Whenever I pack for a trip, my first step is to pick a color palette. I know it probably seems strange, but doing this allows me to take less and to mix and match many different pieces dependent upon what we're doing and how the weather treats. No shock I'm going for neutrals here, but I'm adding a little coastal blue to honor the occasion.
I once got caught in Boston in monsoon-type rain and every since then, I won't travel without rainboots. So I'll throw them into the car in case I need the, and luckily, there's a great pair of Hunters included in the Nordstrom Anniversary Sale if you're in the business for a new pair. I also love the packable ones that come with their own carrying bag.
Sneakers are a must and I've recently added quite a few pairs to my wardrobe. I snagged these at the #nsale (the black and the white) and they might be the most comfortable sneakers I have ever owned.
What am I forgetting? I know it gets cold at night so I have quite a few layers packed... I should probably add lots of socks too, just to be sure.