Kentucky sometimes gets a bad rap and I'm not sure why. It seems to me, the Bluegrass State has one of the richest regional identities in the union. It gave the world bourbon. It gave the world Bill Monroe, the father of bluegrass music (no relation to Burt); Wendell Berry; Abraham Lincoln; and, most importantly, the Hayden family. It also has some great roads that wind through the hills and trace the rivers and creeks.
Kentucky state Route 499 and KY 52. Route 499 makes its way to route 52, where it enters Daniel Boone National Forest. Pull up a Google map and check out all the twisty roads through the national forest. Roads that parallel creeks and rivers tend to be good ones. The Daniel Boone National Forest has a higher than average concentration of crooked creeks and winding roads, so there are plenty of small side routes to explore. Red River Gorge in the national forest is a big draw for hiking and rock climbing, so look out for slow-moving Subarus.
Stop by historic Boone Tavern in Berea. Their famous yeasty rolls are worth the trip. Also, they serve bourbon.
After lunch, swing by Berea College. It’s a badass little school. Berea was the first non-segregated, coed college in the south. The college went all the way to the Supreme Court when the Day Law of 1904 prohibited black and white students from attending the same schools. Berea was founded with the goal of providing students of low economic means a way to receive higher education; today the college still ensures all of its students’ financial needs are met. Pretty cool. Way to use that endowment for the common good, Berea. No matter how you look at it, it’s both progressive and conservative—very Wendell Berry. Lead on, Kentucky.