All four stories involve the maturation of Jody Tiflin, a boy of about ten when the action opens. He lives on his family’s ranch with his father, Carl, his mother, Ruth, and the hired hand, a middle-aged cowboy named Billy Buck. From time to time they are visited by Jody’s grandfather, a venerable old man who led one of the first wagon trains to California.
“The Gift,” the first story in the sequence, concerns Jody’s red pony, which he names Gabilan after the nearby mountain range. The pony soon becomes a symbol of the boy’s growing maturity and his developing knowledge of the natural world. Later he carelessly leaves the pony out in the rain, and it takes cold and dies despite Billy Buck’s efforts to save it. Thus Jody learns of nature’s cruel indifference to human wishes.
In the second section, “The Great Mountains,” the Tiflin ranch is visited by a former resident, Gitano, an aged Mexican-American laborer raised in a hacienda that is no longer standing. Old Gitano has come home to die. Carl persuades Ruth that they cannot take Old Gitano in, but their dialogue proves pointless. Stealing a broken-down nag significantly named Easter, the old man rides off into the mountains to die in dignity. Again, Jody discovers some of the complex, harsh reality of adult life.
In “The Promise,” the third story, Jody learns of the intricate connections between life and death, when, in order to get his son another colt, Carl breeds one of the mares. But the birth is complicated, and Billy Buck must kill the mare to save the colt.
The themes of death and life converge naturally in the first three stories, preparing readers for the final section of the sequence, “The Leader of the People.” This story brings the sequence to an end with another vision of death and change. Jody’s grandfather comes to visit, retelling his timeworn stories of the great wagon crossing. Carl Tiflin cruelly hurts the old man by revealing that nobody except Jody is really interested in these repetitious tales. The grandfather realizes that Carl is right, but later he tells Jody that the adventurous stories were not the point, that his message was “Westering” itself. For the grandfather, “Westering” is a force like the frontier, the source of American identity; now with the close of the frontier, “Westering” has ended. Westerners have degenerated to petty landholders such as Carl Tiflin and aging cowboys such as Billy Buck. In his grandfather’s ramblings, Jody discovers a sense of mature purpose, and by the conclusion of the sequence he, too, can hope to be a leader of the people.