Fair question. The only guidance I was able to find on TSA.gov was that "fruits" are ok to carry on, but they give, you know, a plum as an example. And I don't think I'm going to be able to point to my iphone in security, show them the language and say, "see, it says fruit is ok." And I suppose a pumpkin is a vegetable anyway.

As for the carryon size requirments: Well, first of all, we know those aren't enforced. Second, and more importantly, there is a lenght, width, and height requirement, but I've never seen any scientific proof for exactly how to apply those to a pumpkin. Meaning is the longest axis the lenght or the height? is a really "tall" pumpkin really tall, or is just being measured on the wrong axis. I'm not being funny--I'm dead serious. Height, width and length is just another way of saying it has three distinctly measurable sides, and each can be a certain length. Put another way, a 14 inch "tall" pumpkin which is 9 inches "wide" when placed on its side is 9 inches tall and 14 inches in length.