Planting in a woodchip/sawdust log landing? How Early to get rye to overwinter?

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The chipping machines are an entire trailer.

This is what they use up there, cbi 8400 1200hp motor.

 

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I'll give it a shot, I think the deeper area will take a few more years, but I'll lime as much as I can and pick out the more ready areas.

I plant where I can up there. Also, nearby there's some good wide lanes I can keep clean too.