Interesting question to consider, and I’ve done a lot of it since reading Colin Woodward’s American Nations. Woodward’s main argument is that North America is divided into a dozen or so distinct nations, founded by different groups of European settlers who established foundational institutions and the dominant political attitudes. These founding people, even as they've become tiny minorities over time, still set the tone in these nations today. The book focuses on the U.S., but the map shows Winnipeg located within the Midlands nation, which originated in and around Philadelphia in the late 17th century. Founded mostly by Quakers. The Midlands, as well as Yankeedom (eg, New England) spread westward in the 18th and 19th century.
Within these nations is a whole strata of class distinctions, rural-urban divides, and a broad diversity of ethnicities. But dominant cultural patterns remain in place. (For example, New York City hasn’t been controlled by the Dutch for 350 years, but the city still follows in the same pattern of being business-minded and socially progressive/permissive its Dutch founders.) Everyone who arrives later from elsewhere basically ‘signs up’ for being part of this nation.
Somewhere not far to the west of Winnipeg and the Red River to the south of it, according to Woodward, the Midlands nation ends, and the Far West begins.
Up close, of course, Winnipeg is a little more complicated. Today’s Winnipeg is made up of at least two nations: English Canada of Ontario (which is also located in Woodward’s Midlands), and the Metis/French nation east of the Red River. Maybe there’s also a founding Orkney Scots and English-speaking Metis nation of the Selkirk Settlement, distinct from the Protestant British and Ontarians who began to 1860s and would spend the next 75 years building and ruling Winnipeg. I really don’t know how different and unrelated these two groups (Selkirk Settlers and English-speaking Metis, or the Ontario latecomers).
Historically, politically, and culturally, I see Winnipeg more as a remote outpost of Ontario and the American Upper Midwest than I do as the eastern edge of the Canadian West (Western MB, SK, AB). Similar to how St. Louis or Chicago were considered gateways to the American West, but are themselves Midwestern cities.
There is no Canadian Midwest – politically, there’s the three Prairie Provinces; geographically, there’s just one big triangle of inhabitable prairie and parkland surrounded by uninhabitable rocks – but I certainly think of Winnipeg (and the rest of yesterday's Red River Settlement, and today's Capital Region) as its own distinct animal within Western Canada and the Canadian Prairies. This is probably as distinct of a difference as there is between Winnipeg’s street system and that of almost every town and city to the west of it. Our city is built on a 200 year-old river lot system and far older trails used by Indigenous people and fur traders. Western cities were almost all built around the Dominion Land Survey system and rail lines of the late 1800s.
Architecturally, and the way many older parts of Winnipeg feel, I think is more akin to Indianapolis, Milwaukee, or St. Paul. I imagine it’s the same with regards to attitudes and manners.