Let the site and local environment influence the color selection.

If you're using real cedar shingles, did you ever consider a shingle roof? I have a house in that area, and we have both wood siding and roof. It's a fairly common combination for homes out on the East End of LI. The wood weathers to a silver gray and blends in with the environment.

Certainteed can give you a list of homes in your area with Landmark roofs. Take a look.

My roofing contractor brought full sized shingles for me to choose from. I could stand them up or lay flat next to the brick and look at different times of the day. It was immediately apparent the two greys I was considering were wrong (Cobblestone and Georgetown) and the Weathered Wood was the right choice for me.