The vast majority of the bars and lounges in the dynamic university and political city of Madison are gay-friendly - this outdoorsy, progressive, and well-educated community that straddles Lake Mendota and Lake Monona is one of the best small cities (the population is around 225,000) in the country for gays and lesbians to live in, with a terrific Gay Pride event held each August. It's not a gay-bar hub the way Milwaukee is, but it's only a 75-minute drive there, and Chicago, with one of the nation's largest gay scenes, lies only a 2 to 2.5-hour drive away, too. Having said that, the city's gay nightlife scene has improved quite a bit in the past couple of years.
Madison GLBT club crawlers will find a few fun gay Madison hangouts, plus a number of gay-friendly lounges, coffeehouses, and restaurant bars. When I last visited Madison, I kept hearing talk that a new club was set to open downtown. After more than two years of searching for a suitable location, in August 2009, Plan B (924 Williamson St., 608-257-5262) opened along already hip Williamson Street, a 15-minute walk northeast of the Wisconsin Capitol grounds. By all accounts, the slick dance bar and video bar has garnered quite a following with gay guys, lesbians, and more than a few GLBT allies in Madison. A variety of events keep the place interesting, including noon T-dances the first Sunday of each month, Monday sing-alongs to musicals, 18-and-over Thursday dance parties, and bimonthly women's parties on Friday nights called "Cake."
Madison has two other gay bars downtown, the cozy neighborhood lounge, the Shamrock Bar (117 W. Main St., 608-255-5029), which opened in 1985 and draws a mostly male (thought it's very female-friendly) bunch of all ages, from students to long-time locals, and the newer (opened in 2008) Woof's (114 King St., 608-204-6222), a sports-themed hangout that cultivates more of a following among players from GLBT sports teams as well as bears, leather daddies, and the like. Both of these spots enjoy a convenient location just a block from the Wisconsin Capitol grounds, and a 10-minute walk from the University of Wisconsin campus.
Prior to Plan B opening, the city's top gay nightlife choice was the quite large but out-of-the-way Club 5 (5 Applegate Court, 608-277-9700 or 877-648-9700), one of the Midwest's most substantial gay entertainment venues. I haven't visited since Plan B opened, but I've heard some reports that Club 5's popularity has waned a bit as a result of the new competition, while others stay it's still drawing big crowds, especially on weekends - recent remodeling of different parts of the club have helped, no doubt. Club 5 comprises a large disco and lounge, a patio that's good fun in warm weather, a lesbian lounge called G.Bar, and a leather-and-levi's and bear bar called the Barracks. In other words, there's pretty much something for everybody at Club 5, and the crowd offers a good cross-section of Madison's gay scene: students, men, women, professionals, working-class types, academics. The drawback to Club 5 is that in this walkable, compact city, you have to drive or take a taxi to get to this facility about 4.5-miles south of downtown, just off the U.S. 14 freeway. The setting, near fast-food restaurants and strip malls, isn't especially inviting either, but once inside, you'll discover a nice mix of people and a highly welcoming staff.
As for gay-friendly, mostly hetero hangouts, Madison has many. Back downtown, next door to the Shamrock, you'll find the Tornado Room (116 S. Hamilton St., 608-256-3570 is a retro-fabulous lounge, aglow in dim-red lighting, that's attached to the Tornado Steakhouse. It's a fun option for late-night cocktails or food, and you'll often see gay folks in here, having sauntered in from the Shamrock. The Tornado is justly famous for its tender steak sandwich, served au jus with sauteed onions and horseradish cream.
Stroll across the Capitol grounds and you'll pass a couple of Madison's best restaurants, Harvest (608-255-6075) and L'Etoile (608-251-0500), which are at the corner of N. Pinckney and E. Mifflin streets.
As you might expect of a city with a lively collegiate and arts scene, Madison has plenty of inviting coffeehouses. Among the most gay-popular, drop by Michelangelos Coffee House (114 State St., 608-251-5299), along the bustling downtown State Street pedestrian mall. It's close to dozens of shops, restaurants, and cultural attractions. Another excellent option, with a strong following among lesbians, is A Room of One's Own Feminist Bookstore and Coffeehouse (307 W. Johnson St., 608-257-7888), which is on the corner of the State Street mall and carries a fine selection of books and periodicals.