Collecting Candy on Halloween
Though many Jewish children go trick-or-treating, this writer (among many others) believes the practice runs counter to Jewish law.
This statement appears to be a truthful recounting of the modern American celebration of Halloween. The vast majority of people who celebrate Halloween have absolutely no religious motives at all--it is an excuse to collect candy or engage in mischievous behavior.
However, it is worth noting that there are still some people who celebrate Halloween religiously, and there are occasional court cases about employees who seek to take religious leave on Halloween day as a religious holiday.
Thus, the question about Halloween is whether Jewish law allows one to celebrate an event that has pagan origins, where the pagan origins are still known and celebrated by a very few, but not by the vast majority of people who engage in this activity.
Halloween & Halakhah
In order to answer this question, a certain background into the nature of the prohibition to imitate Gentile customs must be understood. Tosafot [a medieval Talmud commentary] understands that two distinctly different types of customs are forbidden by the prohibition of imitating Gentile customs found in Leviticus 18:3. The first is idolatrous customs and the second is foolish customs found in the Gentile community, even if their origins are not idolatrous. Rabbenu Nissim (Ran) and Maharik disagree and rule that only customs that have a basis in idolatrous practices are prohibited. Apparently foolish--but secular--customs are permissible so long as they have a reasonable explanation (and are not immodest). Normative halakhah follows the ruling of the Ran and Maharik. As noted by Rama [Rabbi Moshe Isserles, c. 1525-1572]:
"Those practices done as a [Gentile] custom or law with no reason one suspects that it in an idolatrous practice or that there is a taint of idolatrous origins; however, those customs which are practiced for a reason, such as the physician who wears a special garment to identify him as a doctor, can be done; the same is true for any custom done out of honor or any other reason is permissible."
Rabbi Isserless is thus clearly prohibiting observing customs that have pagan origins, or even which might have pagan origins. His opinion, the most lenient found in normative halakhah, is the one we follow.
Of course, independent of the halakhic obligation to avoid Gentile religious customs, Jewish law forbids a Jew from actually celebrating idolatrous religious events himself.
Based on this, in order to justify candy collection on Halloween, one would have to accept the truthfulness of any of the following assertions:
1) Halloween celebrations have a secular origin.
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