I will probably have an occupied passenger seat or I would suggest a ride share. But that is only probable. Will know more as the time approaches.
As for stops and things to visit along the way, a few leap to mind right off the bat. Maybe you knpow them, maybe not...
1) Starved Rock State Park on the Illinois River near the towns of Oglsvie (sp?) and LaSalle/Peru. Great hiking trails through canyons (not normally associated with Illinois)if you have the time, and a lodge with good (though pricy) burgers. Good leg stretch spot on the way back.
2) New Salem near Springfield Illinois. A reconstruction of the town where Lincoln split logs, surveyed, and first studied law. Working blacksmith shop and a few of the actual buildings that Lincoln would have been in. A bit off the Highway, but worth the visit. Allow at least four hours, though. About half-way and there is a campground there if you wanted a spot for an over-night on the drive.
3) Cahokia Mounds on the Illinois side of the Mississippi but almost in St. Louis. A 14 acre Indian Mound over a hundred feet high that took almost 500 years to build. There's a fine museum/visitor center there as well as almost 100 other mounds and a celestially-oriented arrangement of posts, Woodhendge, that marked planting/harvest/hunting/etc. seasons. Right on the route and can be visited for an hour or a day - whatever time allows.
4) Hannibal Mo, just a little north of St. Louis on the Mo side of the river... Mark Twain's home town. Great Mark Twain Museum there, the actual homes of Huck Finn, Becky Thatcher and Twain himself - Tom Sawyer. The museum houses the original Norman Rockwell illustrations and preliminary sketches used in the edition of Huck Finn most of us are familiar with. Mark Twain cave is there and well worth seeing, as is a new one they just opened to the public recently that has, if I'm recalling correctly, at least 35 miles of known cave. Don't know how much is publicly accessible. Hannibal is a bit out-of-the-way for us but is worth an over-night stay if you want to see it with any kind of thoroughness.
There are lots of other spots that might be of interest - such as the graves of Mother Jones and her "boys", all sorts of caves, and Jesse James sites in Mo, for instance, but the ones I listed are my "top four". This is but one more reason why we need to keep going to these gatherings... too much to see while coming and going for just a single trip.
And those Ozark Rivers are sweeeeet, and the folks are the friendliest you'll likely meet anywhere.
Hardshell Kayak Sail Rigs
Kayak Motor Kit
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