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CASTLE OLDSKULL - Oldskull Adventure Generator


A Platinum Medal DriveThruRPG Best Seller


The world’s ultimate adventure creation tool. Infinite possibilities await you in dungeons, the wilderness, the seas, skies, netherworld, and the planes of existence. Whither are you bound?


Years in the making and now revised for the future, Wonderland Imprints supplement OLDSKULL ADVENTURE GENERATOR (GWG2) is the “Rosetta Stone” of the Castle Oldskull system, the one master system which binds all of the present and future supplements of the Castle Oldskull OSR gaming universe together into a massive unified imagination engine. Harness the power of over 30,000 data elements to create dungeons, villains, quests, and more. Your worlds of adventure will never be the same! Using this 300+ page supplement, you can create millions of unique adventures for your players. There are so many options, that in a lifetime of play no two adventures you create will ever be the same.

I believe (but would be happy to be proven wrong) that this is the most ambitious and extensive adventure creation tool available on the market. When combined with the CLASSIC DUNGEON DESIGN GUIDE series, you will have all the tools needed to design an entire fantasy realm that fits within a larger world of your own creation. Using this volume, you can create an entire campaign of multiple adventures, entailing wilderness journeys, dungeons, monster lairs, traps, tricks, treasure, and unforgettable tales. And when coupled with the GAME WORLD GENERATOR, you can create your own entire world of endless adventure and allow the Players Characters to journey anywhere. And while you both refine and refuse suggestions rendered by the random generators, you will be creating new realms of wonder — unique to your personal vision — every step of the way. Do you need a new island, temple, tomb, forest, swamp, mountain range, netherworld, or sea? This book will show you how to build them all, each uniquely detailed with their own locales and opportunities for play.

Another old school gaming experience from Kent David Kelly and Wonderland Imprints, Only the Finest Works of Fantasy. (Over 350 pages, 109,000+ words.)


To view the entire library of available titles for Castle Oldskull, Hawk & Moor, Old School Essentials compatible supplements, and more, please visit Kent David Kelly's Wonderland Imprints publisher page.

The Wonderland Imprints Swords & Sorcery Library


Supplement Title

Primary Game Topics


The Classic Dungeon Design Guide I

Dungeons / Lore / Random Tables


The Classic Dungeon Design Guide II

Dungeons / Lore / Random Tables


The Classic Dungeon Design Guide III

Dungeons / Lore / Random Tables


Oldskull Dungeon Generator

Dungeons / Solo Gaming Tools


The Book of Dungeon Traps

Dungeons / Random Tables


Oldskull Dungeon Tools

Generators / Solo Gaming Tools


Game World Generator – Deluxe Edition

Game World / Random Tables


Oldskull Adventure Generator

Game World / Random Tables


Chaotic Descriptor Table

Generators / Random Tables


Dungeon Delver Enhancer

Characters / Lore / Random Tables


Oldskull Warriors

Characters / Classes / Lore


Oldskull Knights

Characters / Classes / Lore


Oldskull Anti-Paladins

Characters / Classes / Lore


Oldskull Plague Doctors

Characters / Classes / Lore


Oldskull Gonneslingers

Characters / Classes / Lore



Characters / Races


Oldskull Half-Ogres

Characters / Races


Oldskull D100 NPC Generator

Characters / Generators


Character Tables

Gameplay / Tabletop Reference


Combat Tables

Gameplay / Tabletop Reference


Dungeon Monsters & Treasures Level 1

Monsters / Treasure


Oldskull Dungeon Encounters

Lore / Monsters / Treasure


Oldskull Dungeon Bestiary

Monsters / Random Tables


Oldskull Dragons

Monsters / Treasure


Oldskull Trolls

Lore / Monsters / Races


Oldskull Monster Generator

Generators / Lore / Monsters


Oldskull Treasure Trove

Random Tables / Treasure


The Oldskull Deck of Strangest Things

Lore / Random Tables / Treasure


City State Encounters

Random Tables / Urban Adventures


The Order of the Scarlet Tabard

Characters / Lore / Random Tables


Captains of the Scarlet Tabard

Characters / Lore


Oldskull Tyrrhenia Map Pack

Game World / Lore / Realm Maps


333 Realms of Entropy

Game World / Lore / Monsters


1,000 Rooms of Chaos

Dungeons / Solo Gaming Tools


1,000 Rooms of Chaos II

Dungeons / Solo Gaming Tools


The Pegana Mythos

Characters / Game World / Lore


The Oldskull Necronomicon

Characters / Game World / Lore


Lords of Oldskull: Krampus

Classes / Lore / Monsters


Character Creation

Basic / Expert (B/X) Characters


1977 Bestiary

Basic / Expert (B/X) Monsters


Adventurer’s Arsenal

Basic / Expert (B/X) Equipment


Turn Tracker

Basic / Expert (B/X) Gameplay


Oldskull Grid War

Basic / Expert (B/X) Gameplay


Hawk & Moor Book I

TSR / Gary Gygax History 1973


Hawk & Moor Book II

TSR / Gary Gygax History 1974


Hawk & Moor Book III

TSR / Gary Gygax History 1975


Hawk & Moor Book IV

TSR / Gary Gygax History 1976


Hawk & Moor Book V

TSR / Gary Gygax History 1977


The Steam Tunnel Incident

TSR History / 1980s


(And more can be found at the Wonderland Imprints publisher page.)

