Oh, I love sailboats. Great picture. Not really any obvious way I'd try and suggest changes. I also see how you fit this into the road challenge, but the shot is really more about sail boats.
Seems a bit static and flat. A more interesting angle of the bridge, not centred and lined up with the horizon like that, would be a lot more appealing.
This is a very nice harbor shot... I love the railroad bridge... i think that railway photogrpahy is becoming one of my favorite subjects... When I look at this photo and think of "On the Road", I have a difficult time determining how this photo conveys that concept to me. If I were looking at this shot, not knowing anything about this challenge, I would think that the boats and the water were the main subject. This doesn't strongly convey the challenge concept to me...
I like this bridge and I think I see what you're after. The angle is good, but the overall composition might look better if the distractive foreground could be mostly cropped out. Maybe a tigher crop on the bridge shot higher? Good exposure and nice subject!