Headdress Balls have been held at Walt Disney World's Swan and Dolphin Hotels, The Rosen Hotel, Universal Studio's Royal Pacific Hotel, and The Omni at Champion's Gate.
This year's 20th Anniversary Ball was held at the new Hilton hotel on International Drive on October 3rd, 2009 and was co-chaired by Sam Ewing and Brad Grosberg.

No longer merely a floral headdress competition, the ball has evolved into an evening of Las Vegas type entertainment with a cast of over 100 people. The event featured headdresses of every description, dancers, showgirls and boys, cocktails, dinner, dancing, and a live auction. In addition, 150 volunteers worked to make the evening a success. Each year, the event is open to 1000 guests, and it has raised over $3,000,000 for
The Hope and Help Center.

For the past 3 years, Lightship Entertainment has donated specialty video montages and motion graphic sequences to make this fundraiser spectacular!