What's your take on whether or not Jewish kids should participate in Halloween?
How to Do Halloween
I am a big proponent of Halloween. That is, I'm a big proponent of kids dressing up, getting to know their neighbors and possibly eating too much candy. But don't quote me on that last part to my 2-year-old! Halloween was one of my favorite childhood experiences. My two best friends and I would dream up group costumes for months leading up to the holiday. Our greatest achievement was probably the year we dressed up as R.E.M. We would dress up at school, we would dress up at home, we would dress up for our town's annual parade. After our big night of trick-or-treating, we would come back to my house, drink hot chocolate, and meticulously arrange and trade our treats. One neighbor always gave homemade popcorn in ziploc bags, which we ate first (ah, small town life), and my dad "confiscated" all the Baby Ruth bars. This is the stuff of childhood memories!
I am not a big proponent of scary costumes, gorey anything or vandalism. I find the "excuse to dress slutty" trope tiresome. I don't think 20-somethings actually need Halloween as another excuse to get drunk. I'm afraid my 2-year-old will eat too much candy or that her costume will break or that she'll decide she needs a new costume 10 minutes before leaving for preschool in the morning. I really, really didn't like the fake blood a neighbor had on his window last year that stayed up past Thanksgiving. Clearly, some of my personal preferences are at odds with how Halloween is carried out in the real world — though being anti-vandalism isn't so much a personal preference as a civic duty — but none of this has anything to do with Judaism.
Halloween is akin to Thanksgiving in my worldview: secular, celebratory, fun. It's also a rare opportunity for Jews to be part of a celebration that mainstream America knows about. When I was growing up in my small town with an even smaller Jewish community, Halloween was one of the few times that I was excited about a holiday that everyone else was excited about. It felt great to have that kind of insider experience. Despite its origins in both Christian and pagan traditions, Halloween as it's currently celebrated in mainstream America is not a religious holiday.
If you decide that, as a Jew, Halloween is outside your celebratory purview, that's fine, too. There is good precedence for that opinion, and using the "Purim's in another few months" line is totally reasonable. If I didn't have such fond Halloween memories of my own, I might even take a different stance. Then again, our neighors have started a tradition to have a kids' Halloween block party, and I cringe at the idea of separating our kids from this neighborhood event. Thanksgiving is a family holiday; Halloween is a neighborhood holiday. Regardless of what approach you take, just remember that post-Halloween sales are the best time to buy Purim costumes.