Back in 1890.

http://www.crh.noaa.gov/images/lmk/Tiger_of_the_Air/player/playershell.swf
Talks about the Louisville Tornado of 1890, but the map on Page 13 shows the outbreak in Western Kentucky. Which featured 2 F4 tornadoes, 1 F3 and another F2 across Western KY, another F4 touched down just to the east of Western KY.

- The main F4 tornado which may of been a family of tornadoes formed just West of Paducah, then cut across McCracken,Livingston,Crittenden,Webster,Mclean,Daviess. Another F4 formed in Marshall/Lyon County and struck Grand Rivers KY really hard. At least 30 fatalities occurred in these storms across Western Kentucky.