Way back in the blog scene of 2008, there was quite a bit of discussion about what is the best way to present a dungeon. Old adventure modules from the 70s were examined for inspiration and then new ideas were introduced to attempt to convey as much information about a dungeon as quickly as possible without overwhelming the reader. Out of the discussion, the "One Page Dungeon" format evolved.

A noted writer on the Critical Hits website (ChattyDM) picked up on the "One Page" discussions and spearheaded the idea of running a contest to get the community involved. Enlisting some of the principal players of the evolution of the format (Sham and ChgoWz) , the first contest was organized in 2009

For the next 4 years, one of the judges from the original 2009 contest (Alex Schroeder) diligently took up the mantle of coordinating the contest. Thanks to his dedication the contest was held for the next 4 years; 2010, 2011, 2012, 2013. There have been over 350 entries combined after five years of contests, covering a versatile range of playstyles, settings and genres. Best of all, every entry is licensed under the Creative Common Attribution-Share Alike 3.0 license for all to use.

Timeline: 
How do you go about designing your MegaDungeon odd74 post by dwayanu, December 21, 2008 
The Dismal Depths by Shame (aka Dave Bowman), December 29, 2008 
One Page Dungeon Level Templates by Chgowiz (aka Michael Shorten) 
Dungeon Jazz by Amityville Mike (aka Michael Curtis), January 2, 2009 
Building the Font of Sorrows by ChattyDM (aka Philippe-Antoine Menard), March 17, 2009 
New Grand Contest: The One-Page Dungeon! by ChattyDM (aka Philippe-Antoine Menard), April 14, 2009 

So, what about the future?
Alex Schroeder passed the torch to Random Wizard for the 2014 contest. 
Random Wizard organized the contest for 2014, 2015, and 2016. After the completion of the 2016 contest, Shattered Pike Studio produced the 2016 compendium, and became the organizer.

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Organizers Through the Years

• Alex Schroeder organized the first 5 years of the Dungeon contest

• The torch was passed to Random Wizard who organized the contest for 2014, 2015, and 2016.

• After the completion of the 2016 contest, Shattered Pike Studio produced the 2016 compendium and became the organizer through the 2020 dungeon contest.

• Beginning in 2021, Todd from Spiel Knights became the dungeon contest organizer.