catfish

i did a similar tour a few years ago Started in august. i took the train from Wisconsin to Portland then headed to the coast and took the T A route east; When i got to Montana my plan was to hit "going to the sun hy" and do Glacier park again from the opposite direction Id done it previously. then hop on the northern tier route i caught a weather report of snow in the pass so I went just below G T S Hy . Eventually I headed north and got on the northern tier route. The winds in north Dakota were brutal! .Most days were warm fall days The nights were cold Sometimes it rained and some times it sleeted. Occasionally I had some snow. When i got to Wisconsin in the colors were spectacular so I headed north and rode to Eagle River then south to home. Being so late in the touring season i many times thought I had to be the only guy left out on the road then just like that, i would run into another touring cyclist

All in all it is doable the first part the weather will be nice and mostly warm nights later in the higher altitudes the nights will be cold in the tent. Sounds like you got the time have a good sleeping bag and deal with whatever comes your way best of luck to you

Where about in WI are you headed back to?
Catfish