We normally ride 4 or 5 days and have a general plan or loop in mind. I find it's better to be flexible because of conditions. Lots of times we'll book the hotel for the night when we're heading out for the day or when eating lunch. When we were younger and phones didn't get reception much, we'd kind of just show up in a town and hope for the best, or start calling places on the map when we're eating dinner. Ended up riding some long days doing that.
We're driving to the snow from IL/IN. Something we've done the past few years (before this no snow year) is have a starting point that doesn't involve as much time in the truck, and then staying in one place. For example a couple times we drove up to Tomahawk after work and stayed there, and rode up to Mass City and stayed there for several nights and then rode back to the truck the last day. We did something similar to the area you are looking at last March. I think we started around park falls and then stayed near Ironwood, WI. I can't remember which towns off the top of my head. This plan works well for us since it minimizes truck time and kind of lets us set up a base in the heart of wherever the most snow is and then do single day loops different directions from there. In NW Ontario on the other hand the way the trail system is set up, we'd be more likely do a multiple day loop with a different stop each day and set up the reservation in the morning before going.
Lots of different ways to do it. I don't like to be locked into a plan though because you lose flexibility if there's an area with conditions not up to what you expected. Earlier last season we drove up to Mass City and on the way we found out a buddy's kid could drive up from Traverse City area to ride with us a bit. Sounded like a great idea and it was nice to see him, but we had to ride all the way across the UP to meet him the Trout Lake area. There had been a big storm recently before then and there were several sections of the UP that had been beat up and not groomed which made for some riding we would have avoided had we not had to keep going the direction we were headed.
