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I was told that I do if the trailer weighs over 3,000 pounds. But is that without on the boat on it or with the boat on it?
Check with your DMV office for a factual answer. In Virginia though the answer to your question would be yes it is needed.

#1 by Boatin' in VA! on October 1st, 2009
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Check with your DMV office for a factual answer. In Virginia though the answer to your question would be yes it is needed.
References :
20+ yrs of boating…
#2 by Jeff on October 1st, 2009
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Wisconsin is an exception, the DMV there says that you do not need to register a trailer.
I had a friend that had a trailer from WI (with no registration) and drove it to Michigan and they gave him a hard time, but the cop wound up calling a WI cop friend and they told him it wasn’t necessary for WI trailers. The cop let him go.
References :
Lived there and sailed last summer
#3 by trunorth on October 1st, 2009
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In Minnesota if it rolls on public roads it must be licensed.
References :
Inland waters guru