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The Wintersday 2005 Update added a lot of content celebrating the holidays in Tyrian style. The celebration is centered around Wintersday, the Tyrian equivalent of New Year's and groundhog day. On this day a struggle between Dwayna and Grenth takes place to determine whether the day will be filled with joy and gift-exchange, or gloom and somber remembrance. According to legend, if Dwayna won, spring would come early, and if Grenth won, winter would last longer than usual.

The update introduced the following new features:

  1. The three major cities: Ascalon City, Lion's Arch and Droknar's Forge were decorated for Wintersday, along with the The Tombs.
  2. Wintersday 2005 items that were offered by Wintersday 2005 collectors located in these cities.
  3. Wintersday 2005 quests were offered by Old Nickoles in Lion's Arch.
  4. Candy weapons were offered by Candysmiths in the three major cities and the Dwayna vs Grenth snowball arena. These required Candy Cane Shards which dropped from slain monsters.
  5. Presents appearing all around the three cities. Players can pick them up and give them to children NPCs in the cities before the Grentches get them.
  6. A Snowball Fight Arena where teams fought with new snowball fighting skills to see who can collect presents for their side the fastest.
  7. The Enchanted Snowman... A set of four snowmen were available as henchmen in Lion's Arch, Droknar's Forge, and Ascalon.

On Wintersday (Dec 31), there was a competition between Dwayna and Grenth in Lion's Arch. An Avatar of Dwayna and an Avatar of Grenth appeared in each district; Dwayna's next to the Wintersday Tree and Grenth's near the Carolers of Grenth. Supporters of each would gather around the aforementioned avatars, and after a long speech and showering of gifts, they would be tallied. If Dwayna won, Yule Caps would be given to everyone present, the district would be lit with fireworks and gifts would appear around her for 15 minutes. If Grenth won, all those present would be given Horns of Grenth, fireworks would also begin, and murderous Grentches would run around, spawning some lethal presents as well as some legitimate gifts. Additionally, his supporters would be killed and bone horrors summoned from their cadavers. Only those who were present at the original tally would receive horns or a cap. These competitions took place at 12pm, 3pm, 6pm, 9pm, and 12am(PST in US, GMT in Europe). The international districts took place at 1pm, 4pm, 7pm, 10pm, 1am, 5am and 8am GMT.

To ensure people received the gifts that they wanted, players tried to designate the various districts as either 'Grenth supporting' or 'Dwayna supporting', the results varied, but this seemed to work for the most part.

Wintersday Event ended on January 6 at 8pm GMT.