You should ride from Williamsburg to Lake cumberland along 92 a very beautiful and curvy road. It crosses Big South Fork, goes by the train museum in Stearns then goes all the way right into Lake Cumberland at Beavercreek Resort outside Monticello Ky. Then on the way back go up 90 to Burnside then south on 27 to 90 EAST to go by the Cumberland Falls another curvy road with a lot of beautuful scenery and plenty of places to pull off and take a break.
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