I had come across Castle Oldskull before, and finally picked up The Classic Dungeon Design Guide (and many others) due to the sale.

This book has got to be my favorite of the bunch.

I am currently running though a random dungeon with this, using bits from the Guide and Traps books, solo with Scarlet Heroes rules and having a total blast!

Like someone else said this is much like a hyper version of the 4AD generation rules, with access to a lot more detail you might want for a full RPG. Should I survive/ever get bored of the dungeon I'll probably take the same hero through some city-state encounters and perhaps use the Adventure and World Generators to see where that takes me.

Kent David Kelly has done a great job with these books.

If I had to sum this up in a few words, they'd be "Comprehensive and potentially cumbersome." This generator can cover all the bases of a dungeon's generation from corridor to corridor, room by room, from size to the contents within. It gives detailed descriptions from a first person perspective, using precise measurements that easily snap to a grid. If you go entirely by this book to set up the contents of each room, you might roll some pretty special stuff to put in, but the process will slow to a crawl as you jump to and fro throughout the book.

I would've appreciated more images for the corridors and room sizes rather than plain text, but since its descriptions work hard to ensure you actually get the image the author intended, I'll have to settle for that. It is also appreciated to have sections clearly numbered and referenced throughout the book, making it easy to find where you need to go.

For those of you looking for a on-the-fly map generator, this is an excellent option.

Today I soloed my way through Into the Dungeon (free/pay what you want). This game consists of six pages which is mostly charts. This game is like Four Against Darkness on speed. It used two six-sided dice. This game does not generate a map, but I wanted to. So, I combined it with Castle Oldskull – Oldskull Dungeon Generator. Both of these items are available at DriveThruRPG. These items can be for a Game Master and several players, or for solo play. I used four characters. In the first room my adventuring party encountered a medusa with one snake hair which was doing ranged damage. Things started getting nasty when they entered the fourth room. The floor was a false floor and they fell down to the second level taking falling damage. And to greet them were two vampires. These monsters were killed as well and the party was relieved to find stairs leading back to the first level. The eighth room was an alchemy lab, but the party was not able to recruit the wizard. The ninth room was a vampire and four of his thralls. When the vampire was killed, the thralls seemed confused. The dwarf fighter started waving his holy relic around and the thralls made a run for it. There could have been some nice treasure down there, but the dice did not behave – it was just gold and gems. So, all four escaped and made it and are now second level characters. Give both a try!