re: Trip to Lexington booked need your opinion

definitely plan on hitting Keeneland one day. It is a great time, weather should be great.
A couple good steak places - Jeff Ruby's opened downtown and Malones in Landsdowne. Old school steak house downtown is Columbia's.
Dudleys downtown is very good, Carsons and Coles 735 are good as well.
A few low key places in Chevy Chase - Bourbon & Toulouse (Cajun), next to Chevy Chase Inn, best dive bar in town, also Charlie Browns, Bear & Butcher and Josies- good breakfast/ brunch.
Merrick Inn good old style club restaurant, great patio, bit of older crowd.
Good pizza - Joe Bologna's on Maxwell, its in an old church.

In addition to the bourbon tours, the horse farms also offer tours, Claiborne, Lanes End, 2 of the bigger ones, both have Derby winners standing stud. Also the Horse Park is pretty neat and has a complete history of the horse not just racing, but has several exhibits about racing in Ky.