I wish I could put my finger on exactly what it is I love about Halloween.
It is my dad’s birthday, so there was always an extra special sheen to it. In our family birthdays were major holidays with full celebrations, so to know the day would end with cake was always nice.
I am a security freak. I hoard things; even now we have a cupboard in our house called “candy mountain” where I stash various candies, 98% of which never get eaten by me. The feeling of having it there if I want it is actually more satisfying to me than the taste of the candy. So of course any holiday where I could procure lots of candy (a rarity during my childhood in the 1970s) left me feeling very contented.
I am a sucker for coziness. The harsher the weather outside, the more cozy I feel in my home. Halloween, with its gray rain and undercurrent of chill makes reading in front of the fire all the sweeter.
I love the feeling of “holiday”–where everyone is in a certain sort of special frame of mind. It’s not a very tangible thing all the time but there is enough of a sense of it that it makes the coziness and contentedness feel amplified by societal peace.
Spooky things draw me, as does water. It’s not that I like to be scared; I just like the philosophical ideas behind ghosts. I like to ponder what ghosts are. And the “Halloween ghosts”–white blobs with eyes and smiles–are not regular ghosts to my mind. To me, haunted houses and those Halloween Ghosts are external pictures of my internal mind. It’s what it feels like to always be accompanied by other stories that didn’t happen here but happen vividly in your mind. Happy stories, but transparent and less tangible than reality. I think that’s why I like ghosts.
And then there’s Harry Potter. To me they go together, Harry and Halloween. Not for the obvious “it’s about witches and so is Halloween” nonsense that puts a certain brand of cultural Christian on the offensive. Back in 2000 I had an abusive boss–literally physically abusive as well as emotionally–and a large part of what got me through those seven months from February to early October was the fictional families in Laurie King’s Mary Holmes novels and then Harry Potter, which I read for the first time that year. And the second, third, fourth…etc. I quit the job with a settlement in early October. By mid-October I had what was pretty close to a dream job for me, and I still had Harry. The surrogate family of fiction kept me strong inside.
So those are all the pieces of the puzzle, I think, as to why I love Halloween so much. If you’ll excuse me, it’s time to go dive into Chamber of Secrets.
Just Another Pretty Farce 
I think I love Halloween for a pretty wide variety of reasons. For one, it really is the holiday for creatives. I mean, you absolutely can bring lots of creativity to other holidays, but what are the mainstays of Halloween? Costuming, Pumpkin Carving (sculpture), Ghost Storytelling. All creative ventures.
While I don’t wear it on my sleeve (you certainly won’t see me with powdered skin wearing all black), I do have a kind of fascination with the macabre, and fear in general. I can’t totally explain why. I think, in part, it’s because it’s such a big part of the human experience yet it’s one that is kept somewhat taboo. Why not explore and celebrate it in a safe, fun fashion? Oh, and I DO like to be scared. In a safe and controlled environment, I find fear to be fun. It’s why I ride roller-coasters and watch scary movies. I hear people say, “I like horror films, but they don’t scare me.” To each his own, but I don’t understand that. If a horror film can’t scare me, what’s the point?
Interestingly, I rarely wear costume, but what a neat thing it is. For one night you get to put on the role of pretty much anything you can imagine. How cool is that?
Also, it’s kind of the kick-off to the whole major holiday season. The “holiday” feeling you talk about starts with Halloween and then lasts for the rest of the year.