Michael,
During various periods of the 18th and 19th Centuries, NYC and Montreal were "rivals" as export centers to Europe.
It was most "telling" during the hey day of the fur trade. Montreal had better connections to the continental interior (i.e. source of supply) whereas NYC had a year-round port (as you know, Montreal becomes ice-bound in Winter). That meant that the longer distances from the interior to NYC were less of a competitive disadvantage than they might have otherwise been. [If you look at the New York State emblem - it includes a beaver - and not because they are "cute").
I always enjoy visits to Montreal because it is m/l the same "vintage" as NYC and so has the many-layers of history that one doesn't find in say Chicago or Toronto.
Although, to be honest, one has to go to Quebec City, or down to Mexico City to find really old "Euro roots" (with the latter even going back to pre-Columbian times!).
Thanks for the fur trade detail, I always think of fur trading as the only thing that ever happened in Canada, and nowhere else either.
I agree with the Euro beat of Québec and Mexico City, having visited both. The Zocalo cathedral always awed me for having been started in the 16th century (but the Aztec constructions take the biscuit for awe-inspiration, nonetheless).
Montreal's "euro vibe" is more the result of the last 20 years of sucking to the French to be their friends than of the last two hundred years. Montréal is for me a North American city first in its history, and I find the similarity with New York flattering for both towns.