I have wanted to do this to and have spent about the last 5 or 6 years riding every part of the route at one time or another. There was a group that did this in Jan'01 from McHenry, IL to Superior and back. Not all finished. It took them 7 days. There was a nice article in the Illinois Snowmobiler Magazine shortly after they did it. I have traced their rout and modified it a bit up north since my sdestination would be St. Germain.
Here is my plan (starting point could vary from Wales, WI, Ocnonomowoc, WI, or Hartford, WI).
Day 1 - (Using Oconomowoc as an average starting poit between the 3 listed above) - Oconomowoc to WAtertown to Beaver Dam. Then scoot over towards Portage. From Portage head due north to Endeavor, Westfield, Coloma, and Hancock (Spend night in little motel in Hancock at Hwy 51 & V.
Day 2 - (I have done this part already just never been able to do it all at once) - Hancock to Wisconsin Rapids - Cross River in town called Byron. Then head to Junction City, then Edgar. Edgar to Merrill to Tomahawk to Harshaw to Lake Tomahawk to St Germain. This second day and the route I just described is 232 miles. This is also following the new high-line trail along 51 north of Merrill.
Like I said, I have ridden this entire route over the past several years, I have just not been able to put it all together. This has got to be a "drop what you are doing and do it" type thing when all of these counties are open andhave rideable snow. That is the hard part.
I have heard of pople riding from West Bend to St Germain in one LOOOONNGG day. But they took a more easterly route and use some RR bed type trails. I figured as long as I got into a familiar area up north around dinner time, I could do that too from West Bend.
Carry extra oil (unless you have 4S) and after 50 miles get gas when you have the chance. Chase vehicle is noce. I had one when I rode Hancock to St Germain and met the driver for unch in Merrill then met him at St. Germain. I made contact mid-morning, of course at lunch, and then mid/late afternoon once I was north of Tomahawk.
This would be a blast. Good luck. See if you can find the article. Coemeto think of it, I may still have that issue. My dad who lives in IL gave it to me. I saved it as reference to this trip. If I find it, I will try to let you know what exact back issue it is.
Kevin
...just sayin