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I've ridden dirtbikes all my life but never road bikes. I'm looking at buying a 1989 Yamaha Route 66 (250cc). Only 8,000 miles on it and very clean. I'm going to use it, or whatever bike I end up buying, to travel to work this summer. I travel anywhere from 200 to 400 miles to get to work for the week and stay in the nearest town, I work highway construction. So I'm going to build a small trailer to pull behind my bike. The trailer weight will be approx. 85 pounds, then I will load my clothes and food for the week and a couple gallons of gas on the trailer. Overall the weight of the trailer fully loaded won't be over 150 pounds. Is the 250cc Route 66 enough to pull this trailer?

P.S. I only weigh 150lbs and I drive very safely.

Thanks for your responses.
 

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I think with a bike that small you will have stability issues at speed. Also you will have trouble breaking, not so much because of the weight but due to that bike being tiny for pulling a trailer.
 

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The Rebel and Rt 66 were originally made to satisfy a 16yo fantasy of having a chopper- a REAL bike. Unless your height is less than 5' 6", you will be miserable riding over one mile.
 

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I definitely would not be using that bike to pull a trailer, then again I don't know what motorcycle I would recommend for pulling a trailer beyond maybe a Goldwing.
 
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