My best friend and I took a long weekend and went to Hermann, Mo for Octoberfest. It was a bit chilly so we didn't ride nearly as much as we had planned. We did manage to hit the trees just right. They were beautiful. The opening pic is along the Katy Trail near Rocheport, Mo.
In Hermann, we ended up at a "work in progress" B&B (house from the 1880s) with a rather stressed and very vocal inkeeper where our room had a clawfoot tub and no shower! We had a great time but learned Octoberfest is NOT when you want to visit the German area of Missouri. The lodging is pricey and difficult to find last minute, things are a bit more rushed, and locals say overall prices are much higher.
We felt maybe there were too many party types in town for our taste. September would be our suggestion.