In what sense is Madison "incredibly unique and cool"? I would say a city with beautiful natural scenery like Sedona or beautiful architecture or special culture like the Amish counties as unique and cool.
I've never been to Madison, but the sense I get is that it's a college dominated city with a very rich countercultural history and the cultural institutions to match--lots of bookstores, independent music venues, artist collectives, etc. Similar to a smaller version of places like the Bay Area, Austin, Seattle, etc. though I'm sure gentrification continues apace in Madison as it does in similar places.
Madison also has a unique location between Lake Mendota and Lake Monona, which gives it a pretty unique physical character. It also has quite a few Frank Lloyd Wright buildings as well.