The city of Homs, formerly known as Emesa, strategically located in the central region of Syria, has been long linked to a folk belief that portrays its inhabitants as mad and fool. Historical and traditional sources also link the alleged madness and foolishness of the Homsians to the day of Wednesday, the so-called “Day of the Fool” or “Homsians’ Feast”, which is considered a special day. The legend regarding the “Day of the Fool” and its celebration during Wednesdays has been passed down orally in the local culture and its origins likely trace back to ancient times when the city was still called Emesa. Therefore, this article attempts at reconstructing history and origins about this folk belief, and exploring the reasons behind the supposed madness and foolishness of the inhabitants of Homs and their connections to Wednesdays by comparing three studies published after 2000s in Arabic by Homsian intellectuals, namely Al-Aḥmad, Samʽān, and Kadr.