I noticed that one user has a cool pirate hat. However, there is no description of what's required to get a hat like that on the winter bash page. Are there "secret" hats, or is this one given out on other SE sites?
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If you click on the user's avatar on their profile page, you can see their hat collection. If you hover over the pirate hat, a little description offers a hint:
If you know the name of the hat and want a more detailed description, you can go to http://winterba.sh and add the name in the URL, hyphenated and in lowercase.
For the pirate hat you're asking about: http://winterba.sh/shiver-me-timbers
Of course, this won't work if you don't know the hat's name. :)