Can't believe i'm the first to post in this forum! Kentucky is where I'm from, and although I don't live there now, I love talking about all the great things there are to see and do there, and really enjoy getting to do them when I travel back. Like:
Louisville! It's one of my favorite cities on Earth - and I've been to more than 35 countries! The restaurants, the vibe, the relative ease of getting around downtown by mass transit, the walkability of "the Highlands", the parks, Actor's Theater of Louisville, Shakespeare in the Park, the general vibe of the city... it's really wonderful.
Bardstown, Bourbon capital of the world! Great distillery tours (Maker's Mark is one of the best)
Audubon State Park in Henderson, Kentucky: great museum of Audubon prints, beautiful hiking trails, decent campground (and cabins!)
The WC Handy Blues Festival in Henderson, Kentucky: world-renowned and FREE. Every summer.
AppalShop: a cultural center in Eastern Kentucky that produces music, theater and other art from the region.
Mammoth Cave: one of the first UNESCO world heritage sites. Massive cave system!