The wind (or lack thereof) makes a huge difference.
I prefer a windless 0 degrees to 30 degrees with a 30 mph wind.
I grew up in far north-central Wisconsin, where (back in my day…) January highs were typically about 5-15F. Below-zero temps were common. But it’s all lakes and trees up there, so if you found yourself among the trees, the wind typically wasn’t bad. Out on a lake? yay, fun!
Madison has not nearly the density of trees, and campus is on an isthmus to boot, between lakes Mendota and Monona – it is very windy. So while at any given time, Madison was probably about 5-10 degrees warmer than my hometown in the tundra 210 miles to the north, it often felt at least as cold, if not colder, due to the wind.
My husband grew up in Madison. His family’s house was on Lake Mendota. His nickname in high school was “PT” for “part time” because he skipped school so much to sail and iceboat. He built his own iceboat.
I think it would feel much colder attending UW than U Maine!
I rented a dinghy a few times for some fun on Mendota. Typically, though, I enjoyed that lake by taking in the view from Union Terrace… while noshing a Paul Bunyan burger.
I still can feel in my bones all the times our Dad sent us out onto a frozen lake to check tip-ups. Probably explains why I shiver every time I see a small red flag . . . .
My husband taught sailing at Hoofer’s there. We went back for his 50th high school reunion in 2022 and ate on the Terrace. It was bleeping hot, though - close to 100.
We live in Boston and have bags and bags of those handwarmer things- we get value packs for feet, hands and a larger utility size (that I use when I have headaches).
I may be late to the party, but I would not take/wear hiking boots on college tours. It’s way too bulky, possibly uncomfortable, and you won’t be walking through snow drifts. A good pair of athletic shoes are all that would be needed.