Since moving to Richmond we have been exploring all the side roads off of 421, haven't found that community yet though! I have figured out how to get to Livingston from the top of Big Hill, riding that ridge is really a good ride, have to keep alert though, lots of horses on the road
From the top of Big Hill you would have to continue on about 20 miles, then turn left by the old high school on HWY 587 to get to my area. I am on the south side of McKee. I know the Ridge you are talking about to Livingston, I've rode that myself many times and you are right, it is a beautiful ride. You can also cut over to Mt Vernon/Renfro Valley on that ride too.
Another ride you may like is 421 south to McKee, then left on 89 north to Irvine, then 52 back to Richmond (right on 89 south in McKee takes you to Livingston). Even better is 421 south past McKee, then HWY 587 north to HWY 1209. There you can turn left and go to Irvine, or right to HWY 399 which comes out on HWY 11 almost in Beatyville, KY. Then you could ride 52 back to Irvine (a must ride if you haven't rode it) or stay on 11 to Natural Bridge. This is an easy day ride, and fantastic scenery.
Red River Gorge, Buck Horn Lake, Laurel Lake, Green River Lake, Herrington Lake and Shaker's Village, Cave Run Lake, up HWY 68 (Paris, KY) to Maysville, KY then back down HWY 62 (Cynthiana, KY), Red Bird Mission School (HWY 66 in the heart of the Daniel Boone National Forest are just of few of the great day rides you have around you. You probably already know of these, and if so sorry to ramble, but I figured I'd throw some good ride ideas at you just in case.
I have two cousins, plus my best friend who ride with me, we all need to meet up sometime. We cruise, no hurry, and enjoy the day.