Plausibility Check- Major City on the Mississippi

I've had an idea for a tl following the development of a hypothetical city on the Mississippi called Rome. It would be on the Kentucky shoreline. However, I need to know whether it would be plausible for a city could have been formed by the Order of Cincinnatus in this area. I also need to know whether this city could have evolved into a whiskey trade based city, and how large a combined machine tools, whiskey and steel based city could grow too. How about if they added automobiles and agriculture to the mix.
 
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Around OTL Paducah would be your best bet in Kentucky, even if its only near by the Mississippi. Especially if its the states doing the settling.
 
Cairo was a major river port until the coming of the railroads. Not faniliar with the topography but could Cairo be more susceptable to flooding than say StLouis
 
well both places have dikes today. I think that St Louis in otl had the advantage of an earlier start and better access to the Missouri river fur trade. And Cairo is right at a confluence of rivers while St louis is a few miles away from one.
 
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The 2011 flood
Cairo-IL-4.30.11-Cor.3.jpg

The Mississppi is the river on the top, both flow from right to left in the pic.
 
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Tennessee is prime cotton country, I'm more interested in corn country up north. I was thinking Kentucky because of the bourbon producing regions already around there, the coal nearby as well.
 
What about Kaskaskia, Illinois? It's near enough to the lead mines in Missouri that it could thrive in the 19th century. There would need to be some extensive flood management though, since the Mississippi is wider and shallower in that area.
 
St Louis is also near the Illinois River confluence, which is as good as any route to the Great Lakes basin. The Ohio, connecting to the Tennessee River, Wabash River, and nearly to the eastern Piedmont is not close but not too far away. In terms of water transport St Louis is close to the hub.
 
To those wondering why Cairo, Illinois never developed - a combination of horrific racial strife and being devastated regularly by floods and tornadoes of a biblical scale.
 
I've had an idea for a tl following the development of a hypothetical city on the Mississippi called Rome. It would be on the Kentucky shoreline. However, I need to know whether it would be plausible for a city could have been formed by the Order of Cincinnatus in this area. I also need to know whether this city could have evolved into a whiskey trade based city, and how large a combined machine tools, whiskey and steel based city could grow too. How about if they added automobiles and agriculture to the mix.

I'm afraid a major city in the Jackson Purchase area wouldn't be terribly likely, TBH: not a lot of good land there.

If you wanted to try it, St. Genevieve, Mo., had some promise; maybe not as a rival to STL but it could've still been something-same could be true for Kaskaskia, Ill., too, as other have mentioned.

There's also the Quad Cities-Rock Island and Moline, Ill., were especially good places for a city, but Davenport and Bettendorf in Iowa, as well.

You could even try for Baton Rouge in Louisiana, though it might have to involve a major disaster in New Orleans(Katrina 200 years early?).

To those wondering why Cairo, Illinois never developed - a combination of horrific racial strife and being devastated regularly by floods and tornadoes of a biblical scale.

Not to mention the geography-the city is actually rather narrow, on a peninsula only around 10 sq. mi., last I checked.
 
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