O'Malley.dev

My first time as a dungeon master

March 25, 2021

I recently ran my first Dungeons and Dragons game from behind the board. I spent the better part of a month setting up scenes in Roll20, reading the one-shot end to end and watching several people on youtube running the game to know what to expect. As far as I can tell a good time was had by all and I actually can’t wait to do it again even with the huge amount of time it required.

The prep

The one-shot I ran is called the Wolves of Welton. It’s a free module from Winghorn press for DnD 5e. In addition I read nearly all the Encounter of the Week posts on dndbeyond.com to get ideas of how things could be fit in should my players go off the rails.

As we were playing online over discord I elected to use Roll20 to give my players a virtual tabletop to better see encounters and interact with NPCs. For the maps I mainly got assets off Reddit and Pinterest linked to the Wolves of Welton

For character sheets I used dndbeyond.com in conjunction with the Beyond20 browser extension to allow my players to roll from their character sheets into Roll20 directly which saved a lot of setup hassle.

The game

The game was pretty standard, I’d originally budgeted 3-4 hours to complete the one-shot, But in total it took closer to 5. Additionally I had planned for 4-5 players in the game, but ended up with only 2 on the day. This was mostly due to me not setting a date and time for the game when I asked people to play and having to deal with a 9 hour difference in time zones for some players.

Some other thoughts

While reading the different encounters I noticed there’s a recurring theme to reference the equipment list in order to generate the inventory for stores in game. It was the only thing I didn’t find a tool for specifically which I found weird. There really should be an app for that.


Written by Scott O'Malley who writes code, loves his dog and is attempting to learn Portuguese. (Spelling mistakes are my own)