Portland DOES have a whole lotta cyclists. Vancouver, BC, has lots of commuters, but I noticed when I first visited Portland last December, and again just recently, that the Portland ones seem more numerous, and more dedicated, too. And they have much more cool gear (like YELLOW fenders).
I think the helmetlessness (!) you observe may be similar to that seen in many European commuter cycling meccas like Amsterdam. Just like driving, for North Americans, is not perceived as something that's dangerous (despite enormous evidence to the contrary!!), cycling also feels less dangerous when there's a mass of people practicing it, when it's practiced daily, and when there are some proper infrastructures to practice it.
Whether or not it is true that it's safer is a complex statistical matter. My own take has been to wear a helmet for commuting and road riding here in my corner of the continent. However if I was riding a Dutch bike in the middle of Amsterdam, I'm not sure what I'd end up doing. Our social mind plays tricks on us...
On the thread topic: I have just started commuting in my new area so it's hard for me to make an enlightened observation, but my father-in-law who's been road riding (not for commuting) for years on a few of the local bike routes says he's never seen so many cyclists around 4 p.m. on that route...




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