Another ride in central Kentucky, taking place in the same area as the Horsey Hundred, is the Bourbon Country Burn on the last weekend of September. https://www.bourboncountryburn.com/#what
I rode last year and had a great time. Even though my legs were not prepared for the hills of Kentucky, the scenery, the horses, and the people made it all worthwhile. Also there was bourbon. My wife and I stayed an extra day to take in a couple more distilleries.


Crossing into Bourbon County Ky.