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Utility Trailer = Canoe Trailer

Ok, now that I see the pic, I'd call that a "landscaper's trailer"! That changes everything!
2x6's will work, just remember to use some heavy duty angle brackets so your hardware goes through the grain, as end grain is very weak, and have your top rails overlap the uprights to keep water out of the end grain.
I'd also install some cargo rings on either side down low near the rails for straps. By mounting them low, you add the friction of your stake sides to the equation, so if your straps get wet and stretch, there is still front- to- back resistance. If you can get sufficient angle on your straps, blocks should not be necessary, but only time will tell.
Most of the wind will be from passing vehicles, as the trailer is in the car's slipstream, so side to side stability is crucial, a line from the bow back to the trailer should be enough to hold against sudden braking.
The biggest problem I see will be the bounce. Take the trailer for a ride down a bumpy dirt road and see how it handles. I suspect that It'll bounce all over the place with an unloaded suspension. There are two cures, the first is pricey, the second is hard on gas. You can take it to a trailer shop and have them pull a leaf (you need a pro to know which is the right one and to repack them) and downgrade the weight rating, or add sandbags to get it to "working load" (usually about 1/3 the tare weight), but it'll suck gas!
 
One other problem with trailers that needs to be addressed is the suspension. I have a commercially made canoe trailer. It has leaf springs, but the weight of two canoes is not really enough to compress the springs. On rough ground it tends to hop, which is hard on canoes. You need a soft suspension or maybe no suspension to avoid bouncing your boats down the road.
 
AlanP, you've gotten lots of advice on the mechanics and physics of building, modifying, extending, attaching, and towing the trailer.

I'm interested in the mental motivation. Why go through all these trailer mechanics and physics to transport one 29 lb. canoe? Why not just cartop it? I don't care, of course, especially if people like to tinker with tools and projects, but I am sincerely curious why you seem to be rejecting what seems to be the simplest transport solution.
 
Glen... I totally agree with your viewpoint. I have a 5x8 trailer, and it would shake the crap out of any boat I have....even a poly kayak. My trailer is a mid-weight capacity one with a 1750 lb. load capacity with 13 inch tires and unless I removed a leaf spring or 2, I wouldn't even think of using it to transport any of my paddlecraft.
 
As I stated, the biggest concern is the trailer bounce. The reason for using the trailer over car topping: I need to transport some furniture to New York and hate hauling an empty trailer back home. Trying for a twofer.
I'll probably wait for the car top rack to get here and go get my canoe.
Thanks for all the help.
 
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