I have only attended on con in my entire life, which would be GaryCon. It's a con that started small and got big. And much like the con itself, my approach to attending it started small and got big. In fact, I think I may have overstepped my endurance in the last couple of years. But that's a different subject for a different time. However, after attending GaryCons I-IV, I can't believe that I waited until my mid-to-late thirties to attend a convention.
Tabletop gaming is a social hobby. Usually the groups one runs in are pretty small. You may get half a dozen at the table and a few more in your local game store. With the hobby moving from the tabletop to the laptop, we've been getting more isolated from our fellow gamers. as my friend the Geekpreacher would say, "Gamers are not socially awkward, they are awkwardly social." Like a lot of people we need human (or demi-human) contact every once in a while to keep us sane. The nice thing about conventions is that they provide a temporary oasis for gamers. For a weekend, we get to be around a rather large group of people that aren't going to look down at us as freaks or nerds. It's pretty awesome to know that in a small hotel in Wisconsin I have managed to meet people from around the world who I have something in common with.
Next year I will likely spend less time gaming and more time socializing. But the important thing is that I have a con to attend. No matter what your hobby may be, it's nice to get out to someplace and feel like your little hobby isn't so small after all. And more importantly, it's nice to know that there is someplace out there where you belong.