Star Events (StarEvents), Chicago

For the first time ever, Chicago Pride Weekend will kick off with the Pride 5K and party, but this isn't a traditional race. While most 5Ks feature t-shirt clad runners jogging around bright and early, this race kicks off as the sun sets over Lake Shore Drive. The dress code is also different; participants here don their sexiest, skimpiest outfits for a run that's less about winning and more about showing off the goods. Everyone's encouraged to register and attend the after-party with a +1. Whether they're coming with a date or scoping out the scene with a wingman, participants will fill the route and party at Diversey Harbor with twice as much fun as usual.

Guests receive two drink tickets for the harbor party, where DJ Adam LeBlanc from Sixteen Candles will pump up the crowd before an after-after-party at D.S. Tequila. Participants will look great in limited-edition T-shirts designed by local artist Borris Powell (included with registration), and can feel great about the cause—the LGBT Senior Center is a joint project of Center on Halsted and Heartland Housing, and is slated to open in Boystown later this year.