Great ideas and thanks for them folks.
Fred - This would be my fifth time out. I am a 61 year old former smoker, free for almost four years. I can spend many hours in the saddle. I plod at 12 MPH and can easily average 60 - 70 miles a day. I have completed one century fully loaded, but that is the limit. I would do centuries on the plains if needed, but no longer need to meet that goal in life. Been there.
It is the slogging upwards in the mountains I have no experience with and would like to get a handle on that. Your suggested 35 miles increasing to 60 is useful. I will be in touring shape at the start.
commuter - I am about 60 miles east of you in west central Wisconsin. Like you, there are no mountains near here for me to test my long climbing style. (BTW- My daughter attends Hamline University in St. Paul.) Your idea of jumping on the train is great. I will be under some sort of timeline and already know that 3 to 3 and a half weeks for the total trip, out, a night or two with my brother, the ride and the return transport is allotted time.
indyfabz & johnsondasw - Your comments lead me to believe that the ACA maps suggested by Fred would round out many of my questions relating to overnights and supplies etc. From there, figuring out when I could jump an Amtrak home should allow me to flesh out a trip itinerary.