I don't think you'll need any special license, or at least I never did. Check with your insurance company just to be safe about coverage. They might want to know some dates but probably not. At the border they aren't the DOT enforcing highway laws. What they are after is to make sure nothing stolen and no people of bad reputation gets in their country. They are also concerned about you as a US citizen doing commercial business in Canada if you're driving A pickup pulling a trailer. I don't know what they will say about a toolbox full of tools or the chains or straps in the back of your pickup. It might just be considered luggage. We had to pay a duty on the tools in the tool trailer when we came through with the combines but we were commercial, so that might make a difference.
The boss and I went across into Canada driving a pickup with the farm name on it one March day ten years ago. We were going into Canada just for a social visit with a customer, but they saw the farm name on the pickup and pretty soon we were in the back room being questioned. He was coming at us from all kinds of angles but we were polite and friendly and stood our grounds that we were just there for a social visit and that there was nothing commercial about it. They finally let us through without ever glancing in the pickup. Just be sure you have the name of the person you are dealing with in Canada and where he lives. They'll want to know when you plan to be leaving Canada so it's good to have all that information in your head before you hit the crossing. Yes, you will need a passport. Wish I could go with you. Haven't been up there for five years or so. Jim
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