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I would imagine a two up Ultra would be able to pull that trailer. It probably outweighs the trailer by 2-300 pounds. What I don't like about pulling a trailer with a bike, is if you get into a situation where jackknifing is possible, that single rear tire will unload in a heartbeat and y'all will be going down big time.
The only design that makes any sense at all for a bike is a single wheel trailer that attaches at two points on the bike.
I pulled a small Calafia trailer from California to Arkansas years ago. It didn't weigh much but I still knew it was back there. On some roads, it would wiggle side to side and with the small 9" wheels, it would hop and jump over bumps. All in all, it convinces me to carry plastic and camp out at a motel.
We pull a Bunkhouse camper with very little problems, but "brake push" is sometimes felt. Ours weighs in around 300lbs. Once loaded with camping gear, we're at 350. Here's the new model:
The tear drop in the first post is possibly a Little Guy. They are sold at bike rallyes, and weigh about 800 lbs. No way would I want to be pulling that much, plus the effect of a side wind has to be tremendous.
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