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1.
A territory or piece of land that trades hands between ownership so much, everyone stops caring who owns it.

In the board game Risk, it's when two or more people fight over one territory every single fucking turn. It's a large waste of time, unless that territory is something like the one thing you need to own the continent.
Person: The Louisana Territory was Gray Land before it was bought by the USA. Like six countries owned it before we did.

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Red Player: I want Brazil!

Blue Player: No, I want Brazil!

Green Player: I want something that isn't Gray Land.
by iamthelaw_633 December 27, 2010
 
2.
1) A grayland is when one drunkenly navigates their way through the entire length of their road or street, entirely nude, before pausing briefly to defocate. A grayland is often performed under the cover of darkness and after copious amounts of alcohol have been consumed.
2) The one and only Gray.
Hahaha, Dave just ran out his house nude and pooped on the pavement

What a classic grayland
by Xou June 12, 2008