Starting from the north, and working south, is a more doable trip. Work south until you run out of rideable snow conditions, then work back north. Using different routes each direction. The trip starting in the south, and working north, then back south, would take several things to be doable. First, the northern 2/3's of the trip would have to have good existing snow pack depth. Then you need a large, heavy snowfall, storm to dump good, and deep snow on the southern 1/3 of the trip. This could maybe make the round trip possible. Again, different routes each direction. Sign me up!!!!!!!! I would like to start at the southern Wis boarder, possibly in No Ill.