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The first year I did it, it was hot. It was the first real hot day of the season so myself and others weren't acclimated and suffered. Last year it was beautiful the day before but a front came through and it poured all night, up until the race start. Start was delayed. People were turning in their timing chips because they didn't want to deal with the weather on the bike. Transition was a mud pit. However, temps were on the cooler side so the run was pretty enjoyable.
As for the race itself, the venue is nice. Parking is across the street at the Aliant Center and you can take a shuttle right to the start. If your family plans to come along have them pack a lunch as there is no food options available. The venue is a couple of miles from the downtown Madison.
Swim: it should be wetsuit legal. Last year the swim was in question because of bacteria but they got it cleaned up. It can be choppy it it's windy. Up to the first buoy it's pretty shallow. Otherwise it's straightforward.
Transition: it's in a field so if it's rainy be prepared for mud.
Bike: Starts out pretty flat but after about 10 miles the hills start and they never end. It's a fairly technical course and there are several times you'll be going downhill and then turning into an uphill. If you don't get the chance to ride it, then I'd suggest driving it the day before. Road conditions can be crappy, but typical by Wisconsin standards.
Run: I actually like the run. It's a big loop around the lake with a small out and back in the first and last mile. Lots of shade and the residents will be out cheering you on with sprinklers and water guns. Last 2 miles are so are unshaded and can be hot. Some hills but nothing horrible. There is one uphill just before the finish that's pure evil but by then you're so close to finishing.
Weather wise, I'd be prepared for anything. Overall it's a good race and a lot of people use it as training for the full.