Originally Posted by
smidsy
Just to throw another thought out there, several of you have pointed out the issue of weight distribution - the second trailer taking weight off the tow bar.
If you're going to do this you're already certifiably crazy so why not go the hole hog and make a dolly.
An axle, a bit of framework, a light connection and a tow ball mounted over the axle so the weight of the second trailer is transmitted straight down through the axle & wheels of the dolly - you could make it a standard tow ball or a fifth wheel and you could even go nuts and build a four wheel dolly.
Even if you couldn't get it legal it's almost worth doing just for the fun of it.