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Wikipedia has various contests from time to time -- for good writing, site and logo designs, or great images or media -- to encourage and recognize brilliant, unusual, or specially-targeted contributions.
Contests have also been run on various other Wikimedia projects, generally eliciting excitement and support; the Wikinews writing contest in March/April and the second German writing contest (part of the International writing contest) both attracted over 10 unusual prizes from the community to hand out to the lucky/skillful winners.
You can also add to Ideas for new contests if you have a good idea for a contest and you can use this Toolkit model to reduce the time it takes to set up your contest.