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The specific area of the North Shore you're referring to is Cape Ann, which has a distinctive, old puritan Massachusetts feel to it. Reserved, lily-white, educated, affluent, maybe a little snobby. I have lived there and I am familiar with the Gordon crowd.
Hamilton/Wenham are very rural and upscale, Manchester is also very upscale Essex and Ipswich are more affordable, lots of farmland.
Beverly and Gloucester are the only diverse neighborhoods on Cape Ann - afforable (relatively) and urban. Salem is too and close enough to Gordon.
Great beaches - Singing, Crane, Long, Wingaersheek ... awesome place to live in the summer.
You'll definitely be getting a potent dose of pure Massachusetts up there.
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