While I grew up in an Orthodox Jewish community in Brooklyn, Halloween was largely taboo. I believe I can safely say that literally nobody in my social circle celebrated the holiday—unless you count an egg being thrown at your school bus during the ride home on Oct. 31.
Why do some Jews abstain from Halloween? Some cite the pagan roots of the holiday, others the fact that Jews already get to wear costumes on Purim, and others that it's simply "goyish." The counter-argument would be that Halloween isn't "goyish," but American—just like Thanksgiving.
I'm no longer living in the Brooklyn shtetl, yet to this day I've never celebrated Halloween. I don't really feel "left out," and something inside of me feels proud about clinging onto this facet of my experience with Jewish tradition. But is it really tradition at work here, or self-righteousness? The popular Jewish educational websites Chabad.org, Aish.com, and MyJewishLearning.com offer analyses on the Halloween debate here, here, and here.
With Halloween falling on a Friday night this year, an additional question beyond "Is Halloween goyish?" arises: Is celebrating Halloween "Shabbasdic?" If you, like me, are an observant Jew struggling with the annual Halloween dilemma, hopefully this Oct. 31 will bring you some clarity on the issue.