Hands down, the most popular online riddle, and perhaps the inspiration for most others is "Notpron." http://www.deathball.net/notpron/. Notpron claims to be "The Hardest Riddle Available on the Internet!" And it may, in fact, be true. There are 140 levels and they start becoming very challenging after about twenty. This riddle will stump you, infuriate you and mock your intellectual weakness, but it might just be the most fun you'll ever have on the internet. It incorporates all aspects of its pages, including the URL, hidden text and images, use of other common software to solve problems, and much more. NotPron makes it extremely to difficult to "NotCheat."
Clever Waste of Time: http://www.cleverwasteoftime.com/ (as perhaps they should all be called!) boasts one thousand total levels with six "trail levels" and five "side quests." This internet riddle uses the tools already available on your computer, as well as a lot of researching on the internet. CwoT promises to teach you the skills you need for riddling, so prior experience is not necessary (or required). Perhaps a good place to start if you are a novice riddler.
Web Riddler: http://webriddler.9.forumer.com/ Is much different from other internet riddles in that instead of being browser based, it is forum based. This riddle looks interesting for those more involved in text and language. It does not have the aesthetics the others have, as most of the clues and solutions are in black and white, the written word.
Dschingis Riddle: http://home.arcor.de/dschingisriddle2/ claims to be a browser-based riddle, moving from screen to screen and obtaining hints on each screen. To even start playing, your first riddle is to find a username and password. So basically, you have to find a key in the mud before you can even open the door. This riddle appears based in Germany with a sprinkling of German words, but they do offer hints along the way.
Jaor:http://www.jaor.net/ Jaor's index page looks like a 50's postcard and offers a forum where users can exchange ideas, hints, etc. Part one starts right away with an image, and with most of these riddles at the beginning what is necessary is a click on the page or a change of the URL. There are three parts in all, and a Hall of Fame showcase all of those that made it through the riddle alive.
Badpron:http://maskims.free.fr/badpron/ Badpron starts with a sign on a road stating "You are Entering Nowhere" - appropriate for these types of games. Who knew Nowhere could be so much fun! BadPron is similar to NotPron and is directly inspired by it, not meant to be harder or easier. They offer hints and ideas, and even a contact email in case you get really, really lost.
Wayfarer's Riddle: http://homepage.ntlworld.com/mwturton/wayfarersriddle/ is a nod to NotPron, so more than likely very similar to it. There are 200 levels, plus 17 side levels waiting to be completed. There are also Puzzle Levels and Mysterious Levels that deal with 18th century England. For the first eight levels, they offer hints to those who find themselves stuck.
Python Challenge: http://www.pythonchallenge.com/ claims to be the "first programming riddle on the net" with 33 different levels to be solved. If you are not a computer programmer with Python programming language background, I would not attempt this puzzle! Still, it has the same look and feel as other internet riddles, and for those in the know, proves to be lots of fun.
Historiddle:http://historiddle.50webs.com/ Thought learning history the hard way was by sitting in a lecture hall listening to the professor drone on and on? Wrong. Try playing Historiddle. You do not have to be a history buff to do well on this site, just able to examine and interpret the clues on the page. It uses asterisks to give you an idea on how difficult the page is (one to three, three being the most difficult). This riddle requires you to do some googling and research, and who knows! You might just learn a thing or two along the way.
Nicky's Riddle:http://nickysriddle.tripod.com/nickysriddle/index.htm Nicky's Riddle is based, again, on notpron, with forums available for help, a Hall of Fame, and hints to get you moving along. A few things to remember when playing these types of riddles are: look for hints in the source code (which can be found by clicking View then Source), hints in the actual URL (website address), and in the name of the page. You will, on occasion, find an Easter Egg designed to either make you feel poorly for your lack of skill, or to build up your riddle ego. In Nicky's case, in the source code on the first page of the riddle you'll find "Looking at the source code this early on is sooo useless!"
Enjoy your newfound form of entertainment, just don't let the boss catch you or you could be riddling full time!
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Published by Tricia Urlaub
Tricia Urlaub lives in Upstate New York with her three sons. She has published fiction and non-fiction both online and in print magazines. She is Editor of the speculative fiction online magazine, Tales from... View profile
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