The first step would be to get over to the river. But we'd happen to trip over Duluth on the way there from where we live, and Duluth has something I've always wanted to see: Aerostich! The moto-gear company has been in Duluth since the early 80s and makes bullet proof riding suits, including one piece coverall type suits that long distance riders swear by. They are weather proof, tough, protective and built to size, which is good when you have a weirdly long body on relatively short legs. I'd kick off our ride down the Mississippi by dressing like matching Ghostbusters!
Map 1: Home to the head of the Mississippi is about 1850kms. I've been that way before and have always wanted to show my wife the strange world of the Michigan Peninsula. Our first day would only be about 420kms over the border to the Bay Valley Resort then a bizarre evening in fading 1970's decadence. Day 2 would be 540kms along the tunnel of trees and over the incredible Mackinac Bridge and into Northern Michigan. Day 3 would be 470kms over to Duluth along the south shore of Lake Superior. Day 4 would be a loop from Duluth to Palisade where we'd finally pick up the Mississippi and follow it down to Minneapolis.
From here on south we'd be sticking to the Great River Road as much as possible. The site suggests 4-10 days to make that ride, so I'd aim for 10, or more.This is the kind of trip you could rush through if you were young and impatient, but I'm neither thing these days. In a post-retirement world this would be a good thing to kick off in the fall (October) and take extended breaks on the trip, getting into New Orleans just before Christmas and then staying around there until Mardi Gras in February. Doing it that way could allow for a winter in the south before working our way back up the Appalachians in the spring and home again.
The whole route is about six and half thousand kilometres. A three hundred kilometre a day average (some days off, other days over) means a 22 day trip. Cut that to a 200km/day average with more days off factored in and it's a 33 day trip, which isn't too heavy.The Great River Road: https://experiencemississippiriver.com/
Ground Zero Blues Club: https://www.groundzerobluesclub.com/
The route from Easy Rider: https://www.mrzip66.com/2009/04/route-from-the-movie-easy-rider-map/
Louisiana motorcycle routes: https://www.motorcycleroads.com/motorcycle-rides-in/louisiana
Mardi Gras: https://www.mardigrasneworleans.com/when-is-mardi-gras/
GRR G-Map: https://www.google.com/maps/d/viewer?mid=1E55lpa0LR6ElEsvujeCHdx2ucj0&usp=sharing
APPALACHIANS NORTH:
Appalachian Scenic Byway: https://www.alabamabyways.com/2013/01/01/the-appalachian-highlands-scenic-byway/
Tail of the Dragon: https://tailofthedragon.com/
Blue Ridge Parkway: https://www.blueridgeparkway.org/