I adore good picture books, so finding good Canadian ones is like a treature hunt for me. We just read a book called Duncan's Way by Ian Wallace that touches on Newfoundland, after the cod stocks began to disappear. It's a beautifully illustrated story book. A Fiddle for Angus by Budge Wilson is another lovely picture book; it is set in Cape Breton and encompasses the music and family culture there. I was very excited to find The Red Sash by Jean E Pendziwol; it is set at Fort William during Rendevous and gives a great (and accurate) picture of the Fur Trade through the eyes of a young Metis boy. Baseball Bats for Christmas by Michael Kusugak gives a unique picture of the arctic region of Canada. Tiger's New Cowboy Boots by Irene Marck gives a great picture of a cattle drive in Alberta. If Your Not from the Prairie by David Bouchard is also an interesting book--especially the beautiful illustrations. We've also found Barbara Greenwood's books helpful (we read Gold Rush Fever last year and enjoyed it). My all time favourite spine for younger elementary is My First History of Canada by Donalda Dickie.
For older kids it is harder. Maxine Trottier's The Circle of Silver Chronicles trilogy is good and so is Jeremy's War 1812 by John Ibbitson. I also like Madeleine Takes Command by Ethel C. Brill.
Rilla of Ingleside by Lucy Maud Montgomery is a fantastic Canadian picture of WWI. Evangeline by by Henry Wadsworth Longfellow is also lovely when studying the Acadians.
The Spirit of Canada anthology has also been wildly popular at our house.
Hope this helps get you going!