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In the 1880, Chippewa Co, George is living next to William and Jane Penfold. Jane is his half-sister, Eliza Jane, dau. of Robert and Isabella (CUNNINGHAM) DOUSLIN. Isabella, widowed, is living on the other side of the Penfold family.
I've not yet determined the exact year George was in Cheboygan Co, but his dau. Judith Anne m. Peter MORWAY, of Cheboygan, in April 1887. However, this marriage took place in St. Ignace and Judith is said to be of Rosedale, so the family was likely still in Chippewa Co then. How'd she meet MORWAY?? The first Cheboygan County event I have is the marriage of George's son William to Ida RICHARDS on 17 Sept 1891. The Richards family appears in Cheboygan on the 1880 census, so the Montgomery family had to have been there long enough for William and Ida to meet before 1891. My guess - the Montgomerys were in Cheboygan by 1890.
PENFOLD is such an unusual name - I feel there must be a connection.