As far as I can tell, all Sumner County school children are taught that Pilot Knob is so called because riverboat pilots used it as a guide on the Cumberland.
Pilot Knob isn’t on the Cumberland. It used to be taller, before it was quarried, so possibly, it used to be visible, but, even if that’s the case, there’s a bigger problem with this explanation.
Pilot Knob was called Pilot Knob long before there were riverboats on the Cumberland.
Thanks to Google Books, we now have a plausible explanation.
From The Historic Blue Grass Line:
From this camp Station Camp Creek got its name [Mansker, Bledsoe, Drake, Gillespie, Cage, and Franklin had a semi-permanent hunting camp here], and Pilot Knob, on the north, was so called because it guided the hunters through the wilderness to and from their main headquarters, or station camp. (Note.–Pilot Knob is mentioned in a road-making order on the minutes of the Davidson County Court, 1786, p. 109.)
Now, this seems right to me. You want to be able to find the same dry place year after year, you find one near a great big hill standing alone visible from the old animal trace you’re using to get into the area. You want to easily be able to get back to your base camp after a long day of hunting? Again, put your camp near the big lone hill.
But, like I told C., I wouldn’t be surprised to learn that there was a sailor among the long hunters, hence the reason we’re seeing these ship terms.