Originally Posted by
boomhauer
You might consider Herman, MO.
https://visithermann.com/
It's in the middle section of the Katy Trail (no hills).
Herman is probably the most scenic areas of the Katy Trail with large bluffs on one side and the Missouri river on the other.
There are also other rides you could take there if you want to enjoy some rather large hills.
This also looks like a possibility. Have good things about the Katy Trail. Most other seemed more like a few days in a direction, but this might work from here, hub & spoke style.