Winter Holiday is a time in Toontown between December 14 and January 4. Just like Halloween, there are special things happening at this time. The streets are decorated, winter parties, the special holiday Cattlelog items, and caroling for a snowman head.
- Main article: Winter parties
Winter Parties first introduced flappy and inflatable cogs. Also in the catching game for parties, the fruit changes to presents.
Special holiday cattlelog
Just like during other holidays, Clarabelle's Cattlelog has special items pertaining to Winter Holiday. There are clothing, furniture, and statues for your garden. Once Winter Holiday is over, toons can still use these items, but they cannot be bought until next Winter Holiday, unless it goes to the backorder.
- Main article: Snowman head
Caroling is an activity toons can do during this time to get a snowman head. In order to obtain a snowman head, visit all of the following buildings, in any order:
In each building, when a toon says one of the caroling SpeedChat phrases, they will receive 100 jellybeans. In the sixth building, the toon's head will turn into a snowman head.
- Regardless if a caroling building is taken over by cogs or not, using the phrase inside the building will still give out the jellybeans.