A Holiday Tradition Is Happening Once Again. The 75th Annual Santa Train Will Run It’s 110-Mile Route Through Kentucky, Virginia, And Tennessee. It Makes 14 Scheduled Stops, Bringing Toys And Goodies To Kids Along The Way. This Year, Bluegrass Music Legend And Appalachia Native Ricky Skaggs Will Be The Special Guest On The Santa Train. The Route Goes From Shelby County, Kentucky And Ends Up In Kingsport On Saturday, November 18th At 3 PM