Don’t know which way you are going but you can do a tour of Churchill Downs in Louisville or the Kentucky Horse Park is nice in Louisville. There’s also a restaurant Claudia Sanders, related to Colonel Sanders of KFC but not fast food, in between the two cities that’s interesting to stop at. |
Near St Louis - Cahokia Mounds State Historic Site
Consider a detour on your way there or back to Springfield IL for the Lincoln sites. The tomb, library, home, and nearby New Salem where Lincoln lived as a young man are all interesting. |
I love Louisville but we find the northern route (Through Columbus) much easier driving. I have gotten caught in the mountains in WVA where it suddenly got dark and very misty/drizzly with super bad visibility one too many times.
Some nice things to do around/in Columbus. We usually stop there overnight, but that's b/c we have friends there. I think there is some sort of big train museum near columbus. |
Falling Water on the way
And another vote for the city museum. |
Indianapolis has a decent kid's museum, if you want to get them out of the car for a bit. |
If you are in St. Louis and want to see the prettiest part of the Mississippi River, the drive to Pere Marquette State Park on the Illinois side is gorgeous. There's a small waterpark in Grafton called Raging Rivers that is fun. The kids can play and you can have a beer and watch the river go by. |
Stop in Louisville KY or somewhere in WV, depending on how far you want to get on day one.
You MUST go to city museum in St Louis if it’s open. I don’t want to water down my city museum suggestion with others but there’s also forest park, the arch, delmar loop. If you like blues or bbq check those out. Be aware that the city itself is not in great shape (white flight and lack of funding). That said it’s perfectly safe to do any tourist things. I would probably not choose to stay in the city at night. Downtown Clayton or UCity are safer and more alive at night. |
St Louis restaurants/restauranteurs to check out:
Any Kevin Nashan, Ben Poremba, Gerard Craft place (Sydney Street Cafe, Peacemaker, Olio, Nixta, Pastaria,etc) Central West End (by WashU med) is the best city type experience available. Lafayette square has charming Victorian houses. Soul are is supposed to be funky/cool. Cherokee Street is hipster. |
^ that should say Soulard |
Pere Marquette is great! Lots of eagles in the winter. But beware OP that the Mississippi just isn’t that pretty...big muddy is about right. |