K of G - I think you're Sunday School group may have it backwards. The lands of Kentucky were settled by many people of English descent, (my own family is full of English stock by way of Kentucky) so if you go back in the family trees you'll find many English names. Bilbo would be an unusual name though; mostly folk were going for the Biblical names by the late 19th century, but it may have been an old family name.
As for "pipe-weed": by the 1500 tobacco from the Americas had been introduced to Europe, so the first European settlers in America may have already taken up the habit before they came to the New World. (I'm not sure if it was cultivated in England, which is too far to the North) but they were definitely smoking it.
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