Customweld
WKR
You gotta shed that water at the top before it has a chance to pick up velocity. Outslope the road to the right ( looking downhill in the first picture) into that little depression. Water bars suck, especially when you plow snow. If you have a good blade man close, have him build a couple of nice, rolling dips to that outside. Rolling dips are gentle enough to plow snow through but deep enough to turn that water off your road. The recycled asphalt mentioned above is a great road base, especially if you have someone experienced in placing it properly.