This D&D Retreat Costs 10x a Chess Tournament
They're always sold out
This week I want to look at an example from outside of chess that could point the way towards a kind of tournament that’s much more enjoyable for players and much more sustainable for organizers. That event is D&D in a Castle. In their own words, “D&D in a Castle is a 4-day luxury, all-inclusive tabletop gaming retreat.”
One of their 4-day vacations in the US starts at $3,250. In contrast, the similarly long World Open chess tournament costs $318, less than 10x as much. Yet D&D in a Castle consistently sells out their events.
Dungeons and Dragons is a fantasy roleplaying game. Unlike chess, which is a competitive one-on-one game, D&D is more about collaborative group storytelling.
Frankly, it’s not my thing. I’m much more interested in crushing an opponent than telling a story in a group. Nonetheless, chess tournament organizers could learn a lot from this event.
Focus on Experience
It’s in a CASTLE!!! The only chess tournament in a castle I could find was this one in the Weissenhaus castle on the Baltic coast. (Shoutout to the Chess Castle of Minnesota, but it’s not a real castle. It’s next to a Macy’s.)
But why not more? It’s on theme, right?
As a commenter on my previous post wrote, “There are thousands of us looking for the old-fashioned (and probably mythical) wood-panelled club room.”
It doesn’t have to be a castle, but by focusing on ambience, organizers could set their tournaments apart.
Promote Personalities
D&D in a Castle has a page dedicated to promoting their Dungeon Masters (game leaders).
Unfortunately, someone has already taken the Chess.com screen name DungeonDad, but they never played a single game. Thanks for ruining it for everyone!!
But seriously, chess has a natural advantage here. Chess grandmasters and content creators are already celebrities. Imagine if when you went to a tournament, you could play in a simul with Eric Rosen, or attend a talk by Jennifer Shahade.
Some tournaments have started partnering with streamers, but there’s a lot more room to partner with and promote appealing chess personalities. What I’m trying to say is that, for $10,000, I’ll come to your chess tournament.1
Professional Website
Compare D&D in a Castle’s website to this:
I’m confused how it’s even possible to make a website that looks like this in 2025. If you use a website builder like Squarespace or Wix, it will automatically format your page to look decent. So you have to know enough to write custom HTML, but also totally disregard styling and design.
I actually find it charming that chess tournament websites look like something from 1995, but I already know what I’m signing up for. If someone is on the fence about playing their first tournament and the website looks like this, they’re not going to sign up.
With the tools mentioned above, it’s easy for an individual with no coding experience to make a professional looking website in a few hours. There’s no reason not to do this.
Side Quests
At D&D in a Castle, “guests can choose between One-Shot games and other Side Quests, such as game-related crafting, workshops, panels and outdoor games.”
Chess tournaments can and should have more side events. These could include:
Smaller, faster side tournaments (blitz, bughouse, etc.)
Classes or lectures
Author signing or talks
Simuls
Parties or happy hours
These events don’t need to replace a single “main event”, but could run alongside it, for those who want something in addition to/in place of a single, massive tournament. The schedule should have enough slack that it’s possible to fit in events like this.
The Las Vegas Chess Festival has done a great job introducing additional events like these. More tournaments should follow their lead.
Wrapping Up
I’ve noticed that, when I suggest a brilliant idea like this, I’m often misunderstood. So just to be clear, here are things I’m not saying:
Everyone should quit chess and play D&D.
All chess tournaments should cost thousands of dollars.
You have to try to make as much money as possible.
Chess shouldn’t be competitive.
What I am saying is this: if chess organizers are willing to think outside the box about what a tournament looks like, they can create experiences that are radically more appealing for many players.
I’m willing to negotiate on the price.
I have actually organized tournaments at a castle it’s not easy since castles aren’t usually in urban areas it’s hard to get people to make the trip before you have become a known for creating great experiences for the players. I created this sort of of social equity by running tournaments at my house where people would play on the 3rd floor and I would have the main floor set up for skittles and the yard would have a tent and tables and chairs a giant chess sets but the main thing that I did was cook for everyone what that did was create a situation where people hung out between rounds a got to know each other instead for just racing off to get food. Before I stopped doing them I was getting 30/40 people to my house to play or just hangout it even got super strong a lot of times with a few masters and a handful of of experts! I would say if you don’t see the tournament you want make it!
This is a smart take, as usual. I especially like the non-gratuitous shots at the registration aesthetics. So on point. The whole enterprise is ripe for someone with time and money to come along, operate at scale (always the issue in US chess), and drag matters into the 21st century, even as something intangible will be lost. Maybe chess.com can form a subsidiary, chess.rl (as in Real Life), which doesn't actually exist as a top-level domain, but I like how it sounds....
I wonder how age dynamics feed the status quo; I also wonder how the cooperative nature of D&D as opposed to the zero-sum nature of chess skews the participant sample. I would also bet that the percentage of casual players who attend four-day D&D events is vanishingly small.
So much of the chess tournament scene in the US consists of hyper-competitive scholastic players, and often very young scholastic players, many of whom are focused and driven, even if much of the focus and drive comes from their parents. D&D, meanwhile, is a curious mix of Gen X and Millennial adults colliding with Stranger-Things-boom kids, and surely it's the former who drive events like D&D in a Castle.
All of this is fun to discuss but largely academic to me, as I'm of an age and temperament that liked chess better when it was small, when it was a serious intellectual enterprise of you wanted it to be but was ultimately just a board game. I feel that now it takes itself very seriously indeed, perhaps unsurprising given the amount of money involved. Listening to DR talk about anti-cheating measures at chessdotcom the other day, you would have thought he was talking about heart surgery or feeding the hungry. Something similar has happened in baseball, etc. And if you thiknk things are bad now, just wait until gambling comes. You'll have on-screen, in-game parlays and prop bets. It's a brave new world.