It dawned on me one day what makes Milwaukee so cool.
In short, it's big enough to have lots of cool stuff -- but small enough that the cool stuff is concentrated in a relatively small area.
I used to regard this as a shortcoming. I love to wander cities on my bike, and it seemed like Milwaukee just didn't offer all that much territory that was worth wandering about in. By the time you hit West Allis, you've reach the end of the interesting stuff. The northwest stretches on for mile after boring mile. The south is fascinating in its diversity and vital struggling immigrant growth, but it's pretty finite, cut off sharply at 35th Street and more dully around Oklahoma.
But what you have left -- the East Side, downtown, Riverwest, KK and Bayview, and above all the lakefront -- are just packed to bursting with interesting things and people.
Consider an evening in September. I stopped at Bradford Beach to watch volleyball and parasurfers. I biked past hundreds of docked boats at the marina, in all sizes and degrees of extravagance. I stopped to watch a rugby team practicing. I then followed the sound of bagpipes to find a troop of bagpipers rehearsing. As I watched and listened, a tall ship sailed past, while a tech school class learned surveying techniques, and a parade of walkers, joggers, and bikers passed by, and the sun set in fiery colors behind the downtown skyline.
Where else can you find that much going on in such a small space?! Where else?!