Jerry Whittle from Belleville Illinois on 9/2/2020 1:07:49 PM:
I've ridden both directions 4 times and concur with Mark that west to east is best. One other advantage is that many businesses on the trail are closed on Mondays and Tuesdays. However there are plenty of open places in Sedalia and Boonville. So if you start from Clinton on a Monday morning, it isn't an issue especially if you stay in both towns. Even if you go straight to Boonville, that mitigates the potential problem.
However there is one disadvantage of going that direction. If you get on the trail early, the sun can be in your eyes. Make sure that you have good sunglasses.