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"I don't know that there are any true stories behind the Jester's Festival. Some say it happens because Sheogorath turned the whole world mad! Others say it sprung from Mer wanting to know what it's like to live like Men. Who really knows?"
The 28th of Rain's Hand is Jester's Day in the cities of Tamriel. On this day pranks are set up from one end of the cities to the other. It is as if a spell has been cast over the community, for even the most taciturn and dignified councilman might attempt to play a joke. This event makes an appearance in The Elder Scrolls Online as the Jester's Festival in celebration of April Fool's Day, and can be seen as such. The Festival has Heralds that see to it that the holiday goes on normally. The origin of this holiday can be contested and is not yet known, however, there are rumors, such as Sheogorath turning the whole of Nirn's mortals mad, or the first of Mer wanting to research the Men's lifestyle, such as humor.
The Thieves Guild attracts particular attention, because everyone looks for pickpockets in particular. [source?]