This doesn't really address the concerns in the OP but I wanted to note: I had struggled a lot to figure out what to do with Halloween as a childless adult.
Halloween costume parties are fun if you like making costumes, but... I dunno, didn't feel much connection to the holiday. The most exciting things about adult-halloween-parties are a certain kind of free debauchery that I'm not really into.
So I was delighted when a friend of mine invented Halloween Caroling, where you dress up and go trick-or-treating, except that you go to houses with lots of decorations (which are sort of self-selected for being open-to-experience), and ask they'd like a Halloween Carol, and then sing, like, Thriller or Addams Family or the Nightmare Before Christmas songs, and/or some spookier folk songs. It adds a sense of purpose to the holiday that... well, sure still doesn't really have much to do with Facing Death Squarely in the Face but is fun.
Isn’t another option just to do… nothing with Halloween?
I mean, there’s no law that says you have to participate in any given holiday, right? If you can’t think of anything to do that feels worthwhile, just… do what you’d do on any other day.
(I know you said you’ve now solved your problem, so consider this comment addressed to your hypothetical past self and/or anyone else who feels similarly to your past self.)
EDIT: Another, more ‘constructive’ (I guess?) suggestion is to do something that is Halloween-themed in content, despite being largely unrelated to Halloween in form. For example, you could get together with friends and bake some cookies shaped like ghosts or something, and watch some horror movies. Or, if you’re into D&D, you could (and this is something I’ve heard of a few people doing) run the Ravenloft adventure (perhaps the most famous horror-genre adventure module). Or anything else in this vein.
[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 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.
If anyone actually wants to contend with death this holiday season, I know a ritual-guy (I think in Austin Texas?) who is putting together an experience where he ferries you across a river to an island in a small boat, and then you crawl into a coffin, close the lid, and you hear some shoveling and a small bit of a dirt. You stay there for about 15 minutes reflecting on your life, and then re-emerge.
It was different not so long ago. When I was a child in the Midwest (mid-80s through at least the mid-90s), Halloween had a lot more tradition and ritual to it, but these rituals have been systematically curtailed or banned (I now live in the South, and the same is true here). Trick or treating used to be long and elaborate, treats were more commonly homemade and also elaborate, and costumes and decorations were more explicitly focused on fear and death. Halloween was about community participating in rituals of fear.
In the meantime the average age of homeowners increased, the population of children fell, and the general level of anxiety in the population increased. The entertainment industry diversified, and now even if you have cable there won't be a string of horror movies everyone watches. A whole genre of scary films, suspense, effectively disappeared in the meantime. Halloween traditions died by trivial inconveniences. Since the community aspects collapsed, new elements filled the void; entertainment entire shifted more towards adrenaline, comedy and sex; children's entertainment became increasingly nonsensical and averse to serious things; costumes followed suit.
Halloween was my favorite holiday when I was a child, but most of that is gone and now my child shall have only the memories my wife and I can impart. This saddens me greatly.
Huh, this comment leads me to look at Halloween through the inadequate equilibria lens.
Holidays vary in how much they're a community affair, vs family affair. Many (most?) of them at least aspire somewhat to be a community affair, but in a way that gracefully scales down when you only are doing it with your immediate family or friends. There are Thanksgiving Parades and Midnight Christmas vigils, but the holidays still basically work if you decide to do the unilaterally.
Not so with Halloween – it specifically depends on a particular kind of neighborhood, with a two sided marketplace between children and host-families.
I don't know whether Halloween really does help people come to terms with death, or anything like that, by coupling it with absurdity, but I don't think "we don't do standup comedy at funerals, so we don't really believe in meeting death with absurdity" is an argument that holds much water. Standup comedy at funerals runs the risk of offending (perhaps very severely) individuals associated with the deceased party. (And in some parts of our culture there is something not altogether unlike that: consider the old joke that the difference between an Australian wedding and an Australian funeral is that there's one drunk fewer at the funeral. Funerals and wakes can be pretty rowdy.)
Leonard Cohen on his poetic voice:
This is apparently exactly the opposite of how most people in the American world feel at this time of year. The great inevitable defeat should be expressed with electronically jeering plastic skeletons, humorous fake corpses, faux-threatening gravestones, and—let’s not forget the violence and disease responsible for so many deaths—generous fake blood, vomit, and slime. The celebration should be not only frivolous and ugly to the max, but really go hard on minimizing dignity! Don’t just dress as a fun ugly corpse, make it a sexually depraved fun ugly corpse!
Isn’t this just a bit weird? For instance, how is this good?
I’ve heard a couple of times something like: “Halloween is nice because it is rebellious, and a relief from all that seriousness. People usually treat these things with sacredness and somberness, and it’s a lot to deal with.”
If that’s what it is, would it also be cool if we incorporated more second-rate stand up comedy routines and pranks into funerals? Or had more fun smallpox themed parties?
I don’t think people do actually contend with death or horror in a more comfortable way via Halloween, for the most part. My guess is that they basically don’t think about the content of what they are doing, and just get used to hunting for bargain plastic corpse babies to put on their lawns, and laughing with each other about how realistic and gruesome they are. Which seems more like desensitization than coming to terms with a thing. Which I doubt is a good kind of relief from seriousness.
Also, if we are going to have a change of mood break around the potential horrors of life, the alternate feelings and purposes Halloween suggests just don’t seem very good. ‘Trick or treat?’ Cheap malice or cheap hedonism? Quick, find a huge mound of junk food, I forgot because I’m very competitive about drunkenly parading my buttocks in a way that makes me seem clever..
I’m obviously missing something, and I don’t actually blame anyone much within reason for getting into the holidays of their culture, but come on culture, what is this?