A lot of places in Flanders were liberated by Canadian forces. I don't have a list, but as an example, on the Steen Castle exterior in Antwerp (not open to the public) there is lovely Thank-You plaque to the regiment that liberated the Port of Antwerp. Because I happened into a remote Deurne (neighborhood of Antwerp) bar on what turned out to be the early September anniversary, I had quite a personal encounter with locals who had just been to the cemetery to lay wreaths. And I mean to say that my money was no good at the bar that afternoon.
Bruges is definitely a beautiful place, but I don't think you will have up close and personal encounters with locals. Of course, that can happen anywhere. But if you can possibly work up the time and interest for a less prominent town (like Lier, Leuven, or Turnhout, none of which counts as "obscure", or Mechelen on Saturday market-day) you may possibly meet locals while walking around. For that matter, there is a Vrijdag [Friday] Market in Antwerp, but it's kind of Polish-trader commercial, to me.
The reason I mentioned Turnhout is that it corresponds (but is even better) to Rick's recommendation of Haarlem over Amsterdam. It's a prosperous local town (I mean, mainly postwar reinforced concrete ... .... ) with a magnificent Cathedral with superb woodwork inside, an Art Deco town hall that was actually open to the public last time I was there, an pretty Beguinage, including a formal museum, and with an old-folks center where you can buy coffee and cake, an obscure but famous Playing Card museum, and a respectable number of older buildings, including a castle now occupied by a financial services company. (One reason their tiny Beguinage has a nicer feel than the massive and famous one in Bruges is the degree of gentrification that has been necessary (?) in Bruges to preserve the place. The old-folks housing has less physical impact on the Beguinage.) I'm not at all saying you must go there, I'm just responding to your most recent post.
I absolutely adore the Beguinage in Leuven, but it's out of the way. This is kind of a University town, so the locals may be too young for you. But prices are lower as a result. The Beguinage in Mechelen is substantial, but suffers greatly from modernization, while maintaining most of the winding floor plan. It's more of a "ghost" of the Beguinage. But it's a lovely, quiet, un-crowded walk. There is a substantial Jewish history museum in Mechelen, but I've never found it open. There's also a museum that has a lot of the native-son painter Rik Wouters, who is little-known in the US, but is often called "the Matisse of Belgium." I love his work, but Matisse was much better! The little Mechelen Town-Museum has a huge collection of composite-event (and gruesome!) Lives of the Saints paintings, which are less common in US museums.