One of the charms and frustrations of the Maine coast is how two places that are short distances from each other, at least as the crow flies, can easily be a 30-to-50-mile drive. That makes it no small adventure to drive out for oysters and lobster rolls in Portland’s Old Port, but it also means that staying on Westport Island can feel like you’ve flown to Scandinavia. The other quirky thing about Maine is how it packs rural red-state folks so tightly in with blue-state retirees and summer residents—in Wiscasset, a black cutout of a cow, nailed to a farm fence and painted with white letters spelling T-R-U-M-P, marked the turnoff to the island, where we stayed in an 18th century inn on a fjord-like inlet.