Halloweenland began life back in 1997, when it was the only area of the resort to celebrate Halloween. A few decorations were added around Frontierland, with a much darker style of Halloween to the one that is celebrated today. Back then in Halloweenland you would be sure to bump into one or two zombies, a mummy, maybe even a grim reaper. The scarecrow performed trick or Treating, and live acts would perform on the Spider web stage in the centre of Frontierland, directly opposite Big Thunder Mountain as you enter the land. The Mark Twain was even given a seasonal makeover as the Mummy and later to be named Phantom Cruise Line, decked out in white cloth on the decks. This scary vessel was pulled by a giant Phantom statue and would tour around the Rivers of the Far West.
In the year 2002 the Halloween celebrations were controversially moved from Frontierland to Fantasyland, giving Fantasyland a very odd feel. Merlin however performed a Halloween themed version of his famous “Sword in the Stone” show. By 2003 the celebrations returned to their true home in the Wild West in Frontierland. Bringing with it extra decorations, and a very strange look to the Ravenswood Manor at the highest point of Thunder Mesa. Phantom Manor was covered in brown and autumnal coloured tarp, with pumpkins placed around the Manor's surroundings.
However the biggest shake up since 1997 was just around the corner, 2004 brought with it that orange invasion from Spooky Street (Main Street USA) the Pumpkinmen. With the invasion of the pumpkinmen into Frontierland their statues took residence all around, and with them came a storyline, this was the first time a storyline was explained. The Pumpkinmen also placed a huge crane in the land and it reached over to Big Thunder Mountain, the story explained this was how they gained their pumpkin orange paint, they ever so much loved to haunt Main Street and now Frontierland with. The Spider web stage would remain for one final year opposite Big Thunder Mountain, however the scarier acts such as the Graveyard diggers would share time with much more family friendly haunts, the Pumpkinlady Clog Dancers, among other variations of the Pumpkin people universe. On the final days of October Phantom Manor gained what to most would seem a bed sheet overlay. To the dismay of many who loved the exterior of the manor, the tarp was laid over the whole exterior. This would turn out to be for the benefit of a special show during the two Halloween Soiree evenings, the story of Phantom Manor would be digitally and rather artistically projected directly onto the Manor during these events.
The mischievous Pink Witches were given a home in 2005 for what was to be part of the ongoing story of Halloween between Pumpkinmen and the witches. The statues placed, were slightly of a lesser quality than those the pumpkinmen had been given in 2003 and 2004. As the Pink Witches arrived they brought with them a European steriotype for each country around Europe. A tea drinking witch for Britain, or perhaps a fries eating witch for Belgium, this type of prop was a very strange choice for Halloween. It was recieved with mix feelings, though for now it is there to stay. However as the witches took over half of the land, a battle was being fought on the balconies of Restaurant Fuente del Oro, the bankrobbers were fighting it out. This show was a show once seen many years before in Frontierland, but disappeared just like many others, sadly it was only to last for one Halloween Season.
Spiderweb stage was even moved to the back of Halloweenland, next to the Cowboy Cookout, painted pink and called the Pink Witch stage, for one final year some of the scarier acts performed. By 2006 the whole season stayed very similar in Halloweenland, though the acts changed to more Disney classic and with it a touch of Stitch arriving to take over Halloween.
