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There's supposed to be two parts to it from what I've heard. You can either go into houses wearing masks to get lollipops to give to Jack so you can get Creepy furniture. Or you play mini games with your villagers for parts of the spooky series, and if you lose, they'll turn your clothes into the patched clothing (shirt, pants, dress, hat, shoes) or any of the pumpkin headgear.
Apparently you're meant to talk to your villagers before Halloween to find out what they like and what they're scared of, but every time I talk to my villagers they don't say anything to me and just ask me for favours so I have no idea.
Here is something I found on Tumblr, hope it helps
Halloween is a fantastic event that is quite active. Think of the things you have to do as a cross between the harvest festival (running to houses) and christmas (learning about the villagers).
October 1-7
During this week, the Pumpkin king will stop by your town and talk to you. You may or may not have to find him. He will tell you to purchase as much Halloween masks from Able’s and as much candy as you can hold at Nook’s. He’ll tell you that you need to use the masks to scare villagers on halloween and candy will be used as prizes for the villagers.
October 1-30
During this month, talk to your villagers. You will learn about what they like and what they are scared of. There are 6 masks and they are scared of most of them, tough against others, and extremely scared of one. You want to find out which they are extremely scared of.
October 31 (6pm-12am)
Most of your villagers will be in their houses. These are the ones you need to scare. The others will be wandering around your town looking for you. They will get you and they will trick you. They are all dressed as the Pumpkin King. Why? Because the Pumpkin King is also wandering around.
Your jobs:
- Halt the impostors
- Scare the indoor villagers
- Find the real Pumpkin King (difficult since the impostors and him reset when you enter/exit a building)
- Get lollipops
Lollipops?
Yes, lollipops. You can’t buy these. You can get them from scaring the indoor villagers. You give these to the real Pumpkin King and he’ll give you a piece of the Horror set. The Horror set is unorderable, the pumpkin/halloween set is orderable and you can buy it at nook’s during October.
The Pumpkin King loves lollipops and is more than happy to part with his Horror set for one.
He also likes candy but will only trade Halloween furniture, masks, or extra clothing. Rarely though, he will trade a horror piece for candy. It’s very rare and it’s a waste to keep trying candy for it.
You can get candy for failing to scare the villagers. They will play a game with you when you fail and will give you a candy if you win. If you choose the mask they are tough against, or you lose their game, they will do a trick on you. Tricks depend on the villagers.
The fake Kings outside will try to catch you and will play a game with you or just do a trick. Same rules — you win, candy; not, trick
Since I am a Time Traveler, I just had my Halloween awhile ago.
All but two of my villagers were outside (so that was a bit boring and I could only get two lollipops!)
But the plus side to having your villagers wandering around is that if you aren't wearing a mask already then you can get some free pumpkin masks! I collected all of them since they're adorable >w<
To get the patched clothing, old wall and floor, and the jack-in-the-box, would you say to leave everything at home and just have junk and random items in your invo as well as random clothes and purposely lose the minigames?