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I know I was reading something about a rare Halifax cancel somewhere in early Canada but can't jar my memory.
I am not sure which Halifax cancel you are mentioning.
There are Morris St. and Gottingen St. post office Street CDS Cancels from around the turn of the century, they did occur on the Tercentenary issue stamps sometimes.
The Morris St cancels were mostly socked on the nose, as a retired sea captain was the post master and demanded accuracy, but the Gottingen St ones were usually off center and only partially on the stamp. (I know a fellow that has a special collection of just the street cancels from Halifax, a calendar collection too, by gum.)
The Squared Circle cancels and precursors from Halifax are not too rare really compared to others.
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Maybe I have a rare Winnipeg though
That is a beautiful socked on the nose Squared cirle from Winnipeg.
There are 4 types of Winnipeg Squared Circle type II (thick bars) cancels, only one is really rare, and I don't have the book that tells you how to tell them apart. (Squared Circle Postmarks of Canada)
The Airmail slogan (part of a machine cancel) is not rare but nice. The 'Ste. Rosalie P.Q.' Split Ring Cancel (there are also other names for this type of cancel, Split Circle, Broken Circle, etc) is a nice name, should be in a song or something. I do not know about these types too much nor have a book. Some collectors specialize in them. It is nice though. I have seen some split rings but not that one so there is hope yet!