Wintersday is an annual special event which celebrates the Tyrian New Year according to the Mouvelian calendar and Dynastic Reckoning. It is the celebration of the end of the Season of the Colossus and the beginning of the Season of the Zephyr. During Wintersday, snow covers the lands and the Snowmen and Grentches appear to spread their versions of the celebration across the land, through giving and destroying presents respectively.
- Primary article: Wintersday: The Wondrous Workshop of Toymaker Tixx
During Wintersday 2012, Toymaker Tixx visited the cities of Tyria to introduce his new toy inventions in The Wondrous Workshop of Toymaker Tixx release. These toys weren't always fun and games as the sneaky Skritt want to steal the toys for themselves and malfunctioning toys and machines are about.
- Primary article: Wintersday 2013
In the first A Very Merry Wintersday release, Toymaker Tixx visited Lion's Arch once again during Wintersday 2013 and gave access to his variety of activities. Ho-Ho-Tron and the bard Marcello DiGiacomo could be found in the city raising funds for repairs to Divinity's Reach which was attacked prior by Scarlet Briar.
- Primary article: Wintersday 2014
Wintersday 2014 started on December 16. Wintersday events were held at Divinity's Reach, since the rebuilding of the decimated Lion's Arch is still ongoing, and as one Wintersday reveler said, humans "appreciate" it more than the other races do. The player character received a mail from orphans of Divinity's Reach, asking for help in dealing with a grawl named Grawnk, who stole Wintersday ornaments. A replica of Ho-Ho-Tron was installed to accept donations.
- Primary article: Wintersday 2015
- Primary article: Wintersday 2016
Wintersday 2016 started on December 13 and ended on January 10, 2017. Wintersday events are being held at Divinity's Reach.
- Primary article: Wintersday 2017
Wintersday 2017 started on December 12 and ends on January 2, 2018. Wintersday events are being held at Divinity's Reach.