Don't know where to begin?

Each of the Wonderland Imprints series has an acclaimed first introductory volume. You can start there, and then journey further as you choose.

Series include the Black Label Editions (unillustrated tabletop volumes), Castle Oldskull (old school RPG supplements), The Classic Dungeon Design Guides (system neutral dungeon crafting), Hawk & Moor (Dungeons & Dragons history), Old School Essentials (supplements for Gavin Norman's B/X game), Oldskull Innovations (unique experimental products), and the Oldskull Library (classic weird fiction), as well as many Free Supplement Releases.

 Customers Who Bought this Title also Purchased
Reviews (2)
Discussions (9)
Customer avatar
Lesley N July 21, 2022 9:00 pm UTC
My first purchase made this purchase easy.

A very good product Kent. Another option in hardcover if I could get it. Easily worth it.
Your titles easily exceed what is commonly offered out there for this sort of item. And a fraction of what they ask for theirs.
Customer avatar
Tom G August 28, 2020 9:58 pm UTC
Just got this today. Printed the worksheets and started filling them up with results from the random tables. I am impressed with the quantity of ideas presented and hope to make use of this. Am I missing the link, or are there no tables for Benefactor Race?
Customer avatar
Tom G August 28, 2020 10:04 pm UTC
on another note, I just rolled 977 on the Reward does not exist. 976= treasure, 978 we come to an agreement. so...I shall bump up by one, but you might want to make some fixes as the errors are found.
Customer avatar
Gabriel D July 01, 2020 4:32 pm UTC
Hey, Mr. Kelly. Your products are some of my favorites: my overwhelming go-tos for inspiration and game design. Consequently, I “reacquired” the Dungeon Design Guide as soon as you offered it in print. Ever since, I’ve been eagerly awaiting print options for your other “core” titles, as well.

In my long view, I’m looking at Dungeon Design Guide III in print (it’s so useful!), but I will happily buy the Adventure and Game World Generators, too, during that journey. Please take this comment as encouragement to continue, whenever possible, with offering print versions of these titles.
Customer avatar
Ian R March 22, 2020 6:32 pm UTC
There seems to be quite a few errors on some of the tables. A lot of words like "Hrt Ib" or "Axnwty". Then there are words that seem like real words, but I could find no definitions for like, "Tepidarium", "Apodyterium", or "Kneipe". And those are examples from just one table. Most of the larger tables are like this. Is this a formatting error or just bad editing? Overall it's a good product and gives some order and instruction to something that a lot of people have trouble with, but there are so many errors and redundant entries that most of the d1000 tables "only" have about 300 usable entries.
Customer avatar
Gary A May 28, 2019 1:47 am UTC
Small error: Page 334, table GWG2-68, entry 37 to 40 is just a backtick ("`"). What should it actually be?
Customer avatar
Kent K June 15, 2019 12:05 am UTC
Hi Gary, sorry just saw this. The correct entry is 37-40 Forested Mountains, which corresponds with the definition Forested Mountains: Mountains which are covered with significant forest (up to treeline). This book is being reformatted currently, similar to what I just completed for The Classic Dungeon Design Guide, but due to length and complexity it's going to take some time. :)
Customer avatar
Peter S May 06, 2018 4:33 pm UTC
Probably the best book Ive ever gotten off of DTRPG. 5 stars.
Customer avatar
Brian H October 20, 2017 4:07 pm UTC
I had problems downloading the print edition of the file:

Try Again

Customer avatar
Louis M July 10, 2017 11:27 am UTC
This is pretty good. I love stuff like this. My complaint is that the font, spacing, and scores of odd public-domain pictures make it a chore to wade through. It doesn't seem to be formatted for ease of reading/use in any way. (Printing it out would be a huge paper and ink waste as well.)
Customer avatar
Allen H June 23, 2017 12:29 pm UTC
I haven't consumed enough to write a formal review (lots of tables to browse through), but this seems well worth the money. Anyone interested in sand box gaming (and I've seen many a question regarding such over the years) is well advised in picking this up. No wasted pages. Lots of d1000 (yes, 3 zeroes) tables for creating random adventures and anything related to them. Think of those Adventure/Plot/Screenplay generators you've seen over the years, then expand them by 10x, or more.
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This title was added to our catalog on June 05, 2017.