what to look for, you need to realize what you find comfortable. For example I need arch support and wider toebox. You're gonna be wearing them for extended periods of time and you don't want blisters/discomfort.

I ended up trying a bunch in various shops and ordering a pair of Danners (not Canadian) online from a place where I could do free return, in case they didn't fit. It was the closest to my need, but I still had to get additional insoles for arch support.

Once you think you got it figured out, do yourself a favour and wear them at home for a few days, and see if anything is rubbing etc. "Breaking shoes in" is bollocks, mine were leather and didn't require any breaking in.

Hope that helps at least a little bit

Not Canadian, but Hanwag makes amazing boots in Germany.