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Partly thanks to the wonderful blogs of Tony Dowler and Dyson Logos, I've found myself obsessed recently with the idea of building that epically classic D&D adventuring environment: the dangerous multi-level underground dungeon.

While I think the best way to go about it is to crack the ol' DM's guide open to the right section, sit down with papers and pencil and just start mapping away, are there any recommended guides or online discussion out there about undergoing this design project? Creativity tips, etc?

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One of the most brilliant analysis of dungeons was written by Melan and can be found on Enworld here.

He develops a technique of analyzing how various dungeon flows by using line diagrams. He uses it to analyze several newer and older dungeons including some classics. To summarize, dungeons that are laid out where their encounter proceed in a linear fashions are generally not as well like as those which branches and in his opinion the best dungeons are where the encounters are in various loops that allows the players the full freedom to pick where they go.

I have a post on minimal dungeons here as well as an example here. The basic gist is that if you look at what Arneson did (as shown in First Fantasy Campaign) and what Gygax did you find that what we think of as a module is an artifact of publishing tournament scenarios. What Gygax and Arneson actually used were little more than sketch notes with a only a few areas written in detail. They used random tables, general notes, and improvised as the players explored through the dungeon.

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If you zoom in the above image you will see that most rooms are single line descriptions. The same for Blackmoor in First Fantasy Campaign. From long experience it is tedious to make a dungeon and especially a megadungeon in tournament style. By using the minimal approach you can cover a lot of ground (or levels) within the time that most people have to prepare for games.

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That image is already at maximum resolution, so there is no zooming for me. –  Adam Dray Oct 12 '10 at 16:13
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First, as this is a very recent post, I recommend Sly Flourish's "Making Awesome Dungeons" as well as the classic 5 room dungeon concept.

5 room dungeons are perfectly adaptable to megadungeons: recursively create 5 room dungeons until you have "way too many" rooms.

Tool-wise, use Masterplan to create the adventure framework and PyMapper with resources from Dungeon_Tiles to make the physical structure.

Don't plot out the dungeon until you have the conceptual framework down, as without a conceptual framework, you'll end up with monster-closets without an interesting dungeon ecology.

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