The parade made its debut on September 24, 2007. It returned on September 25, 2008 as part of the Disney's Haunted Halloween event with a new finale of the ghost pirate ship float. The Headless Horseman was featured in the prequel of the parade in the 2011 Halloween event as Headless Horseman's Procession. Since then, the parade has been running in each Halloween event until late 2013.
The Princess Float from the park's former parade Disney on Parade was used by Maleficent (2007-2009, 2011-2012) the Witch (2012 only), and some of the Disney Villains (2010), and ran from 2007 until 2012.