Halloween

[note: I think I misread your original comment, but thought my comment was still worth posting. I originally thought you said "it seems like your solution also has nothing to do with Halloween'". The short answer to the one you actually said was "but I miss Halloween, tho." This comment is for people who actively want Halloween in their lives, not who are clinging to it out of misguided sense of obligation, which I agree some people do and which is silly]

Those are also valid suggestions, and I definitely sympathize with people who don't consider my original suggestion valid (whether because their concerns were more shaped like my-current-understanding-of-Katja's than mine, or some other reason)

I don't really think there's such a thing as the definitive True Spirit of Halloween, since it's been evolving in random directions for hundreds of years. You can celebrate some kind of classically pagan Samhain thing. You can celebrate something that earnestly deals with whatever modern conception of death or horror [LW(p) · GW(p)] you care about. You can celebrate something in honor of whatever it is that you grew up with, arbitrary and/or commercial though it may be.

From my perspective, Halloween has a few different things going on. Some have to do with aesthetics, some have to do with "the functional/logistical form", and the two are blended together a bit.

Aesthetically, there's horror, death, autumn, and some manner of masquerade-ness.

Functionally/logistically, if you're doing 20th-century-American-style-suburban-halloween, there's interacting with your neighborhood in some way – either going door to door in costume getting treats, or having people come to your door and give treats out. In my conception of Halloween this part is at least 30% of the point.

I mentioned elsethread the two-sided-marketplace problem here. Some other things in that frame is that currently, community/neighborhood interaction seems on the decline (at least in neighborhoods I've been in), and this seems quite bad – we (where "we" means people with roughly my values) are in a rearguard fighting-retreat against atomic individualism corroding a lot of cultural cornerstones. A lot of those cultural cornerstones were actually bad and it's fine to let them go, but the process doesn't seem really aligned with any particular values.

Playing a Ravenloft one-shot is certainly another fine thing to do for Halloween, but if you were missing sense-of-neighborhood as part of the loss of Halloween, it won't help.

But if one cares about maintaining any sense of neighborhood, then it's especially valuable to look for activities one can do that take advantage of what remaining social institutions there are and reinforce/build off them.

Halloween caroling feels to me like a relatively natural evolution of the existing holiday elements (given that holidays evolve sort of randomly in the first place), and a healthier evolution than most of the ones that capitalism is prone to offer. It's easier to jump-start with random strangers because almost all of the elements are already familiar, and the one element that is new (for Halloween) is a borrowed element from Christmas.

What was really striking, going Halloween Harrowling yesterday, was how much the neighbors seemed deeply appreciated and excited* by it – it was one of the purest senses I've gotten of "going through town, spreading holiday cheer"

*unlike Christmas caroling, alas. The important, valuable distinction between Halloween and Christmas is that for Halloween, having lots of decorations in your yard is a strong signal that you actually want strangers coming to your house, which is not at all true for Christmas. Times I've went Christmas Caroling have felt fairly hit-or-miss for people actually appreciating it.