What part of Kentucky? It took us about a week to ride across the state. FWIW, it took us a bit over a month to get from western Kentucky to the middle of Colorado.
From Steamboat Springs, you have a short jog to Kremmling to pick up the TransAm. Note it goes south past Breckenridge to cross Hoosier Pass, then a long-ish day to get down to Canon City. If you're in Steamboat, you should have a better idea of weather and snow on the passes in early November than I do. From there, you're on the high plains in late autumn / early winter.
FWIW, the Missouri Ozarks were the second hardest part of the TA for me, only behind eastern Kentucky. If you catch that ride to Fort Collins, you might consider making your own route east to pick up the Katy Trail, then cut south to pick up the TransAm near Kaskaskia.