BikerBoy from Maryville, IL on 8/10/2020 12:31:23 PM:
The first week of October is one of my favorite times to ride. The leaves will probably not have started changing by then, but the air is crisp with low humidity -- perfect for biking. Pilot Grove is a wonderful small farming town. Very laid-back and safe. I would just make sure the police department (or Cooper County Sheriff) knows that you are leaving your car there, so it doesn't get towed. You could also talk to Jerry at the Katy B&B across the street to get his opinion. He was a former policeman.
Campgrounds have all still been open in October when I have ridden in years past. But best to check first since nothing is normal in 2020!
If we get a lot of rain, you might plan on ending in St. Charles, as the rest of the trail to Machens would be impassable.