13 Halloween Episodes to Kick Off the Holiday Special Season

October kicks off the holiday special viewing season. From now through to the new year, television shows will be featuring holiday specials. It's the festive activity I enjoy the most. And while most people will write about their favourite movies or series that are themed by the holiday, I wanted to highlight some of my favourite Halloween episodes. So here are 13 of those episodes I have loved over the years. 

Oooo, 13 - spooky.

A lot of shows focus on elements of the spooky season, such as Wednesday, Stranger Things or The Walking Dead. So for this list, I am focusing on episodes of some of my favourite shows that featured at least one Halloween episode. 

I am excluding specials like "It's the Great Pumpkin, Charlie Brown," which hurts me. But that was created as a separate special than an episode in a series. Even as a big fan of Peanuts (happy 75th anniversary of this, by the way), I could not include the "Great Pumpkin" segment from The Charlie Brown and Snoopy Show.

I hope this list causes waves and great debate. Use this list to create your own viewing schedule.

The Belcher kids debut their first ever costumes - Tina as a mommy mummy, Gene as Queen Latifah and Lousie as Edward Scissorhands. After a disappointing trip down their street, the kids take a ferry over to Kings Head Island. That's where the full bars are. But so are the teenagers who terrorize the younger kids who just want candy.

As a kid, I would keep an ear to the ground for full-size bars. Even king-size bars or cans of pop would be handed out. I miss trick-or-treating and having a better metabolism.

The study group attends one of Dean Pelton's dances. The Dean serves funky army rations to the students and causes a zombie outbreak. The study group tries to survive the mayhem, falling one-by-one to the infection. I love the multiple storylines within this episode, but mostly the ambiguity of both Shirley and Chang’s costumes. Hopefully this month, I will get to read one of those parts (or Troy) at “The Next Best Thing” Halloween Table Read, October 26 (check it out so I can win a prize).

Larry David being Larry David, questions two young girls about their age and lack of costume. I get it. Nowadays, I would not give candy to anyone who does not legitimately dress up. As a result, his yard and house are vandalized. This is why Halloween needs strict rules about costumes. Age should not limit us, but if your teen goes out, make sure they are not going as their “sister” or a “teacher.” Step it up, kids.

This episode should be called “The Only One with the Halloween Party.” I think Friends missed the mark with Halloween, but made up for it with Thanksgiving. 

This episode has what I hope would be at a party now: an arm wrestling match between a potato and a bunny, Supergirl facing off against Catwoman, and Joey dressed as “Chandler. Rachel is there too. It's the Halloween party that was promised to us young viewers, who didn't know if life would be that way. I thoroughly enjoy the Phoebe/Ursula storyline.

“The Haunted Mask” is a Goosebumps classic, both on the page and on the screen. Carly Beth purchases a rubber mask from a sketchy Halloween shop. The mask adapts to her face and she cannot get it off. It then starts to play with her mind as she weaves her way through the streets on Halloween night.

R.L. Stine got the idea from an instance when his son could not get a mask off his face. This episode reminds me of the freaky masks my dad kept in the basement and would put on, chasing us around. This is why Halloween masks aren't as popular now, not latex allergies or safety.

The first Halloween episode for Modern Family, Claire’s obsession with Halloween is showcased as she takes every step to scare her family. The Dunphys outfit their home as a haunted house for trick-or-treaters but each person has their own problem. It all comes to a head as Claire prepares them for a festive evening, only for each to want to back out. What is Cameron's over-the-top dramatics as he relives a childhood memory that puts him off Halloween. Also, Mitch as Spiderman while his new office does not celebrate the holiday.

Motherland is a BBC show that aired in 2022. If you have not watched it, all episodes are available on CBC Gem. The show's premise revolves around the lives of school parents and the balancing act of managing their lives. 

Series 2, episode 4, is "The Purge." School parents, Julia, Kevin, Liz and Anne, take their kids out trick-or-treating. They bring the kids of fellow mum, Amanda, who is busy sitting outside her shop dressed as a sexy nurse. As the night closes, they return to Kevin's for a party and think one of Amanda's kids is missing. When they return to the streets, the night has gone from family fun to teenage terror. 

