@tadoerner Great question!
We reached out to our team in Cincinnati and did some digging online as well and came up with a couple of suggestions for you. Additionally, @CarlR just asked a similar question in their post, Looking for a good multi day hike in Kentucky, so we thought we could connect them here as well as there is a lot of overlap. Here is what we came up with:
- Daniel Boone National Forest. Just over 2 hours away from Cincinnati.
- Red River Gorge Geological Area. Also right at the 2 hour travel time mark.
- Cumberland Falls State Resort Park. Just under 3 hours from Cincinnati.
- Jefferson Memorial Forest. Not a lot of length, but you could combine some of these trails. Less than 2 hours from Cincinnati.
- Sheltowee Trace National Recreation Trail. 319 mile trail that runs through some of the above mentioned locations.
Hopefully this helps, don't hesitate to come back here in the community and tell us about your adventures!