Throw me in as a vote for the Pine Tree Flag.
The pine is the Yankee symbol of choice, and it is centralized in the middle of the flag, a pleasing symbol equivalent to the Japanese or Swiss flags. The two blue bands (I'd wish for green for simplicity's sake, but that doesn't change blue still looks pretty good in and of itself) are a nice decorative framing device. The explained symbolism works best with the watery frames enveloping the snowy land and the pine that rises above it all. This is a flag passing with flying colors in both directness and simplicity, the kind all sorts of designers would kill for.
By now New England is its own country, has its own traditions, and even the Anglo portion that's nominally closest to Britain itself has its own unique history and dialect. This flag represents all that without being a dull tricolor nor cribbing the Stars and Stripes.