Halloween

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"Happy Halloween!" from the whole gang.

Halloween is an important holiday for the characters in the Homestar Runner universe. Since 2000, the first year of the website's run, The Brothers Chaps have liked to make an annual big Halloween toon every year up to and including 2009, after which Homestar Runner went on hiatus, before again making them since 2014. Since 2003, Strong Bad has hosted a slide show of Fan Costumes shortly after Halloween every year of the aforementioned active period (except 2004), as well as since 2015.

Traditions

Every major Halloween toon has the main characters dress up in different Halloween costumes. These costumes usually relate to '70s, '80s and '90s pop culture. These costumes are often rather obscure in nature, and a running joke involves the characters' difficulty identifying each other's costumes, not that this prevents Homestar from being confident in his own guesses.
Unlike most other toons on the website, the Halloween toons feature every main character. Each year, Homsar appears in an Easter egg after clicking on something relating to The Poopsmith, save for Homestarloween Party, in which he did not appear at all (only because he had not yet been created) and Which Ween Costumes?. In The House That Gave Sucky Tricks and Later That Night..., he appears automatically without having to trigger an Easter egg.
Starting with The House That Gave Sucky Treats, after the toon is over, the characters will all group together and discuss one another's Halloween costumes. Since Pumpkin Carve-nival, clicking on selected characters while grouped together will start a short conversation with them and other characters, usually on the topic of the selected character's costume.
A running gag throughout many Halloween toons is for Homestar Runner, or on rare occasions someone else, to mention Witch's Brew. This started in Pumpkin Carve-nival when Homestar (actually Strong Bad dressed as Homestar) mentioned Witch's Brew in odd context throughout the toon.
The Goblin is a recurring character in a large number of Halloween toons. He was created in Homestarloween Party, when Homestar imagined him while telling a Halloween story. The Goblin has since come to life and has made cameo appearances at different times, sometimes seeming to (or actually) appear out of nowhere.
The Spooky Woods appears as a setting for almost every Halloween toon (though not necessarily the only setting). The Halloween House and The Graveyard appear to be located in these woods. The woods also appear to be a favored location for various Halloween-themed activities such as pumpkin judging contests and trick-or-treating.
Since 2007, there has been a teaser before the Halloween toon is released. They always include the characters, silhouetted in their costumes, with a message, usually saying when the toon will be released.