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Travel from St Louis to Nashville or Memphis or Louisville - When?

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That is a huge hole in the SC network. Here's hoping Tesla plugs (pun intended) sooner rather than later. This is holding me back from buying a Tesla as we travel to southern Maryland via 64 to visit my SIL/Daughter and new grand daughter every other month.

So for now we own a Gen I Volt as our DD (over 93% all electric) and a 2016 Equinox for our long distance vehicle (we travel with our dog) and a MS could replace BOTH vehicles if I could make that drive w/o jumping through hoops and in the winter.
 
Yes, there are lots of hole in the Supercharging Network.
And TM is working on some of them (see the Arkansas Supercharger Desert).

From my point of view, you can absolutely get from St. Louis//Belleville, IL to Maryland right NOW using your MS.

Use US70 across IL, IN, OH, WV, corner of PA and then head south thru VA to MD.
More than one way to skin a route using an S85 or a S90.
Slightly not the most direct route, but still very viable, almost any time of year.
Just take it easy in the Smoky Mountains.

I did a similar trip last September heading West thru Baltimore to KC and Topeka.
And it will give you to stop and visit Shanksville Flight 93 Memorial, Air Force Museum in Dayton (and they have free charging there too!), maybe Fallingwater @ Bear Run in PA.
Maybe stop and take in a museum or site in DC.

Flying may be faster, but you can't connect with lots of areas and sites from 30K feet.
 
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Mt. Vernon, IL is screaming for a Supercharger. It's at the intersection of I-64 and I-57. It's a little far from Louisville (182 miles), but it would fill a huge void between Louisville and STL. There's really not a good place to put a charger along that route (Evansville is the only other sizable city, but it sits pretty far off of I-64). My sister lives north of STL, and if want to visit her, I would have to go Louisville-Indy-Champaign-Springfield-Quincy, IL. It's a far more direct route to go Louisville-Mt Vernon-STL-Quincy.