I’ll be visiting Wilmore (just outside of Lexington) for about a week to see my mother, and I was wondering about what to see, eat and drink while there. I considered taking the train but unfortunately Amtrak doesn’t go near there, so it looks like I’ll be flying from Portland to Lexington.
Lexington puts you right in the heart of Kentucky’s Bluegrass country. Plan your trip around horses and bourbon.
I could do worse. 
Elaborating on the horses-and-bourbon theme, the Kentucky Horse Park has live horses, summer events and BreyerFest, if you or someone you know is into model horses. Nice place.
If you rent a car you can follow the Bourbon Trail. Bardstown is sort of the bourbon epicenter of Kentucky.
The Blue Door Smokehouse in Lexington is highly rated for barbecue though I have yet to try it.
Strangely enough, I’ve been to Wilmore. Long story but my (then very young) niece called it “Lawn Mower, Ky.”
I’d like to check out the moonbows south of there if you can.
And while you’re at it, some other ideas:
Don’t go to Harlan…you’ll never leave there alive.
Stranger
If you like live music, and you are in or near Lexington, you could check out the Big Band and Jazz Series which by August is in Ecton Park. That’s on Tuesday nights. (For my taste, most of the big bands or concert bands are pretty great, but some of the Jazz ensembles late in the summer are forgettable).
Thursday nights there is Southland Jamboree-- Bluegrass Music, concert followed by a jam session at Moondance Amphitheatre in Beaumont Center. (That one usually has food trucks available).
If you like Caves, Mammoth Cave is worth a visit. (Disclaimer: it’s at least two hours from Lexington and there’s a time change involved. Also, make sure you investigate tickets for cave tours in advance–I think the most basic tours don’t neccessarily fill up, but longer more involved ones might. Also, that’s a National Park and it’s popular).
If a cave with fewer people would make you happier, Carter Caves State Park is worth a visit. (Although . . . it’s significantly closer to my house, but not neccessarily closer to Wilmore than Mammoth Cave is).
Shaker Village in Harrodsburg might be worth visiting.
The UK Arboretum is worth a visit-- if you want a nice, paved path surrounded by flowers and/or trees. That’s free.
Bernheim Forest Giants is cool-- I’m not sure how much driving you want to do. (It’s a bigger, more sprawling arboretum, which presently has 3 giant trolls made from reclaimed lumber.)
If visiting houses formerly lived in by famous people is your thing, your might check out the Henry Clay Estate(Ashland), Waveland, Mary Todd Lincoln’s Childhood home, maybe more.
If Civil War history fascinates you, you should visit Camp Nelson There’s a national cemetary (Think Arlington, only smaller and less well known), and also some history of Camp Nelson which was a supply depot for the Union during the Civil War.
I’m looking forward to visiting the Bernheim Arboretum/Forest, but not for the trolls. 
They have interesting things going on. I can however experience Firefly Fridays at my own place (the show has been near-spectacular this year).
Kentucky in August…Eeuuwww.
I don’t “do” humidity at all, so Kentucky and I didn’t get along in August. I say that Kentucky is absolutely wonderful for fifteen minutes in the Spring, and twenty minutes in the Fall.
The people in Kentucky were fantastic. I couldn’t get over how nice everybody was! I’m from California, and I spent the first six months in Kentucky almost biting my tongue off. People were so nice, gracious, and welcoming, my California attitude wanted to say, “What do you want?”
I actually enjoyed our time in Kentucky. It was Mr VOW’s last duty station before he retired from the Army.
~VOW
Jim Beam Distillery in Clermont (just south of Louisville) has a really nice tour; the tour guide we had several years ago really liked her job – I mean really liked her job.
There are free samples at the end of the tour. 
True enough, but August tends to be similarly steamy in much of the continental U.S. and along the eastern seaboard and Gulf Coast.
I don’t think John Sebastian had Lexington in mind when he wrote these lyrics:
Hot town, summer in the city
Back of my neck getting dirty and gritty
Been down, isn’t it a pity?
Doesn’t seem to be a shadow in the city
All around, people looking half dead
Walking on the sidewalk, hotter than a match head
The trick is to make sure our parents have a nice mountain cabin by a lake for our August visits.
Mammoth cave is said to be very good to visit
Can you escape for an overnighter?
Visit the Corvette Museum in Bowling Green, and then visit Mammoth Cave (or vice-versa).