I can't speak for Canada, but I'm told a large proportion of it's legal system is based on the British legal system which I am familiar with.
In the UK you wouldn't be able to follow the plan you outlined because the brewing and selling licenses are independent of eachother and breweries who wish to sell commercially have to be centrally registered with the tax authorities. This is down to the tax arrangements on alcohol, which is subject to normal VAT (currently 20%) at the point of sale, but also subject to "beer duty" at the point of production. Beer duty has to be paid by the brewery and is ususally paid at the point the beer physically leaves the premesis. The beer duty rate depends on the ABV strength of the beer produced, but a typical pint of 5% beer would attract beer duty of 55 pence (about 86 cents).
In practice there's no short-cuts or legal loopholes for brewpubs. A pub wanting to brew and sell it's own beer (and there are quite a few who do...) would need to hold both a brewing license and a sale license - and tax would be collected on both the act of brewing and also at the point of sale. You'll probably find if you dig a bit deeper that the Canadian laws will be similar - i.e. for tax purposes the taxman would consider the brewery and retail activities of a brewpub to be distinct, taxable activites and wouldn't allow you to argue that because the activities are taking place within one building or location that nothing had been "transported". They may even require you to register the pub and the brewery as seperate legal entities and require that you keep seperate accounts for each which clearly show the transfer of beer from one entity to the other, and the collection of any required taxes as part of the transfer.
Don't take my word for it though - as I said, I'm familiar with the UK law, not Canadian law. Having said that, I'd be very surprised if the Canadian authorities had a noticably different set of rules which allowed the brewing and sale of beer without the payment of some sort of tax on production - for the simple reason that I know of no government in the world that would allow potential tax revenue to escape their grasp that easily.
