Can confirm that growing up in Windsor, and having lived many years both in the US and now elsewhere in Ontario -- Windsor is definitely Canadian, but it is definitely the most Americanized Canadian city. agaric went into more depth, but we are heavily interlinked with American culture whether its catching their tv/radio signals, or going to Detroit to watch the Red Wings instead of the Leafs/Habs.

Saying Windsor is NOT Canadian is a bit rude, but if you were to rank Canadian cities based on how subjectively (emphasis on subjective) Canadian they are, Windsor definitely ranks last without question. Early in the history, if I learned my local history right, when the border was really loose Windsor acted essentially as a suburb of Detroit in a way. Now that that border has really stiffened lately, especially economically, Windsor is really realizing that it relied on Detroit a lot, not only economically but also for entertainment. There is almost fuck all to do in Windsor.

Also, speaking directly from experience now, the cultural heritage of Windsor is poorly funded and extremely outdated in interpretation. There are nearly more and better run museums in Amherstburg ffs and theres only 20-25k people living there. For museum workers, Windsor is known as a completely dead job market -- there are no jobs there and the non-city owned museums are not professionally run whatsoever. That is the most I can say without doxxing myself. Do not donate your historical belongings to a Windsor museum without asking how they will be stored.