Converting field with poor drainage

Any tips for starting out with a field thst has really poor drainage? I planted a few pine trees last fall since they were free to me and they all died due to being waterlogged. So I realized before I can even start planting things I have a drainage issue to address but I do not know where to begin. Is there any kind of cover crop that you'd recommend? Let it go wild? I've been slowly collecting trees and bushes and I need to start getting these things in the ground sooner rather than later.

So three ideas come to mind:

1) Gradient.

Is the land flat or nearly flat? Could it be gently reshaped to allow a few catchment areas? Think of it like wet weather ponds that slowly let the water seep in, but leave the rest of the area dry enough to work with.

2) Trees and pasture can work well together. Plant some thirsty trees to help draw up the water and to provide some shade. This will have the impact of putting down roots that will help get the water down to the subsoil layer too.

List of Standing Water and Wet Soil Trees All of the trees listed below will flourish in wet areas, even standing water: Atlantic White Cedar Bald Cypress Black Ash Freeman Maple Green Ash Nuttal Oak Pear Pin Oak Plane Tree Pond Cypress Pumpkin Ash Red Maple River Birch Swamp Cottonwood Swamp Tupelo Sweetbay Magnolia Water Tupelo Willow  https://www.gardeningknowhow.com/ornamental/trees/tgen/wet-soil-trees.htm

3) Do a soil test and see if you have enough organic matter in your soil. If you have compacted clay, it would have trouble draining. Additives can help you nudget it n the right direction. Wood chips, Compost tea, or even lime/ash dust could help speed up the transformation. There are some great soil building threads here on permies and a resident guru RedHawk.

Depending on your soil and topography, cutting trees could actually make your waterlogged soil worse. It depends on whether your water cannot travel over the soil, or it is because it is just plain waterlogged soil. If it is the latter, then by cutting trees that are sucking up copious amounts of water, you cause the water in the soil to rise. This would require cutting a lot of trees though. I cut a lot of forest and convert it into fields, BUT I do not get this effect because I grade the soil, and so what was once rough and bumpy, tree infested forest, is smmoth, and so water flows across the land and into the swales that I create. IT is a huge difference then in just cutting trees.

You never asked, but if you are looking for a type of tree that survives with very wet roots, Black Spruce will grow. The only problem is, it grows very slowly. I planted some in 1996 or so, and they are no more then twenty feet high, and 4 inches in diamter. But they are growing!

It is always much easier (and cheaper) to work with what you have, rather then to try and change it. BUT it would not be impossible to install field tile (cheap 4 inch plastic drain pipe that comes in 100 foot rolls) and drain the area. This may, or may not be illegal. It is perfectly legal to use any land for agricultural use, however wetland cannot be converted to tillable land. So that pretty much means grazing only.

I made this video recently about a similarly waterlogged area on my property.

I dug a trench around an existing pomegranate tree and piled the dirt in a mound with the tree at the center. If the trees haven't been planted yet, the mound could be built first with the tree planted normally at the top.

It has really helped in just the few weeks it's been so far. The trees leaves are super green and healthy, and it's putting on a lot of new growth!

This may not be as feasible with a large number of trees, but if you're planting a few at a time it should be doable. Hope this helps!

hau Cassondra, the place to begin is observing how the water flows over the land, where it collects, where it doesn't collect, then you have the information to start thinking about how best to control that water so it goes where you want it to go (into the soil).

In swampy land, others have given you a good list of trees that will not only survive, but thrive and also help dry out some of the land. There have also been great tips offered for how to plant trees with success in such areas.

Before you plant anything though, you need to discover the best method for your area for controlling the water and do any earthworks needed to that end.
If you try to start planting without going in the right order, you might find that you have to undo all that you just finished.

Redhawk