Every year I try to watch the simpsons newest halloween episode, the original halloween (1978) and the great pumpkin charlie brown special at least once.
Any shows other people try to watch during or around Halloween as a sort of ritual?
I try to catch at least one of the horror movie marathons.
The Thing, both Carpenter’s '82 version and the 2011 prequel.
Also like to pop them in (esp. the '82) if there’s a good winter storm outside at night. 
My grandson (now 12) and I watch Halloweentown (Disney) and Scary Godmother each year.
I try to watch a couple of the classic Universal horror movies. I have the Frankenstein and Dracula box sets.
The Nightmare Before Christmas. Then it comes out again for Christmas gift wrapping night.
For scary stuff, I know no movie that scares me so much as these two tv shows, so these are my “glass of wine and cuddle with the hubby and get scared” picks:
*Hush *from Buffy the Vampire Slayer.
*Blink * from Doctor Who.
I’m tempted to add Pan’s Labyrinth to the stack, but I’m not sure I’m ready to see it again. I’m not sure I’ll ever be ready to see it again.
The Garfield Halloween special, although I haven’t seen it in years/decades.
“Candy…candy…candycandycandycandy!”
My wife watches Hocus Pocus each year.
This is a really great question. Everyone has his/her fav Christmas movies-- why not Halloween movies?
I’m not into gory, scary movies that scare you just for the hell of it (what Joe Bob Briggs called “teenage pork chop movies”). And I really don’t like seriously scary movies like The Exorcist. I like something more subtle and atmosphere-y. Just saw The Awakening, and liked it a lot. Also The Others (Nicole Kidman). And one of my all time favorites, Halloween or not, the 1944 The Uninvited.
I saw that as a kid! Loved it. To answer the OP:
The Great Pumpkin.
Scooby doo meets Kiss. Either I’m just a dirty old man or that particular cartoon has some double entendres that aren’t exactly kid appropriate.
I am not a big horror fan, so the only one i catch each year is “It’s the great pumpkin, Charlie Brown!”
I really dislike the Simpsons Halloween specials, even though they are popular and i generally like the the Simpsons.
Charlie Brown is a perfect special, and hasn’t become stale in over 40 years.
The Nightmare Before Christmas - always
Other than that, in the weeks/days leading up to Halloween, I usually try to watch a few horror movies I haven’t seen before.
I’ll totally watch The Great Pumpkin if I know when it’s on and it fits my schedule so I can.
I make it point to watch Dawn of the Dead every Halloween, late at night, after the tricks have been treated and the pumpkins blown out. Romero version, not the “remake”.
I was trying to watch Halloween (Carpenter’s, not the Rob Zombie garbage) each Halloween as well, but last year didn’t, instead went with Halloween 2 (again, not the Rob Zombie atrocity).
I’d really like to catch some of the old Universal and Hammer flicks, but they rarely get played anymore, and when they do it’s usually in a timeslot that doesn’t work for me or my DVR. Doesn’t help that fall TV has started so I have less time to fit in Halloween stuff than I’d like (rarely have this problem with Christmas time since most shows are off then).
Also love it when the Treehouse of Horrors start hitting the local Simpsons reruns. Last year they started really fucking late, so barely got to see any, but this year they started a bit earlier, so that’s good. Still not early enough that they can show all of them, though…
I like all the old classic horror movies, if they don’t run the old Hammer and Universal stuff I will dig out my DVDs of them. Especially stuff like The Raven, The Mummy, Dracula - though I also really like catching Psycho, The Haunting of Hell House, stuff from the 60s and 70s. Occasionally we will get lucky and they will show the 80’s horror stuff, original Carpenter stuff, not the remakes.
30 Days of Night
I have the DVD of this pre-ordered from Amazon and hope it will arrive before Halloween.
Not the same things every year, but around the end of October my thoughts turn to Kolchak: The Night Stalker series or the goofy-bad non-Hammer horror movies starring Peter Cushing and/or Christopher Lee–Horror Express, The Skull, Blood Beast Terror.
Plan 9 from Outer Space is a Halloween tradition in our house.
A friend/ex-roommate from undergrad made a tradition out of The Crow; I’m not quite so religious about it, but I do make something of an effort. Also fond of getting Arsenic and Old Lace in somewhere around there if I can.