The year 2003 brought further expansion of the grounds with a new stage area to feature 80's legend Pat Benatar. Additional advertising was arranged in the Chicago and Minneapolis markets, and the festival was poised to rise to a new level. Unfortunately, expectations for increased attendance did not materialize (partly because of inclement weather), and the festival sustained a debt of nearly $150,000. The festival was in dire straits.

In the fall of 2003, a diverse group of community members pulled together an advisory group to chart the festival's options. Led by the Cream City Foundation (CCF), the PrideFest Task Force was formed to forge ahead with a plan to reduce the debt and produce a festival for 2004. The community had come too far to let the festival end so tragically. Drastic steps were taken, including a major shakeup of the Board of Directors, and shutting down the 12-month-a-year permanent office that PrideFest had rented out.

An appeal for help was made, and through amazing generosity, a group of people affectionately called the PrideFest Legacy Angels donated nearly $60,000 to pay down some of the debt. Their devotion to the mission of PrideFest helped create a belief that the festival could rise again.

The Board of Directors for PrideFest 2003 was (in the order they were listed in Pride records):

• Ted Berg
• Bo Dyer
• Michael Goertz
• Sherri Goldberg
• Nick Laurent
• Lil Lau
• Michael Lisowski
• Pete Minns
• John Prentice
• Paul Sherry
• Marcus Smith
• Cindy Taylor