Milwaukee 

Milwaukee – a city defined by an unusual blend of chic and casual coolness.  Comfort and ease exist side by side with exciting amenities and a progressive attitude to create an unbeatable, gay-friendly destination.
Selected as a "Surprising Gay-Friendly Destination" by PlanetOut in its 2008 Travel Awards, Milwaukee is home to a number of organizations and annual events that celebrate the LGBT community. 

Events / Organizations

For three days each June, the nation's biggest Pride entertainment lineup assembles for Pridefest along the shores of Lake Michigan at Henry Maier Festival Park. Here, thousands of festival-goers gather to enjoy world-class entertainment, sample some of the best food the city has to offer and stroll through the marketplace.
http://www.pridefest.com/

In the fall, the city welcomes the LGBT Film/Video Festival, now in its 22nd season.  This 11-day event showcases work from around the world by, about and for the LGBT community. 
http://www4.uwm.edu/psoa/programs/film/lgbtfilm/   

Opened in 2005, the Milwaukee Gay Arts Center in the Walker's Point neighborhood provides a venue for LGBT-relevant visual and performing arts. The Center also provides arts-related educational opportunities.  
http://www.milwaukeegayartscenter.org/MGAC/Home.html

Neighborhoods

Walker’s Point serves as one of the main gay residential areas in the city and hosts the majority of gay nightlife hotspots that range from mellow dive bars to full-scale nightclubs. Dozens of old warehouses in the Historic Third Ward have been converted into amazing lofts, art galleries, chic cafes and stunning lounges.

Where to Stay

With five TAG-approved hotels, and new projects and renovations continually popping up, Milwaukee's variety of gay-friendly accommodations (including boutique hotels and Bed & Breakfast options) is sure to impress.

Visit Us Soon

Come to Milwaukee: a gay-friendly city combining top-flight attractions like the Milwaukee Art Museum, Discovery World and the Harley-Davidson Museum with a vibrant arts scene, pulsating nightlife and sassy shopping. You’ll discover a welcoming city of lakefront festivals and award-winning parks, along with eclectic neighborhoods for adventurous foodies to explore.

Milwaukee—if it happens, it’s here. With so much on tap, your getaway will be nothing short of unforgettable.

    

Other sources of information:

Milwaukee LGBT Community Center - www.mkelgbt.org 
PrideFest - http://www.pridefest.com/