The Santa Train Is Getting Ready To Make Its 75th Running From Shelby Kentucky To Downtown Kingsport Next Month. This Year’s Special Guest On The Train Will Be 15-Time Grammy Winning Artist Ricky Skaggs. He’s A Kentucky Native And Will Be Helping To Hand Out 15 Tons Of Toys, Food And Warm Clothing During The 110 Mile Rail Route. The Event Happens On November 18th.