Please watch Motherland. I need others to talk to about this.

What lengths would you go to to win over $15,000 in savings? Dunder Mifflin’s annual Halloween celebration reaches new heights of competition. The staff, except Oscar, believe the $15k to be the actual amount one wins. Given this, they take the contest seriously and most change their costumes to increase their chances to win. I wish I had a 2011 Scranton/Wilkes-Barre Coupon Book with over $15,000 in savings to give away. As the person who organizes these activities at work, I wonder what would be the prize my coworkers would compete for?

Leslie spends her night chasing high-school prankster, Greg Pikitis, with Andy and her cop boyfriend, Dave. The mind of this child plays against Leslie’s sensibility and he pulls off an epic prank in their office. Meanwhile, Ann throws a Halloween party that gets turnt by Tom. Ron sports his only Halloween costume, a pirate. While there are only three Halloween episodes in Parks, Ron wears the same costume in all three. This theory is sound - "this is my Halloween costume" - and I believe Ron and Dina from Superstore are out-of-state cousins.

Roseanne is the queen of Halloween. In "Trick Me Up, Trick Me Down" Roseanne and Dan don my favourite costume of theirs: Deadgar Bergen and Mortuary Snerd. The song and act are entertaining enough, especially when Roseanne rips on the fellow attendees. But the majority of the episode focuses on the rivalry between Roseanne and her neighbour, Kathy Bowman. After a murderously funny prank pulled on Kathy in the opening sequence, Roseanne is on constant pins and needles that Kathy will retaliate. Roseanne spends her night in the lodge following Kathy around. I really loved this dynamic and wish the Bowmans didn't leave so soon. We also get to see a short return of George Clooney as Booker, the Wellman Factory's former floor supervisor and ex-boyfriend of Jackie.

What ties it off is the snake prank the Conner kids pull on their parents and a failed prank organized by Dan and Jerry Bowman on Roseanne. Poor Becky thought she was just getting a new kitty. 

Halloween 1997 landed on a Friday. With this came the ultimate line-up for ABC's TGIF Frightful Halloween Bash. The line-up included Sabrina, as well as Boy Meets World, Teen Angel and You Wish. I am sure I recorded this line-up on a VHS to watch the next day, while bingeing on candy. 

Sabrina gets added to this list because "A River of Candy Corn Runs Through It" has all the makings for the best Halloween party ever. The party was created after Valerie told Libby and the school about Sabrina's party. Although Hilda and Zelda encourage it, the new furniture arrives and they talk. Along with Salem, their talking cat, the party goes on but not without spooky chaos. When will Heidi Klum recreate this moment and invite me? I could do without the river of candy corn though.

How do you choose just one Treehouse of Horrors? For me, a short jingle comes rings in my head: “Just don’t look. Just don’t look.” The “Attack of the 50-Foot Eyesores” is my favourite segment. Who hasn't envisioned iconic mascots and logos coming to life? The Zip Bros coming to life and dragging their head gets me every time. It's the Paul Anka guarantee.

The segment is followed up with “Nightmare on Evergreen Terrace” and “Homer3.” Both are wonderous in their own right, which help to round out my decision. Anything pre-Y2K could be on this list.

Superstore produced hauntingly hilarious Halloween episodes in its six-season run. “Sal’s Dead” wins my vote because of Cheyenne and Matteo. Cheyenne paints Matteo to look like Sal, the store worker who dies in the walls of Cloud 9. Matteo hopes to use the passport to go back to the Philippines for a wedding. But Matteo adopts the creepy personality of the deceased. Which is good, because Sal was a silent character but a strong one. The whole dealing with a dead body in the store adds another level of hilarity that makes me want to stop at Cloud 9 for a last-minute costume and candy.

What do you think? Do our picks align or are you thinking this was more of a trick than a treat? Leave a comment below or on my socials.