5 Great Disney Halloween Specials and Movies You Rarely See

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Growing up I would get so excited from October through December. Holiday decorations went up from month to month and all the Halloween and Christmas shows would be on. We would have either amazing costumes my mom made or we would go and get our Ben Cooper costumes in the box from Ames or Jamesway. I still miss those costumes and I will always remember that smell (if you were a kid when I was you know what I’m talking about.)

But I always loved the Halloween specials or movies you would see on the Disney Channel. Here are five of my favorites growing up. Some you still see, most you don’t and you can’t even find officially anymore.

  1. Ichabod Crane and The Legend of Sleepy Hollow

This year marks the 70th Anniversary of this Disney special.

This classic Disney film was 1/2 of a set Disney did called The Adventures of Ichabod and Mr. Toad (1949.)

The first half of the movie was based on the 1908, The Wind in the Willows book, and the second half, was based off of Washington Irving’s short story The Legend of Sleepy Hollow (1820.)

I grew up waiting for this one. It’s not as uncommon as other ones on the list.

The Legend of Sleepy Hollow is the story of a school master named Ichabod Crane.  He decides that he wants to woo and marry the wealthy farmer’s daughter Katrina Van Tassel.  But, the town hero Brom Bones also has his sights set on Katrina.  During the Van Tassel Halloween party Brom notices how superstitious Ichabod acts and deliberately chooses to  tell the frightening story of the Headless Horseman.  Talking about how he is after your head, but if you can cross the bridge he will disappear.

Of course after Ichabod leave the party he encounters the specter.

The story is still so popular that Disney rides the Headless Horseman through the Magic Kingdom before the Boo To You Parade during Mickey’s Not So Scary Halloween Party.

2. Mr. Boogedy

Mr. Boogedy was a 1986 made for TV special that aired as “The Disney Sunday Movie.”

It was about a joke store salesman named Carlton Davis (Richard Masur) who, with his family, moved to the town of Lucifer Falls, New England to open a new gag store.  He was with his wife Eloise (Mimi Kennedy) and their three children, Jennifer (Kristy Swanson), Corwin (Davis Faustino), and Aurie (Benjamin Gregory.)

After they get to their new house they meet “old man Witherspoon” (John Astin) who tells them a tale about how the house is haunted by three spirits: Mr. Boogedy (Howard Witt), a woman named Widow Marion(Katherine Kelly Lang) and her son Jonathan (Jaimie McEnnan).

Mr. Boogedy and Jonathan are inside the house but the Widow Marion can’t get inside to him because Boogedy is keeping them apart.

How did they become ghosts? Well Mr. Boogedy (who was once Mr. William Hanover) was in love Marian and sold his soul to the Devil for a magic cloak. Hanover tried to cast a spell he blew up his house with him, Marion, and Jonathan in it. Which is why they are ghosts haunting that location.

I’m not going to tell you anymore of the story but it’s a fun movie.  Good news! It and my next one are coming to Disney+ when it launches in November!

3. Bride of Boogedy

Of course the first one did so well that they made a second one!  This one was released in 1987 and has most of the same cast. With Jennifer (Tammy Laurnen,) Aurie (Joshua Rudoy,) Jonathan, and  Mr. Witherspoon (Leonard Frey) being replaced.

It is also about a year after the original film in the movie’s timeline. The Davis family has settled in and are doing great. Everyone seems to like them, except for the General Store Owner, Tom Lynch (Eugene Levy.)  Mr. Lynch is a bit upset that Carlton has been named the honorary mayor of Lucifest and he was always honorary mayor of the festival.

It all seems okay, but then the kids start to sense Mr. Boogedy again and he’s now he’s haunting them in their dreams. The parents blow it off, which I never understood after what happened just the year before.  They don’t listen even when the local fortune teller Madeleinska (Karen Kondazain) tries to warn Mr. and Mrs. Davis.  The parents even go as far as to stage a “fake seance” to prove them all wrong. But Mr. Boogedy wants his cloak.

If you want to watch this one you will be in luck as it is also coming to Disney + (but not till after Halloween when it launches in November.)

4. Disney’s Halloween Treat / A Disney Halloween

Still one of my favorite Disney Halloween-time memories is this special. Well it was two different, yet very similar specials.

The first version was called Disney’s Halloween Treat -1982. It was narrated by a Jack-o-lantern puppet (Hal Douglas) and it was made up of various Disney shorts that were Halloween themed or considered “scary.”

A year later in 1983, the second version called A Disney Halloween aired and it combined elements of the Disney’s Halloween Treat and Disney’s Greatest Villains (1977.)  This is the one most of us remember as it ran until the mid 90’s.  Sadly neither version are on the list for Disney+..YET.  (Get on that Disney.)

Some of the various segments included were:

  • Mad Madame Mim- The Sword in the Stone
  • Chernabog –Night on Bald Mountain- Fantasia
  • The Old Mill
  • Donald Duck and The Gorilla
  • Puss Cafe
  • Heffalumps and Woozles – Winnie the Pooh
  • Pluto’s Judgement- 3 shows put together
  • Si and Am- Lady and the Tramp
  • Peter Pan and Captain Hook
  • Several more Villain segments
  • 1937 Lonesome Ghosts with Mickey, Donald, and Goofy
  • But my personal favorite was the (1952) Trick or Treat with Donald, Huey, Dewie, Louie, and Witch Hazel.

5. Child of Glass

This one is a bit obscure but I remember watching it when I was little.

The Child of Glass is a movie from 1978 as part of the Wonderful World of Disney show. It was based on the book The Ghost Belonged to Me.

A boy named Alexander Armsworth (Steve Shaw), his parents Emily (Barbara Barry) and Joe (Biff McGuire) and his older sister Connie Sue (Denise Nickerson) move into an old Louisiana mansion.  His mother has been dreaming about restoring one of the old southern plantations homes.  So they move in to fix up the former home of river pirate Jacques Dumaine (David Hurst.)

Not long after moving in Alexander sees a light in the barn and goes up into the loft where he sees a little dog and  a ghost girl named Inez Dumaine (Olivia Barash), the niece of Jacques Dumaine.   She tells him that she can’t reunite with her parents because her uncle cursed her to wander the Earth when she wouldn’t tell him where her parent’s hid their treasure.

She asks Alexander to solve a riddle and break her curse.  But they only have a short amount of time to do so. The movie is about him solving the riddle and other issues that pop up with an unsavory living character as well.

Like I said earlier, this one is not easy to come by.

There are five Halloween specials I remember on Disney growing up. Another one I remember, but didn’t include was Watcher in the Woods. Also a great one to check out. There is a new version from 2017 as well.

What do you think? Comment and let us know!

Source: Myself from another article I did.

Disney has been a big part of my life for years--from family trips to WDW to growing up on Disney classics, TV, and movies. I'm a mom and an art teacher. I love to share my love for Disney and I'm also a co-host of the Disney fan podcast and YouTube Pirates and Princesses (PNP) channel. Also contributor D-Rezzed and Former contributor and acting social media manager at The Kingdom Insider. Opinions are all mine.