PrideFest was fortunate again in 1999 to have August dates. This time it was due to the five weekends that fell during the month of July. African World Festival, one of the other festivals that used the grounds, opted to take late July dates rather than their traditional first weekend in August, giving PrideFest the opportunity to have another late summer celebration. Despite thunderstorms in surrounding counties, only a few showers fell on the festival on Saturday, with the weather clearing again in time for the Sunday parade. 13,455 attendees passed through the gates and enjoyed three days of camaraderie. The headliner for the festival was Kathy Sledge and her "We Are Family" echoed in the community for many months thereafter.

The Board of Directors for 1999 Pride was (in the order they were listed in Pride records):

• Jane Baudeliare
• Ted Berg
• Jill Clark
• Susan Cook
• Rick Finger
• Jennifer Johnson
• Chris Klein
• Suzanne Krueger
• Michael Lisowski
• John Prentice
• Russ Reiter
• Dawn Schaeffer
• Sheldon Schur
• Del Slowik
• Jerry Spillner