How far north are planning on? If you are coming up to the the start in MN the fall colors are in full swing usually early-mid October. We have had snow on Halloween and had snow on the ground, that stayed all winter, in early November. CGs up here generally close mid October, southern WI it tends to be late Oct.
If you were planning driving the entire length of the road you might want to consider starting up here in MN and WI and then heading south.
TT-2013 Passport 3220BH
TV-2004 F150 FX4, not exactly stock...
with 2001 Kodiak K215: 2010-10, 2011-12
with 2012 Grey Wolf 26BH: 2012-19, 2013-24, 2014-11, 2015-6
with 2013 Passport: 2015-13, 2016-15 booked