Hi @CarlR - Thanks for reaching out! Kentucky has so much great land to roam around. It's great to hear you're planning a trip.
From my time in the Red River Gorge I know that people love section hiking the Sheltowee Trace Trail. In total, the Sheltowee Trail is 323 miles, but sections 12 and 13 (on the map on the site linked above) take you along the Red River and are right around the distance you're looking for.
Another good option is the Ridge Trail in Cumberland Gap State Park. It is a neat 21-mile trail that hugs the top of the Cumberland Ridge. While it is a well maintained trail, there were not blazes to follow the last time I was in that area. You might want to contact the park to know what to expect in regards to navigation. If you do head that way, be sure to stop by the impressive sand cave! It shouldn't be missed.
Let us know if you have any more questions and we'd be happy to help. Happy hiking!
When I first read your post, I had (in my mind) a great idea - hiking the bourbon trail! I mean, you could trek along and not have to worry about indulging a little too much and then getting behind the wheel nor would you have to worry about consuming all those extra calories because you'd be burning them off.
Sadly, I couldn't find any such established path. ☹️
But if anyone knows of a way to hike/backpack the BT, let me know - I'd make the drive to Kentucky for that!
@Philreedshikes Well now this is a thing that has to happen