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Judaism was an early monotheistic religion, and stood in contrast to the dominant paganism of the day. Therefore it said to stay away from anything that even smelled somewhat pagan. And Halloween has pagan roots. That's all.


The Rabbi of my shul spoke about this question this year. He said that in Israel, a person from chutz la'aretz should sit in a sukkah lechatchila on Shmini Atzeret.

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