The road seems to get longer and longer as the wayward Pinkamena Diane Pie travels from town to town in this tale of woe, devastation, and musicianship. Ostracized from society because of her peculiar tendency to lure children away from their homes (with a strange propensity for orphans) with her hypnotizing music, the Gypsy Bard finds that life is a continuous struggle, so the only way she can cope with it all is through the seamless accompaniment of run-away foals.

Long into the future of Equestria, after all of the familiar faces that we have come to know have passed on, there exists a crucial moment in time where the following millennia will be forever influenced by the events which take place. The technologically advanced society has developed a way for ponies to travel to other planets in their respective cosmos, but there are some "neigh"-sayers who claim that such travel would violate the traditional notion of Magical Attachment to their current homeworld. With the two factions feuding with each other, the future of the Equestrian society is left in the balance.

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.

After the events of Season 2 of My Little Pony: Friendship is Magic, the six good friends gladly accept a calm state of peace and harmony that has seemed to settle across the land of Equestria. A new colt arrives from Canterlot University on a study-abroad program similar to that of Twilight Sparkle, and has no problems integrating himself into the tight circle of friends due to his near-perfect mannerisms, dedication to hard work, and surprisingly intellectual studies. The lovely status quo of Ponyville, however, starts to teeter out of balance because of everypony's possessive obsession with this new pony, and because a much darker enemy than anypony could have ever imagined begins to creep up over the veil of victory.