It’s funny how chance encounters—OK, eavesdropping—can give rise to research. There I was, in the bathroom of a Jewish cultural institution, when I overheard two women animatedly discussing from the comfort of their respective stalls what they had in mind to wear for Halloween. Though Yom Kippur was just around the bend, it wasn’t that holiday, or, for that matter, Sukkot, the Jewish harvest festival soon to follow, that energized and delighted them so much as the prospect of the “amazing costumes” they would don for its Celtic counterpart, then a few weeks away.I lingered awhile in the bathroom, my curiosity about the identity of these two women having gotten the better of me. Lo and behold, when they emerged from behind the doors of their respective stalls, they turned out to be two of my very own students, both of whom were enrolled in a graduate program designed to promote Jewish culture and the arts. So much for that, I thought to myself. Smiling wanly, I acknowledged my students’ presence and then beat a hasty retreat—from them as well as their perfervid embrace of Halloween.This episode, though, stayed with me, prompting me to take a more sustained look at the relationship between contemporary American Jews like my students and Halloween’s hold on the popular imagination, which has grown by leaps and bounds over the past 20 years. So pronounced is Halloween’s presence on the street and in the marketplace that some contemporary observers have characterized it as more of a seasonal phenomenon than a one-day affair.Have American Jews followed suit and, like their neighbors, taken to Halloween with increasing relish? Has trick-or-treating become an accepted ritual within modern-day American Jewish households? Or is it a bone of contention and, like Christmas, more of a “dilemma” than “harmless fun?” And what of the past? Did earlier generations of American Jewish children don costumes and gobble too many sweets?***When it comes to marking Halloween, fragmentation rather than consensus rules the contemporary American Jewish roost. For every American Jew who can’t wait for Oct. 31, there are those who wish it away, turn a blind eye, shrug their shoulders, or sigh. Some rabbis and educators across the board frown on the practice of trick-or-treating; others avidly welcome it while still others prefer to temporize: What you do at home, they say, is your own business.Much the same can be said of the grassroots. Some American Jews, likening Halloween celebrations to a goyishe zakh, a non-Jewish practice that Jews would do very well to avoid, urge would-be celebrants to stay far, far away—or, better yet, to make the most of Purim, which also affords the opportunity to be someone else and to eat lots of candy. Others insist that Halloween is good, clean fun as well as an exercise in neighborliness, so what could be wrong with that? Still others maintain that Halloween, seemingly free of the domestic tension that attends Christmas or Passover, is a boon to interfaith families. “I think that’s why everyone enjoys this,” explains a Jewish woman whose spouse is Catholic.In contrast to American Jews today, for whom online discussion about the dos and don’ts of Halloween is as full and varied as a trick-or-treater’s collection of loot, earlier generations did not make much of the autumnal holiday. A cursory examination of Jewish children’s books in pre- and immediate post-war America, for instance, came up empty. Consider the popular figure of K’tonton. Known as the “Jewish Tom Thumb,” this mischievous imp of a character was forever getting into and out of all sorts of scrapes. K’tonton swung on a lulav, rode a runaway dreidel, and stowed away in a synagogue. What K’tonton didn’t do, though, was trick-or-treat.Jewish parenting literature, a growth industry in postwar America, as the research of historian Joshua Furman vividly demonstrates, didn’t have much to say about Halloween, either. Its concern focused almost entirely on meeting the challenges of Christmas and, conversely, with how to render Purim, Passover, and Hanukkah appealing to American-born Jewish kids. Halloween didn’t even merit a how-de-do.It’s not that Oct. 31 was no big deal back in the day. Although costumes tended to be homemade rather than store-bought and candy options far more limited than they are nowadays, newspaper accounts as well as articles in women’s magazines suggest that it was a lively and well-received occasion, all the more once UNICEF—and child psychology—entered the picture. “Halloween,” observed The New York Times in 1960, “provides a healthy escape from year-round repressions and is especially valuable to children whose lives are excessively ordered and controlled.”A welcome, if temporary, release from parental strictures, the Halloween of yesteryear was not seen by American Jews as a threat, the stuff of cultural anxiety. Rather, it was understood as just one of those things that suburban American kids did, regardless of their ethnic and religious background: an innocent pastime, a totem of childhood. Besides, many Jewish parents in postwar America often adopted a “live and let live” attitude toward those elements of American popular culture such as Halloween that seemed to be benign, or, at the very least, not worth fighting about.What changed in the interim? A number of things, from the increasingly outré nature of Halloween to the Jewish community’s tilt to the right. Once associated almost entirely with kids, Halloween became the darling of the adult gay community, whose annual parade in Greenwich Village, a product of the early 1970s, gave new meaning to shape-shifting and boundary-crossing. Reveling in its disdain for respectability, this urban festival, writes anthropologist Jack Kugelmass, “celebrates the irreverent and the lascivious.” Halloween’s popularity within the gay community, he speculates, might even be seen as an “implicit rejection of a collective self-prescribed within the Judeo-Christian tradition,” a self without encumbrances. Halloween had lost its innocence.Concomitantly, American Jewry’s changing landscape also had a great deal to do with the community’s shift in perspective toward Halloween. The growing prominence and newfound assertiveness of Orthodoxy and with it, the hardening of cultural boundaries, rendered the holiday more and more suspect, out of bounds. Before long, even non-Orthodox communities began to grapple actively and publicly with Halloween’s shortcomings. As one concerned American Jewish woman told a reporter from the Detroit Jewish News in 1990, “it’s not our mission to respond to the gentile calendar.”That may be. Even so, come Oct. 31, thousands of American Jewish children, their parents in tow (or sitting in an idling car) will happily spread their wings and dash about in the cool of an autumn evening. What should we tell them? Boo?!***Like this article? Sign up for our Daily Digest to get Tablet Magazine’s new content in your inbox each morning.