I agree with Neil, but I would probably start in the water and dry the bilge with a towel, and watch carefully. It is possible the drain plug area is leaking and it might require the added pressure of sitting in the water to leak. Plus it would be nice to know if it is say a tube connection whether it was port or starboard so you know what direction to tilt the trailer.
Very common for the drain plug bung to leak due to transom degradation/rot. Which of course just makes the leak bigger over time.
How much water enters in a set period of time? Like 5 minutes? 1 hour? 12 hours? 24 hours?
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