So far as our local holidays go, I keep two quotes from On Piety in mind:
Quote"...Epíkouros loyally observed all the forms of worship and enjoined upon his friends to observe them..."
"...he is found to have taken part in all the traditional festivals..."
If the Hegemon wore sneakers instead sandals, I imagine he'd carve pumpkins, too.
But also,
Quote"...Anthḗsteria too must be celebrated..."
The first day of Anthestḗria shared a bit in common with the theme of Halloween (and other "Day of the Dead" holidays, globally). I mention it in the second part in my essay about holy shit:
Quote..."beginning with [DAY 1] Πιθοίγια (Pithoígia) the “Casket-Opening” during which “libations were offered from the newly-opened jars to the god of wine” and “all the household, including servants or slaves [joined] in the festivity of the occasion” — so long as that person was “over three years of age…” (Encyclopædia Britannica 103). Pithoígia resembles in many ways the Celtic tradition of Samhain, as well as its Christian analogue, All Hallow’s Eve save that Pithoígia is set amidst the floral scenery of Anthestēriṓn (mid-February-to-March), just in time for the wine to have reached its intended perfection as the flowers of next year’s harvest begin to bloom. Participants, within fragrant “rooms […] adorned with spring flowers” would, expectantly, open their tall πίθοι (píthoi, “jars of wine”) anticipating the prize within — symbolically, the jars represent the “grave-jars” of the deceased: fumes from the the previous season’s vintage escape like the vapors of the departed, liberated from their dark tombs. The souls of the dead are mythologized to have escaped the underworld to torment the living. “To protect themselves from the spirits of the dead,” as was the Attic tradition, Athenians were seen “chewing ‘ramnon’, leaves of Hawthorn, or white thorn, and were anointing themselves and their doors with tar” (Psilopoulos, Goddess Mystery Cults and the Miracle… 268).
I think Halloween is a fair analogy to the ancient Greeks days of the dead.
Overall, it's still really popular, if economic activity is any indicator. I think it's tough to get Americans to agree on anything, so if half the neighborhood will put out cobwebs and pumpkins, I think it's a victory for community spirit, but only insofar as the pleasure of celebrating a holiday.
Unless it produces no pleasure. In which case, individuals should practice avoidance.