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I noticed that the 1855 stampless cover, and the 1976 cover are sent to the same person
Gilles, I didn't even notice the names on the different envelopes. The initial on the stampless cover does look like a J, but I think it's a T. In fact, on the notice inside, it's written like a Y.
Unfortunately Ridgefield Rd in in north central Toronto, while Etobicoke is a part of Toronto's west end.
Wouldn't have it been great to be in the same area. Quite a coincidence none the less. Maybe one Montgomery is a descendant of the other?