How to GM your first game on Roll 20

Setting up my new game in Roll20.

I’ve run a lot of games. I’ve never run one online.

Lately, it’s been hard getting everyone together in my D&D group. So in the interest of gathering together people with kids, people with busy schedules and people who travel for work, we decided to do our next session on Roll20.

The digital gaming platform is one we’ve used many times. John Bunger runs his Douglas & Dragons and Pathgrinders podcast games on Roll20, and I’ve played quite a few times.

But I had no idea where to start to GM a game of my own. With a little help from John, lots of forum posts and a ton of helpful videos on Roll20 itself, I’m ready to go.

Here’s my advice for fellow first-timers.

Prepare just like playing on your kitchen table. What would you bring to the game table if you playing in person? Probably books, notes, miniatures, maps, music and monster stats, to name a few. You’re going to need all of those here, too. Some will be digital (like your maps and tokens). But you’ll also want sourcebooks, adventure material and whatever else.

A lot of Roll20 is free. It’s free for players. It’s free for the GM. There’s lots of free art. There’s lots of free tokens.

OK, now watch this video: This one right here. We’ll wait. By the time you’re done, you should have a great grasp of how to set up your game.

Gather your art. Roll20 is a digital tabletop. You’re going to need art. But don’t panic! You don’t need to draw a map or anything like that. If you have digital copies of maps already, you can upload them easily. If you have a great printed map, scan it or lay it out flat and snap a picture with your phone. You’ll also need tokens to represent PCs and monsters.

You don’t have to buy maps or tokens. Roll20 does have tons of awesome digital tokens and maps for sale on its marketplace. If you want something well-made and ready to use, go nuts. But you don’t have to buy stuff if you don’t want to. Do a Google search for whatever character or monster you need, and then go make a token. RPTools offers a free token tool right here. Need a map for a forest encounter? Do a search “forest map RPG” and see what comes up. Or visit somewhere like the BattleMaps subreddit. There’s tons of free art online, and Roll20 even has links on its Game Resources page.

Roll20 has a ton of great videos. Watch them. There is a great list of  tutorials (with links to videos) on the site’s wiki.

Get your friends to sign up. The nice thing about Roll20 is that it’s free. Even for GMs. (Though if you’re running a lot of games and want access to some cool features, it’s not much to upgrade to a “pro” account.) Tell your pals to head to the site and sign up. Send them the link to your game (it’s in the chat window every time you log in). Then they need to input their character details into a character sheet. It’s easy.

Prepare your first session. First, you’ll need a map. Then you’ll need tokens for each PC. Then you’ll need tokens for the monsters. Create character sheets for your players. Input monster stats like HP and AC (if you want). Send the game group the link. Get started.

Ask questions. If you’re friendly with gamers, one of them has probably played on Roll20. If not, the site has a great forum. Ask whatever questions you might have, and they’ll be answered.

Set up as much as you can. You can pretty easily drop a map into Roll20 on the fly, but it helps if you have it prepared in advance. If you’re the GM, you can set up multiple pages. I’m setting up all the possibilities for our adventure, which I’ll detail below.


I’m running D&D’s Curse of Strahd.

(Spoilers ahead for anyone in my gaming group or who hasn’t played the adventure yet.)

At our last session, the players had just finished the Death House portion of the adventure.

Once the PCs exit the haunted house, they’ll be in the town of Barovia.

There’s a few ways they can go now. I’m sure they’ll explore the town, and they’ll find the tavern, the home of Mad Mary, the mercantile, the Burgomaster’s House and the church.

There’s also the possibility of random encounters.

So, I have set up our game in Roll20 thusly:

  • One page depicting the town of Barovia, both as sort of a holding area (so the players can’t see where they’re going next) and so they can navigate the town.
  • One page depicting the church.
  • One page depicting a road, for random encounters.
  • One page depicting a street scene, for random encounters.
  • One page depicting the Tser Pool Encampment, where Madam Eva lives.

In the places where there are monsters or NPCs, I have added those in the spots they’ll find them. I added in one NPC’s full character sheet since he’ll likely accompany them, but I only input HP and AC for the monsters they’ll face. I’ll have all the Monster Manual entries in front of me at home for attacks and such.






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