CotS! CotS! CotS!
Concerts on the Square is one of my favorite things about Madison. Wednesday nights in the summer the Madison Chamber Orchestra puts on a FREE concert on the capitol square. Most people put out a blanket and bring a picnic. Wine and beer is allowed as well.
If you are there for the music you can get pretty close as long as you get there early. But concert goers spread out across the majority of the square and socialize a lot as well.
It's a great event for people of all ages.