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The location of John Clark's plantation, though fictional, was carefully planned out to coincide with actual settlements and waterways. His land is set about seven miles east of Oxford and a little south along the Miles River, which is a tributary to the larger Choptank River beyond.
Old Indian trails, as mentioned, really did exist. Some that led to the coast or a river's edge were called rolling roads because of the planters rolling hogsheads of tobacco down them to where they could be loaded onto barges or ships. This also could be where the phrase, 'Let's get rolling', originated which means that it's time to 'get to work' or 'get going'.
Tobacco quickly exhausted the soil. To ready new areas for planting more quickly, men sometimes stripped a length of bark from around the perimeter of the trees, as John did, so that the trees would die and drop their branches. This allowed sufficient sunlight in, so that the crop could be planted among the trees and still thrive.
Stone boats were real as well, although I’ve not been able to establish exactly when they came into existence. They were wooden structures, similar to a sled, which were dragged behind a horse and were useful for hauling items such as rocks.
The worm fence, or snake fence, mentioned in A Willing Heart is historically correct also, as is moving it from field to field and using it to fence animals out rather than in. Livestock really did run free in those early days, and were marked for identification purposes. If a pig's ear was notched, as was the case in the story, the shape of the notch would indicate the owner of the animal.