You might want to skip the Monroe Park, there is music there only a few times a year. The drive may not be worth it.
However, if you are looking for music Closer to Lexington try a night a Renfro Valley down I-75 at exit 62. They have something going every day of the week.
1994 Vectra DP
230 Cummins / MD3060 Allison Trans
Banks Stinger / Improved Injectors
US Gear Exhaust Brake
Towing 1989 Ranger / Unified Tow Brake
Georgetown is located just a few miles north of Lexington. We toured the Toyota plant there one year. Might check to see if tours are still offered - best to book ahead if interested.
2007 Holiday Rambler Admiral 30 SFS with lots of good stuff!
Come down to Somerset and visit Lake Cumberland if you like boating, golf, good food, hiking, etc. There is a Civil War battlefield park close by with a museum as well. About 80 miles due south from Lexington on US 27 or by I-75 a little longer.