door county triathlon - how big is this bluff?

Dont worry about it.  Its just a really short really steep hill.  If I had to guess the steepest part is probably 1/4 mi long and ascends 75-80 ft.  I think the whole hill is around .4 mi and around 100 ft ascent.  All you gotta do is take short steps and youll get up it alright.  Also, be prepared for a short hill after the initial descent.  Its one of those tricky hills where you get up the worst of it, you think youre done, but then road curves and theres another short climb.

I dont leave in Madison, so I cant really compare. But if you want to start training hills, just hop on some shorter steeper hills and youll be fine.  Check out the elevation maps on the dc tri site too.