I understand from a friend whose family was the first to settle on Kenniston Island, that they did so in the 1880's. They were railroad employees and commuted to the island from Wolfeboro by rowboat. They rowed out all materials to build the cottages (still there) - imagine the effort? Once built, they would leave their families out on the island while they went to work for the week - no electricity, no boat, stuck until the hubby rowed out Friday night. Real pioneers - or nuts!
I would think that those are among the oldest island residences still in existence.
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