Anime doesn't usually have Halloween or Christmas specials. I especially
don't think Naruto will have a Christmas or Halloween special, but if you really wish for it to have some, send a fan letter to its creator, Masashi
Kishimoto San, and maybe he might consider to make both if you're lucky.
Anime comes from Japan, and they don't have the same holidays as us, as new years is their best holiday instead of Christmas or Halloween. Besides, some of the characters already look frightful enough, like gaara with his eye makeup and kankuro with whatever gunk is on his grill.
Come to think of it, Orochimaru would make a good Dracula, and chouji would make a good pumpkin with his expansion jutsu and a lil orange paint!