I don't know the legalities but I see some pick up trucks pulling two trailers on the interstate from time to time here in Tennessee so I assume it's OK. I have a two wheel sulky that I pull behind my goose neck trailer sometimes and I have never had a problem but I have never gone over 50 miles from home or been on the interstate much. I have it on a good hitch, it has lights and safety chains but I am not sure about the two trailers thing being kosher.
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