Blue Runner hinted at something to check......there are drain holes in the tracks that can get clogged over the years and cause water to go the wrong way....check them.
Mine leaks when on the trailer with the bow raised, but not when sitting level in the water.....so when I have mine sitting on the trailer, but uncovered, I dont jack up the bow very high, just enough to keep water flowing out of the cockpit if it rains.
Heres a couple pics of the drain you are looking for.
From inside:
From outside:
I agree, if you want to keep whats in the boat going down the road, tie it down
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Stay Safe!
Sold - 1984 V-20 Cuddy with a 2003 Johnson 140 hp gas sippin 4-stroke.
1995 Ranger 250C with a 2015 Suzuki 300 hp 4-stroke.