It's The Great Pumpkin, Charlie Brown
Charles Schulz's beloved Halloween special that first aired on CBS, on October 27, 1966. It features Charlie Brown and the rest of the Peanuts gang joining in the Halloween festivities, except for Linus and Sally who wait in the pumpkin patch for "The Great Pumpkin".
The Halloween Tree
The animated reimagining of Ray Bradbury's novel of the same title. Admittedly, I missed this as a child. It first aired in 1993, I can still remember the promos at the time. Being six years old that year, I think the imagery of the corpse-like Moundshroud flying about the screen was probably too spooky for me.
However, I finally gave it a watch this year and loved it. If you've never seen it before, it's a simple story about a group of kids that go on an adventure back in time to discover the roots of Halloween while trying to save their friend in the process.
Halloween is Grinch Night
This is definitely one of my favorite Halloween cartoons of all time. The story created by Dr. Seuss was made into an animated feature in 1977. Interestingly enough, it was supposed to be the prequel to The Grinch Saves Christmas.
The story follows a young Who named Euchariah who finds himself lost on Mount Crumpit after trying to go to the "euphamism", (the outhouse). When he encounters the Grinch he braves the terrors of the "paraphernalia wagon" in order to save the town of Whoville.
The Legend of Sleepy Hollow
Disney's 1949 animated rendition of Washington Irving's famous tale. It has always been one of my personal favorites to watch on Halloween. Bing Crosby narrates the story of Ichabod Crane and his ghastly encounter with the headless horseman.
Donald Duck's Scary Tales
This is definitely a treat for anyone who loves vintage disney animation. I used to have it on VHS and made it a point to watch it every year along with Disney's Haunted Haunts. It features three stories: Donald Duck and the Gorilla, Duck Pimples, and Donald's Lucky Day. As far as I'm aware it's not yet available on DVD, but you can watch them for free on YouTube.
The Pumpkin Who Couldn't Smile
This Raggedy Ann and Andy Halloween special was produced by Chuck Jones and first aired on October 31, 1979. It's a cute little story where the Raggedy siblings unite a lonely boy with a sad pumpkin teaching everyone the true spirit of Halloween.
Garfield's Halloween Adventure
Unfortunately, this is yet another one I missed as a kid. I was never really much of a Garfield fan growing up, but this one definitely deserves a spot on this list. In the story, Garfield cons Odie into accompanying him for trick-or-treating in the hopes that he'll get double the candy. When Garfield's greed gets the better of him, they both wind up in a spooky old mansion haunted by pirate ghosts.
The Nightmare Before Christmas
No list would be complete without this classic. I remember seeing this when this was released in theaters way back in 1993. This is undoubtedly Tim Burton's most famous animated feature, and is always fun to revisit around this time of year.