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
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.