Is it legal in Ontario to tow two trailers behind a pickup truck?
Short answer, yes.
There are weight and length limits. I believe they're 23 metres and 4,600 kg.
Here's the part most people get confused on...
You cannot tow more than one trailer behind non-commercial vehicles.
Pickup trucks, regardless if they're for personal use, are considered "commercial vehicles" for highway traffic purposes. An easy way to confirm whether or not your vehicle is considered a commercial vehicle are through your plates. You'll likely have a set of black lettered plates instead of the blue. If so, you have a "commercial" vehicle.
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