That looks great. Two questions; first, a bunch of maps show Aroostook as its own region, but I don't know if that makes sense, and second, based on maps I've seen, I'm considering making Vermont 3 regions, either adding a central region or splitting the northern region into NE and NW. Which makes more sense?
Splitting off Aroostook would make sense, it is a very distinctive region. I just figured that it's population is too small to justify giving it its own region, so I just conjoined it into a "Northwoods" region.
Personally I think a two-region Vermot makes the most sense, but if you're going to split it I'd say go for NE/NW
I think Vermont is best off split North and south along the Green Mountains.
View attachment 578078
this is my rough idea for Upper New England. I have no objection against the southern three states in New England - those are all pitch-perfect.
I think Downeast Maine is distinctive enough to warrant its own region. But if you're deadset on limiting it to three, I'd say cede Waldo and Knox to Downeast, cede Lincoln, Sagadahoc, and Androscoggin to Casco, and cede Kennebec to the Northwoods.
EDIT: Arguably Bangor/Penobscott County would fit in better with Downeast, though really this is only true for Bangor metro, and even then it's not a perfect fit - Bangor really is it's own animal. Plus, it adds the problem if making Aroostook a rather ugly jutting piece of the Northwoods, but it would be pure inanity to conjoin that to the Downeast.