I allow taproot "weeds" in my orchard for breaking up the soil and nutrient accumulation (teasel, queen Annes lace, dandelion, fireweed, comfrey, etc.). I use a scythe to cut them right before they go to seed (except the sterile comfrey), to keep them from going too crazy. Allowing them to flower gives lots of food to my pollinators.
I also do not disturb the moles unless they get in my lawn. And even then I just use a hose to wash their dirt back down into the ground.
In other words, I let "nature" do most of the work for me.
Of course if you either are in a big hurry or you want your orchard to always look like a putting green, you'll need to use big machinery.
If you are trying to mechanically work it and depending on the type of soil, late spring, or early fall may be a better time, when there is some moisture in the soil but it isn't saturated.
A subsoiler or spader should do the trick to break up the upper crust without churning everything to dust.
Idyllwild
jafar
Marsha H
Viron
John S
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