What kinda machinery do you prefer to use for this work? I have to dig a mile or so of swales this year for a contract I got on my property.

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For smaller projects like this I use an A-frame I built a few years ago to mark contour. Then follow the line with a walk behind tiller to loosen the soil. Once loose, you can easily use a square shovel to “pump and dump” the soil on the downhill berm. You can get pretty accurate this way. Anything longer than 100-200ft is recommend a tractor or skid steer. Unless you have a few other people to help.