25 Days of Wicked Good Christmas: Planning The Ultimate D&D Holiday Special

I’ve been playing Dungeons & Dragons with the same group of guys every week for the last five years (six in January). We’ve dabbled into Pathfinder, Pathfinder 2E, Star Wars Roleplaying, The ASOIAF RPG, and even one game system with giant mechs.

One thing that never changes, however is our annual “Holiday Special” around the table top. Each year, one of the three eligible DMs in the group (myself included) will craft a special one-shot session, complete with all kinds of holiday movie references, jokes, and a main focus on having some laughs and being merry.

Here’s a quick guide on how to plan your own. But first – you know the vibes. Buy a sweater, then enjoy the blog. It’s that simple!


The Night Itself

For our group, it’s not just the holiday session that makes the night important, it’s a night of traditions and time that we get to spend with each other. We try to keep the session itself pretty brief, so we’ll have time to just hang and joke around and have some laughs.

We also have two big annual traditions, our Secret Santa gift swap, and an annual reading of “The List”, which is a running list of hilarious, ridiculous, or just otherwise noteworthy quotes that have popped up around the table year over year. The list dates back to some of our very first sessions together, so it’s always a good source of laughs and nostalgia.

The Surroundings

I’d strongly recommend to decorate your game area and encourage folks to dress their part (with ugly sweaters, of course) if possible. If you’re planning on doing this in person, be sure to do so safely and responsibly.

Aside from making sure the “fire” is roaring in the background, usually I’ll throw on some seasonally appropriate music, and encourage folks to bring some treats for around the table. In the past I’ve made mulled boozy cider and wine, and we’ve had Christmas cookie crumbs everywhere by the end of the night.

Christmas Special Monster: Toy Eater for 5E : DnD

The Game

Of course, you’ll also need to get a game written for everyone to play! Here’s a few links below to get your creative juices flowing. Maybe Santa Claus is kidnapped by the Krampus or some Evil Snowman, maybe Santa is an imposter and your party needs to save Christmas from him!

Whatever the case may be, these stat blocks should help get you going in the right direction. When in doubt, just include a bunch of references to your favorite holiday movies, and everyone will have a great time.

Santa Claus – (5E Stat Block)

The Krampus – (5E Stat Block)

Evil Snowman – (5E Stat Block)

Adventure Sample – The Darkest Night (Tribality)

Adventure Sample – Krangel’s Workshop (DungeonMaster.com)


After you’ve read all this, I hope you feel as well equipped as you can be for your very own tabletop holiday special. It doesn’t matter what you celebrate, or what games you play – as long as you’re taking some time to appreciate the friends you have around you especially after this absolute nightmare of a year.

Happy gaming, and happy holidays my friends!

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Papa Dom

Co-founder, lead blogger, graphic designer, and manager of WGG's writing team - Dom has been writing about video games for over ten years. Dom's work has been featured on some of the world's biggest gaming news outlets - including Dexerto, GameInformer, and IGN.

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