I went to school in Columbia and have riden much of the section between Rocheport and Jefferson City. October is a great month to hit the trail, especially with the trees in full color. Make sure to stop by the Cycle Depot in Hartsburg, and you can refuel with homestyle cooking at the cafe next door. Sipping some wine at the Les Bourgeois winery in Rocheport that sits on a bluff overlooking the River makes for a nice afternoon. And, If you like wine &/or beer, the German village of Hermann is full of wineries and brewerys. I believe the only way to experience a more authentic Oktoberfest is to travel to Germany!
This post is making me homesick!
"The bicycle is just as good company as most husbands and, when it gets old and shabby, a woman can dispose of it and get a new one without shocking the entire community." -- Ann Strong, Minneapolis Tribune, 1895