Bill in Houston from Houston on 2/5/2021 12:47:06 PM:
The big thing will be to call ahead and make sure that the services you are counting on are available on the day you want them. Like, actually pick up the phone and call on the day before. Because if you roll into Mokane at dark-thirty expecting to get dinner at the bar and grill, and for some reason they are closed, then what?
That said, here's where to eat if you choose to have nice simple local food amongst the nice local folks.
Windsor - Wagon Wheel
Sedalia - Bothwell, I guess.
Pilot Grove - Deon's or Casey's (sorry, man, that's the best food nearby)
Boonville - Main Street Diner
New Franklin - no idea.
Rocheport - Merriwether's for breakfast
Jeff City - Central Dairy for ice cream
Mokane - Mokane Bar and Grill
Food is kind of a blur after that, except that Treloar Bar and Grill was great.
As far as history or sights, buy Dufur's trail guide and it will point out all those.