Bourbon Trail--Lexington, KY
It's been a while since we did a bourbon tour but one of my findings was, don't eat at the distilleries. The food isn't that good.
I would suggest Wallace Station in Midway. It was featured on DD&D and is a great place. Right on the edge of bourbon country and in the heart of horse country. The drive is worth it alone. Try the East Hampton sandwich. It's great.
In Lexington The Parkette Drive In is really cool. The original KFC if you will. The owner sold the name Kentucky Fried Chicken to the Colonel back in the 50's.
Some terrific eats to be had there.
I'll second DT's advice--don't eat near the distilleries--we ate at Wallace Station last fall and enjoyed it. Good beer selection for a place its size. (We always go to the DD&D places if there is one nearby) Also at a little place on the main drag in Versailles (west side of street) that was great for lunch and good value dollar-for-dollar.
Parkette on New Circle Rd (Lexington)is such a classic restaurant--like stepping back to the 50s/60s, and was also recentlyfeatured on DD&D.
If you're going to Heaven Hill, check out Bardstown eateries, altho our vist to the historic Talbott Tavern for lunch was forgettable.