Bucket List Achievement: Finished a 6-year campaign ending at level 20

Back on November 24th, 2019, I sat down at a table with eight of my closest friends for a game of D&D. It was a simple enough beginning, a group of unrelated 3rd level travelers were roaming the city on a stormy night when out of the blue, a bolt of lightning struck a tiefling fighter in the city streets. Running to the scene of the commotion, the adventurers who would later be hailed as the Dusk Riders met for the very first time.

Over the next couple of years, my group experienced all manner of changes to our daily lives. For one, we all graduated high school, starting careers or going off to university to study. Several of us moved out of state, and the aforementioned tiefling’s player even had two children. There were times where we took a break as life and burnout happened, but never for too long. We somehow stuck together, making an effort to play every other week. There were incredible roleplay moments, both exciting and unnecessary combats, character deaths, character and player dropouts, and on at least two occasions, interventions to address concerns the players had with the campaign's pacing and narrative. Working together with my friends to write a story we could ALL enjoy, on March 8th, 2026, my campaign finally came to a close in the company of seven of those eight original players.

Ever since my first foray into DMing back in high school, one thing that I've always wanted to do was run that fabled level 20 campaign. To start from the bottom and follow a group of misfits as they changed the world one level at a time. I honestly didn't think we would make it. There were hiccups and mistakes along the way I'd made as a DM, and I was constantly concerned we'd drop the game as well had so many before. After all, this wasn't even my first time trying to DM this particular story.

My first attempt at a long-form game was back in what was probably 2016, an ambitious homebrew campaign in D&D 3.5 that I titled “The Six,” named after its eponymous six BBEGs. I made so many mistakes, abandoning the game after I realized I had written something that was far too railroady and underdeveloped, relying on the BBEGs to carry the story even though I had made them far too powerful for the party to meaningfully threaten.

Years later, with a couple more DMing experiences under my belt and using a new, more streamlined version of D&D with 5th edition, I decided to run it back. I had reworked the main villains, making ways to tie them into my PC's own backstories and toning down their power so the group didn't have to wait for level 10 to begin the main story. Even then, the group was probably about level 7 before they got their first taste of a BBEG, the hellcursed griffin Lord of Monsters, Shal'Khorizarr. I went into the game thinking it would last maybe two years. Boy was I wrong. 

I'm very thankful to my friends for sticking through to the end with me, it was an incredibly fun ride, bumps included. Level 20 combat is insane, especially when the group is able to Gate the final boss out of his lair and start the final battle on entirely their own terms. While many of the BBEGs had climactic deaths, it was hilarious to watch the mastermind behind everything die to bleed damage on his own turn, falling from the sky and crashing into the dirt. I wouldn't have had it any other way.

Here's to the Dusk Riders, you glorious fools. With my next game having started just last week, I look forward to taking all the lessons The Six taught me to make something even better.