This D&D Retreat Costs 10x a Chess Tournament

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 with a Google search 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.

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 to make a page like the above, 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
• Panel discussions

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.

I’ve noticed that, when I suggest brilliant ideas 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.