Running Tabletop Games with Obsidian

I love Obsidian. I'm writing this post in my main Obsidian vault right now, actually. You should check it out for yourself, but in brief, Obsidian is a very powerful notes management application with document linking, among a bunch of other great features.

I also love playing tabletop RPG games. My current favorite game is Quest, but I mostly play D&D 5th edition. Specifically, I mostly DM when I play, and I've constantly been searching for an actually good digital DMing setup.

It wasn't until after I had already begun building my own app specifically for DMing that I found Obsidian, which basically did everything I was planning to build. Though it does lack some of the features I wanted, but still, it was enough to make me stop what I was building and find a way to work with it. Let's run through my process and why Obsidian is so dang good for DMing.

I'll preface this by saying I mostly run custom campaigns in custom worlds, but I believe even without having a trove of your own custom written content, Obsidian proves useful.

Features

...and why they're good for DMing

Reference

The real key to it all though is having a wealth of resources available as a baseline for building adventures and referencing during gameplay. I found a really great markdown version of the D&D's rulebooks and wrote a script to break it down into individual documents. One document per spell, class, mechanic, item, monster, etc – with a few Obsidian bonuses like backlinking to indexes for spells or monsters.

Then, I just plop all of that in a folder called reference, and make an Obsidian vault with that folder. Suddenly, I have almost all of D&D's content at my request with just a simple file search, fuzzy find, or document link. When I say there is a goblin in a scene, I can just link to the document with all the info about goblins with [[goblin]] in my Obsidian documents.

Not to mention that Obsidian lets you embed a document in another document, so you can directly embed any reference page into your writing for quick access.

You can download a copy of my Obsidian D&D 5e reference folder. I will be continuing to iterate on this and will make a for real repo in the future but for now, that's what I'm working with. (Update: there is now a github repo: twisterghost/5e-obsidian)

Additional Files

I then have a few auxiliary files on top of the campaign writing and the reference documents.

And that's about it! Not much else to say. The ideal app, the one I wanted to build, is basically Obsidian, but also would have an automated turn tracker, dice roller, and maybe even a virtual tabletop. I know Roll20 has a lot of tools, but in my experience, it ends up being a mess to work with, especially when trying to fiddle with it all in real time while DMing. But for now, Obsidian has been the closest I've found to my ideal setup.