Weather, and What to Bring
Mountain/Valley weather in the sholder seasons of May/June and Sept/Oct is about as variable as it gets. You could potentially see anything: sunny, warm days topping 80, brisk, clear days in the 50's, afternoon hail and thunderstorms, and even high country snow. A "typical" ride might start in the morning at 45F, progress to a higher altitude with a chilling downhill, and finish in the valley at 80F, only to encounter colder wind or rain on the way home at 2 PM. So, bring it all!
I will have (for myself), leg warmers, arm warmers, a thin jacket, and thicker "podium" style riding jacket, a beanie, toe warmers, full finger (thin) gloves, long and short-sleeved shirts, and poly-pro under garmetn, like UnderArmour. If it's so cold I'd want wind pants, I probably won't ride. Photo sensitive sunglasses are very helpful for the changing sky.
I don't have a lot of extra water bottles, so you'll need to bring what you need.
For non-workout clothes, even if you go to a ritzy restaurant, jeans and a casual shirt work just fine.
We've got a hot tub, so even if you don't plan to swim, you might want to bring a swim suit anyway.
Comments
I'm bringing my cold weather gear (stuff like Al has listed above), short and long sleeve jerseys, running stuff, no swimming stuff at all.
Jeans and t-shirts are as fancy as I'll be bringing, clothes-wise.
Do we know what the sleeping situation is yet? Do I need to stuff a sleeping bag in my bike box?