“Plowed the head land this morning and then farther rolled the furrows and J got the piece dragged once over to day. Has been a pleasant day.”
A headland is a point of land, usually high and often with a sheer drop, that extends out into a body of water. The word is often used as a synonym for promontory. A headland is often referred to as simply a head, either in context or in names such as Beachy Head or Koko Head.
Our girl is not located on the water. In her case she must just mean an out cropping of land on a hill.