Re: Does a first sail ever go as planned?
Welcome to the lake!
I was aboard one of those other sailboats; major regatta, the Commonwealth Cup, sponsored by the Commonwealth Yacht Club. Another option is the Kentucky Lake Sailing Club.
I highly recommend one or the other; great groups of fellow sailors. Plenty of friendly people to advance your learning curve; try out your sailing chops in a race, maybe even catch a crew spot on someone else's boat for some advanced learning.
Fair winds and following seas!