The rest of the world has finally begun to catch up to the fact that Milwaukee is a city of considerable charm, liberal attitudes, and a zero-attitude, vibrant gay and lesbian scene. It's also site of the nation's largest gay pride festival, Pridefest Milwaukee, held in early to mid-June each year (over the weekend of June 7, 8, and 9, in 2013).
PrideFest takes place over a three days at a beautiful and centrally located venue right on Lake Michigan, the Henry Maier Festival Park at 200 N. Harbor Drive, just off I-794 and a few blocks southeast of downtown.
The Pridefest hours are Friday, 3:30 pm until midnight; Saturday, noon until midnight; and Sunday, noon until midnight. The top headlining acts this year are Sophie B. Hawkins and Andy Bell (of Erasure fame), who open the festival on Friday night; the Indigo Girls, who performs Saturday night; and Dangerous Muse and Amanda Palmer (of the Dresden Dolls), who will be performing Sunday night along with God-Des & She, the Dots, and many others. There are dozens of other performers over all three days. Additionally, there are dance pavilions, a health and wellness stage, an arts & culture pavilion, a Milwaukee Gay Arts Center stage, and a wide range of children's and family activities. Considering the caliber of performers, the cost for the festival is a bargain: just $13 for general admission on any particular day, or $30 for a three-day pass good for the entire festival.
Additionally, numerous gay bars as well as gay-popular restaurants, hotels, and shops have special events and parties throughout Pride Week. Check local gay papers, such as Quest for details. I've also included some helpful information about Milwaukee in my blog, TheCountyHunter.com. Also take a look at the excellent GLBT site produced by the city's official tourism organization, the Milwaukee CVB.