I'm guessing that you are referring to US36 and not Kansas 36 .... I took that west across Missouri & Kansas to InZane back in 06. It is a nice road some parts are very scenic and the people I met were great. Going from West to East I am sure will be more scenic simply because eastern Colorado & western Kansas are really flat. So as you head east the scenery will improve. Not very many twists or turns but there are a few dips (the Kansas curves go up & down .... not side to side

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How you getting from US36 to Madison or Milwaukee? There are a number nice roads through Iowa & Illinois. If you are coming through Missouri I would suggest heading north through Iowa along the Mississippi and cross over to Illinois around Dubuqe and take US20 into Galena. From there you can find any number of roads to take into Wisconsin and through the rolling hills and fields to Madison or Milwaukee.
If you have an idea of when you will be coming through give me a shout and I will try and hook up.