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Aha! Plymouth Colony was settled by the Pilgrims from the Mayflower, and a middling shade is grey. So #1 could be either GREY PILGRIM, or MITHRANDIR if you prefer the Sindarin.
For #3, a long trek may be a march. There's only a few things starting with March, and one of them is the surname MARCHBUCK, which ends with the first American currency unit available as a note.
Marchbuck is given by Tolkien as a more accurate translation of Brandagamba, the surname he translated Brandybuck in the books. I don't know what the Washington-Jefferson connection is, though.
hS
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