The Annual Chili Cook-Off is an event in Springfield that, as implied by the name, occurs yearly. As indicated by the name, it serves as a place where various members of Springfield cook their own chili and feed it to visitors (including vegetarian chili). It also has a square dance session and, at least one time, a cotton candy machine.
Homer and Marge went to one of the Annual Chili Cook-Offs every year. Homer was also well known for being a taste-tester of various chili and being utterly merciless in his critique of them. However, during each visit, Homer ended up becoming "as drunk as a poet on pay day" and as a result doing something very humiliating. This eventually came to a head the year prior to the events of "El Viaje Misterioso de Nuestro Jomer" where Homer ended up becoming drunk, and then proceeded to strip naked and then bathe in a cotton candy vat, while declaring that everyone look at him as he was "a puffy pink cloud", to everyone's shock, as well as his running off giddily with the kids being frightened by his antics, and eventually collapsing to the ground as two dogs proceed to lick off his cotton candy "clothes", much to Marge's embarrassment. This event in particular acted as the last straw for her, and resulted in her going for drastic measures to ensure Homer couldn't go to the cook-off, including trying to prevent any evidence of it occurring (by cutting out the newspaper mentioning the cookoff, using a vacuum cleaner to drown out Lenny Leonard's attempt at calling Homer to notify him of the event, and even taking up smoking). Homer eventually managed to find out when stepping out to get fresh air, with Marge eventually caving and allowing themselves to go to the cook-off, although only under the condition that Homer remain sober for the entire event. Homer ultimately managed to keep his promise, although he came very close to breaking it after ingesting a Guatemalan Insanity Pepper-laced chili by then-Chief Clancy Wiggum. This event also lead to a near breaking of his relationship with Marge when Homer proceeded to flee the Cook-Off in an apparent psychotic break (ironically, despite Marge's assumptions, his psychotic break had absolutely nothing to do with his drinking beer, but was the side effect of a second try of the Guatemalan Insanity Pepper).
- A Little Bit of Lenny (Doesn't actually sell chili, but sells ingredients and equipment for making it; Helmed by Lenny Leonard);
- Muntz Family Chili: It takes weeks to make Muntz (Helmed by Nelson Muntz);
- Old Elihu's Yale Style Saltpeter Chili (Helmed by Charles Montgomery Burns);
- Professor Frink's Virtual Chili (Helmed by Jonathan Frink)
- Firehouse Ned's Five Alarm Chili (Helmed by Ned Flanders and his family; though it's revealed to only be two alarm, two and a half alarm tops);
- Moe's Chili Bar (Helmed by Moe Szyslak);
- Chief Clancy Wiggum's tent (In the events of "El Viaje Misterioso de Nuestro Jomer", Wiggum, in large part due to Homer's merciless reviews, proceeded to add to his chili an extra ingredient specifically for Homer, the Guatemalan Insanity Pepper.);
- Beer Garden: Proof of Age or Exact Change Required (Not actually selling chili, but sold beer);
- Joe's Spoons: Hand Waxed (not actually a chili stand, but sells spoons for eating chili);