In a simpler time, in a much simpler place, the aristocratic lifestyle of Winchester Grange fills its practitioners hearts and minds with grace and social status. The peace and stability of the community is threatened, however, when The Duke of Alicorns, Celestia's brother, takes up residence there and ensues the construction of a castle manor right in the middle of the territory. Canterlot Castle, he calls it, is predicted by many of his peers to become the center for all cultural activity all across Equestria, and may even become the future residence of his sister. A story of inevitable change and adjustment, Grazing on the Hilltops of Winchester Grange follows the life of young Gabarlile Rudge, the son of the richest pony in the Grange, and the eventual receiver of his father's fortune. When the time comes to forfeit the ownership of the entire land to The Duke, Gabarlile must make a choice between tradition and progress.