It might just be Shakewood, after all

Hard to tell for sure from the shingle colors you posted, but a medium gray to charcoal would be nice.

Just focusing on the roof in this photo, this gray would be perfect IMO.

That's amazing, I had this very thought this morning! Thank you! Thinking of painting the trim white and possibly investing in less "rustic" shutters down the road. I will certainly post b&a's!

Williamsburg Slate if those are your choices. Were it me I would look for something a little more gray than the slate, which usually ends up with blue, red andgray mix. Get the roofer to bring a couple bundles of your choices to the sute and lay them out on the roof if at all possible. You do not want to make decisions based on the shingle sample board alone, especially for such a prominent roof as yours.

Charcoal. Hard to say without seeing a picture of the current colors.

CertainTeed over GAF. CT Landmark PRO shingles. Grey tone would look nice.

This has been so wonderful! Thank you all so much for your input..I especially loved hearing about the very bold color combo on the fellow coastal New England Dutch. We're a few miles from the coast here in RI, and one fellow Dutch Colonial kit house on our street is cedar shake with bright yellow trim - it's oddly fantastic. Can't beat good bones!

I visited the roofer today and got a handful of sample boards, but you're right - impossible to decide based on those since the whole optical illusion is lost without distance and scale.

I do think the Williamsburg Slate shade is our best crossover option..it won't be offensive with the existing colors on the house (tough to see in first photo, but trim is denim blue), and it'll look even better once we change them.

I'll be back before too long with the b&a's!