In the past, I've collected a select set of comic books, but have never been to a 'comic con'. That said, I've never been to one of the big sports cards shows either. I like events, but as I've mentioned earlier I'm no fan of crowds.
As far as the interesting costumes, it's no different than when you stumble upon a SCA gathering in the middle of nowhere.
When it gets down to it everybody wears a costume every day in their life.
There's something for everyone out there, and for each of those things there's someone who thinks it's just a bit weird. Keeps life interesting
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That said, I found it real easy to get lost in beantown myself the first few hours I was there. The bonus being now I think I could find my way around without guidance on a future trip.