I'm going to come right out and say it. Milwaukee is fabulous.
If you're one of those people that bemoans the idea that there isn't enough culture here, or there isn't enough to do, then you CLEARLY aren't utilizing your city to the fullest. Pound for pound, Milwaukee is one of the coolest mid-size cities in the country. If you think you need more, then move somewhere bigger. Meanwhile I'll be enjoying "the city of festivals", the pristine lakefront, the beautiful architecture, gorgeous parks, and all the good eats...
As with any urban center, downtown is where most of the action is. The best online resource for maximizing your Milwaukee is MILWAUKEE DOWNTOWN. Click on the link below to visit their website, and I encourage you to sign up for their emailed "HOTLIST", which will keep you abreast of all the festivals, functions, theater, concerts, and cool goings-on. This weekend we have Arab World festival, and next weekend you can check out River Flicks at Pere Marqutte Park and Irish Fest, which is the worlds largest Irish cultural festival.
If you're bored, don't come crying to me!