This question is right up my main street! I have a massive collection of coins used in the American colonial/federal time period from Mexico to Canada and every thing in-between from coast to coast, starting from the 1500's.
The quickest way to get up to speed on Canada are these two books...
Amazon product ASIN 0919670865
and
Amazon product ASIN 0919909027
The first book goes into detail province by province decade by decade. The second book is Pierre Breton's MUST HAVE book on tokens used in the 19th century. Google "Breton Tokens" to get you started.
A quick answer to your VERY BIG question on Canada is this... The Canada we know did not exist in its present form until 1949 when Newfoundland finally joined. Before that "Canada" was a group of colonies, dominions and territories, each with their own governments, exchange rates, economies and separate coinage issues. The majority of Canada dates itself as a union to 1867.
The problem all the colonies had (America as well) was that the European monarchies had very little interest in the colonies beyond, prestige, resources, accumulation and WHAT CAN YOU DO FOR ME? But this ignores the fact that there was an increasing population, an increasing native economy and an increasing need for some form of exchange (money). So the European governments did very little to solve this need... in fact the European countries needed all the coins they could AT HOME for their own economies. Mexico and Spanish America supplied the WORLD need for coinage for about 350 years. These coins were the U.S. dollar of their day... they were used throughout the Americas, Australia, Asia etc. They were trusted to be pure of content and reliable of weight... plus the Spanish New World gold and silver mines were OVERFLOWING.
So as a result...literally... anything that could pass for a coin did so. One of the more famous examples of this is Montreal militia buttons.
When you consider U.S. history and the 13 colonies, consider too that there were OTHER British/American colonies at this same time that chose NOT to rebel. All of these colonies (the 13 too) were independent of each other and very jealous of their own decision making abilities. This is why the U.S. was set up as (now 50) "sovereign" states within an overarching union. Many had their own minted coins.
Of interest to me (and I guess to you also) is what was used on the LEFT coast. Remember, California was part of Mexico until 1848, the Russians had Alaska (and forts as far south as California) and parts of Oregon territory were disputed with the British. We (Washington State) were populated fairly late in the history of the lower 48. I remember that up until the 1980's we ALWAYS had Canadian coins in our pockets and NO ONE refused to take them.