I re-read this after posting and thought to add a a few things. First is it currently registered in your name in USA but physically in Europe or are you riding it informally unregistered, or still registered to previous owner? If it is in your name then shipping it first to the US and riding it to Canada and following the importation process while costly should be fairly straightforward. You would need to first confirm that it qualifies for RIV or if it is exempt. Vehicles over 15 years old can be imported into Canada more easily as they are not subject to an inspection which from my understanding is governed nationally by transport canada. The issue, is registering them provincially and insuring them. If it is a known standard model there are ways of doing this fairly easily, and it is even possible to enquire provincially in advance as to what the process is and what documents you can use to show that it was built as a street legal vehicle and can then be registered. If it was originally registered in the US that should actually be quite simple.

If anyone following the thread has more details on exactly what the rules and limitations for leaving a foreign registered vehicle in EU indefinitely and possibly selling it to other non-EU nationals and re-registering it that would also be very helpful to know. My understanding is that often the vehicles are not officially entered into any system and not given a TIP, and that individual countries do have rules about how long a vehicle can remain in their country without being imported, but that seems mostly to be concerned with nationals from other EU member states keeping there vehicles indefinitely and either not officially becoming residents themselves or becoming residents but not formalizing the status of their vehicle. As it pertains to US or Canadian registered vehicles it is unclear to me. Firstly I understand that this hinges more on the legal status of the person rather than the vehicle, and if someone leaves europe but their vehicle remains then they are in a grey area, and if they sell the vehicle to another person and that person re-registers it in a foreign jurisdiction in their own name it becomes fuzzier still. On one hand I suppose that is a way in which a vehicle can be effectively imported without ever complying to road safety measures or paying the relevant taxes, and in another way it seems to me that the interests and concerns of member states vs. the governing body of EU may just leave a gap.