We have a First Night; I've gone a few times and even volunteered, but I've stopped because it's always the same.
The town gets pretty rowdy on Halloween, and a lot of people run around downtown (where all the clubs are) in odd costumes, sometimes none at all. I've been there :-).
We've got several art and wine festivals which I consider lame and don't go to anymore. Mainly an excuse to sell stuff. There is a big artist's Open Studio tour however, countywide, with about 200 studios open, and I like to go around that and even buy stuff from time to time.
Things I don't participate in: the local "Wharf to Wharf" run in which several thousand people run about eight miles along the waterfront, the various surfing competitions and beach volleyball tourneys (I don't do either).
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