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Winchester is just NW of Boston. I grew up NE of Winchester, about 25 miles away. We don't have hills like these in eastern Mass -- either as barren or tall. There are even small foothills in this image, much more like western ranges (where I've also lived).
While it's been rather dry in the East, it surely hasn't been so arid that it's desert-like a mere hour's drive northwest of Boston! The barns (and most of the other outbuildings) at Wright-Locke are painted white, and none have a gambrel roof like the photo above. The roofs & most of the doors are gray, & there's only a single cupola on the roof. In the 40+ years that I lived in the Northeast, I never saw mountains like these. But I have seen quite a few out West that appear much more like those above. Sorry Carolyn, but I feel I need to agree with the others. No matter, I still enjoyed the puzzle!
I was born in the Berkshires and I too am surprised by the bare mountains.
This is the Wright-Locke Farm Conservancy in Winchester, MA, Look it up Mr. Geographer!
I doubt very much that this picture is from Massachusetts. It looks more like the west or midwest - too dry, mountains too dry and stony instead of green and lush. Even the buildings look more western than eastern.