Clues to a Future Hike

The other day, I wrote about a future backpacking trip I will be planning, and how the three of us had to come up with an idea for a trip.  I think we have finalized this now, so here are some clues about where we are going.
1.  This hike is in the state known as "The Mother of Presidents," since four of the first five US Presidents were born there.
2.  The circuit hike is fairly near, just west, to a city that was originally known as "Big Lick."  We might even be able to see this city from some of the mountains.
3.  That's right - mountains.  This hike is not at the coast.  We'll be gaining and losing nearly 8,000 feet over the 36 miles of hiking.
4.  Despite the name given to this hike by some, Secretariat, Seattle Slew, and War Admiral never ran here - as far as I know.
5.  The name referenced in #4 is a result of three spectacular view points along the hike.
6.  A goodly portion of this hike occurs on the most famous long distance trail in the US of A, the one marked by white blazes.  It runs from northern Georgia to northern Maine.
7.  We likely won't find a dragon on this hike, but we may find one of their teeth.
8.  One of the most famous views on the entire trail mentioned in #6 occurs on this hike.  Backpacker Magazine, in a recent issue, rated it as the best outdoor vista in the state referenced in #1.
9.  The last part of the hike as we return to our car and complete the long loop is called the North Mountain Trail.