Have you been to Owensboro? Their waterfront is just lovely and the park is one of the best in KY for sure! During the warm months, they host "Friday After 5" so that everyone can come down to the gorgeous waterfront park and enjoy family fun and live music! The fun spans 8 blocks in Smothers Park and it's all free!
It all starts at the end of May and goes through early September.
The full schedule can be found here: http://fridayafter5.com/events
You can download a printable schedule so you can have it handy. They touch on so many genres of music, it's impressive!
In addition to the live music, they have other live entertainers, children's events & activities, vendors, and contests for kids!
Here's a video that shows what it's all about - note, I did NOT pick this thumbnail image!!!!