The event has been running nearly every year since 1990, when Pensacola businessman Bill Dollarhide funded much of the expense out of his own pocket so up-and-coming local acts could reach a wider audience. In turn, part of the revenues were given to the Alzheimer's Foundation, to which Dollarhide donated regularly.
In the years since, Dollarhide decided to incorporate bigger names to bring more crowds. Popular national and international acts, such as Chingy, BBMak, Willie Nelson, O-Town, The B-52s, John Michael Montgomery, Creed, Collective Soul, Three Doors Down, Doobie Brothers, Bruce Hornsby, Lonestar, Smashmouth, Patti Labelle, Little Feat, Hank Williams Jr., Train, Hootie and the Blowfish, Live, Blues Traveler, Papa Roach, Sugar Ray, Lit, Morris Day and the Time, Run DMC, Eddie Money, Neville Brothers, Allman Brothers and Everclear have played for fans at SpringFest.
The novelty of SpringFest is its setting right in the heart of downtown. For all three days, multiple blocks are cordoned off to cars, and large stages are set up on street corners. Multiple acts play at any given time throughout the day, with the best-known acts saved for evening performances. The anticipation for SpringFest is large in the community, with the Pensacola News Journal dedicating an entire issue of their Weekender lifestyles magazine to the event.
Although the event has more or less stayed true to its roots, the sponsors of Florida SpringFest have incorporated new ideas and locales, which were not successful. In 2004, SpringFest was held inside the Pensacola Civic Center as opposed to the normal outside setting. The number of bands playing at the same time in an enclosed area proved to be hard for listeners to decipher, and the experiment was regarded as a failure. In 2005, SpringFest returned to the streets of downtown. However, the sponsors could not recoup their losses from 2004 and make new profits for that year, and canceled the scheduled SpringFest for 2006. The 2007 SpringFest was also cancelled for many of the same reasons, including sponsorship issues.
SpringFest recently announced it will not return in 2008, but will try again in 2009. Sponsors include such international firms as Coca-Cola, Miller Lite, Budget Rent-a-Car, Siemens, and Hilton Hotels as well as private individuals. Local radio stations, as well as the Pensacola News Journal and WEAR-TV, are secondary sponsors. Dollarhide has not sponsored the event in recent years. The festival costs approximately $1,000,000 to produce.