Any advice on how to fix this?

[freewookie]

Tin horn, French drain, pond,???

I leveled it a bit which has helped keep most of it from the gate posts.

 

[dieselbeef]

electric gate opener

 

[Gary Fowler]

I may be wrong but from the photos it looks like the road builder created a dam. He should have put in a culvert under the road at that point.
Perhaps it can drain into a road ditch and get further from the gate and eventually go to a creek or ditch further down the road. If not, then the only option is to cut the road and place a culvert there so it can drain to the lower side (to the left in photo)

 

[EddieWalker]

I agree with everything Gary said. You need a culvert to get the water to the other side of the road. It's incomprehensible that somebody would spend the money to pave a road, but not spend another hundred bucks to put a culvert under it. Is there a chance that there is a culvert there, but it's plugged up and grass has grown over it? I would look real hard for an existing pipe before I tore up that pavement.

Eddie

 

[freewookie]

Yeah that's what I was thinking and fearing. They put one in closer to the house but that's only one for a 1/4 mile drive. Still befuddles me that they put the road at the bottom of the pasture.

 

[freewookie]

What about brining in enough dirt to level off with the road? Would the rain then runoff over the road?

 

[square1]

Is there a ditch along the perpendicular road (at the top of the first pic) you can drain it to with a tile?

 

[freewookie]

Is there a ditch along the perpendicular road (at the top of the first pic) you can drain it to with a tile?

Yes that's a county and have a ditch with cement runners. A tile?

 

[freewookie]

Yes that's a county and have a ditch with cement runners. A tile?

County road I meant.

 

[square1]

A tile?

Something along these lines.



Does it ever dry out? Running a sub soiler through the area might help immensely.
http://www.tekura.school.nz/departments/horticulture/ht108_p9.html