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Vibration While Towing

Sounds like the trailer has a problem. How old is it and what type?
 






If you can rule out the trailer then I would check the rear wheel bearings, your truck shouldn't have bad bearings already but who knows and just the additional weight at speed could cause you to feel the bearings more if either is going bad.

I just had my left rear wheel bearing changed because it was worn out.
 






It is probably the trailer. I have the same issue every time I tow my boat. The boat and trailer are around 5500lbs. All 4 tires develop flat spots from sitting and it takes a few miles for the tires to warm up and round themselves again. For the first mile it almost feels like there's something REALLY wrong. My wife gets very nervous. After a few miles its gone though.
 






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