Where in Kentucky do you plan to settle? The Louisville Bicycle Club is very active and puts on several rides each day. I know there is a cycling club in the Lexington area (Bluegrass Cycle Club) but I've heard through the grapevine they currently are not very active.
If you are going to be in the area in Sept. I would highly recommend the Old Kentucky Home Tour. This year I believe it will be held Sept 13-14. You will have several options on the first day - a 50, 70 and 100 mile routes to choose from. The SAGs are wonderful and the lunch stop in Fairfield is excellent. The second day is a 55 mile route and the cookie stop is awesome. Both days will take you through some beautiful countryside (you will travel through Jefferson, Bullitt, Nelson and Spencer counties).
I live in Shelbyville, Ky (half way between Louisville and Lexington). Feel free to contact me.