I did this trip with group of 5 others. 3 had never kayak camped before. 2 had gone on a few trips, to say the least. In mid October, highs were in the upper 50s, and lows in the low 40s. Not too cold, and not a lot of bugs.
The wind was constantly in our face all day, making it a bit of a struggle. We hit the 7 mile bridge around 3:30, a bit behind pace. Fortunately from there, the current picked up and things got moving. We passed through the canyon around the 10 mile marker and had no issues despite choppy wind.
Day 2 was a mixed bag. The water was calm in the morning, leading to a smooth paddle through the open lake area and then through the narrows and into the dells. We took our time going through the scenic dells, so hit the portage right at noon. We'd get back into the water around 2pm, after lunch and portage.
The portage takes forever, as you go uphill, through a big parking lot area around a power plant, then back down a hill. I'm happy to report that they've widened the last part going downhill, so it was much easier to traverse. There are clear maps marking the route, and signs along the way.
The second half of day 2 it began to rain and mist. This would last from 2-8pm, and eventually got us all wet and cold. We'd find a decent beach somewhere in the pine islands, around the 32 mile marker. Once the rain cut off, we were able to start up a fire and have some dinner.
Overall, it was a great trip. Nothing too crazy compared to previous trips. In October, there wasn't much speedboat traffic to contend with. The elements were a challenge, but nothing we couldn't overcome. The Wisconsin river can be a big challenge, but overall goes pretty smooth with its many islands and sandbars.