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Out With It
As you collect candy, there becomes an obvious and inevitable activity to be done with it all. That is to say, as any good 6 year old will tell you, stuff as much as possible in your happy little face, all at once, until you become absolutely sick to your stomach.
The six year old was right, and this achievement proves it. Once you've successfully gathered enough candy, eat it all at once. When your character pukes up all that sugary goodness due to an Upset Tummy, the Out With It achievement is granted.
Bring Me The Head of ... Oh Wait.
This is probably my favorite achievement title of all time. To obtain Bring Me The Head of... Oh Wait, you need to go to the Scarlet Monastery and enter the Graveyard. About halfway through, you'll see a small altar and pumpkin. Interact with the objects there in order to summon the Headless Horseman. The Headless Horseman will appear. Kill him to receive the achievement.
The Headless Horseman fight isn't the most difficult thing ever, although we can't guarantee his loot table has been updated yet. He's basically a tank and spank. Every so often, his head will fly off his body. Kill the head. Then, when the head and body rejoin, kill the body. Repeat until he's dead. The head can be a little difficult to target, though, which probably is the most difficult part of the fight.
Edit: We now know his loot table - you can find information about it in this post.
The Savior of Hallow's End
Every hour, the Headless Horseman will attack one of your faction's starting zones. You get quests from the Orphan Matrons, who beg you to stop him. In order to complete the quest, your goal is to put out the fires -- not to actually kill the Horseman. You'll have an easier time of it if your faction mates lend a hand, so it's best to get this achievement done early, when everyone else is also trying to get it done.
That Sparking Smile
If you dutifully trick or treat every hour, you will eventually be granted a toothpick. In order to get this achievement, use the toothpick. Voila, finished.
Rotten Hallow
Rotten Hallow is a little more difficult, but not amazingly so. It's a little different depending on whether you're Horde or Alliance. You've got to go to the Hillsbrad Foothills, and complete either the Horde or Alliance seasonal quests there. It all revolves around stink bombs (or fresh pine air fresheners), and whether or not the Horde get to burn a wicker man.
