Here's the bottom line: it's Shabbes, not Halloween.
You all know that I am very relaxed about most of the holidays that America and its retailers have adopted and secularized. While it will always be inappropriate for the synagogue or the Jewish community to celebrate Valentine's Day or St. Patrick's Day, and while our social observance of New Year's Eve flirts with the liturgical calendar of the Roman Catholic Church, most of us happily dress in the color scheme of the day and support the greeting card industry. And while both the origins of Halloween (very pagan) and the contemporary practice of trick-or-treat (extortion and indulgence) are contrary to Jewish values, few of us deny our children the chance to roam the neighborhood and join in the festivities. After all, who does it hurt?
This year, it could hurt.
All Saint's Day occurs on Saturday, November 1, with the usual night out being Halloween, Friday the 31st. And, just in case your calendar does not list it, Shabbat will occur those very same days that week. As a Jew, you have a decision to make which will communicate a message about the relative importance of Jewish values and Jewish identity in your life.
Don't underestimate the importance of this decision. Many times you and those in your family will come to an intersection in the road of life, and a choice of paths will be necessary. The short-term disappointment which may come with denying yourself or your family members a good time this once will teach two important lessons for the future. First, the self-indulgent choice is not always the right choice. And second, minor disappointment passes in a flash.
If you send your children out in costume Friday night or dress up yourself to go to a party, then the message you send is clear: this frivolous and indulgent set of customs is of greater importance than Shabbat. The right place for Jews this Halloween is in synagogue and at home.
And if you really want to observe something of Halloween in consonance with Shabbat, let me suggest a text for study that evening. The first Mishnah of the tractate Shabbat deals with what to do if a beggar shows up at your house on Shabbat asking for food...
See you in shul.