Miss Bessie is the cow that belongs Jess's family. Milking Miss Bessie is one of Jess's chores that he has to do for the family.

Readers are introduced to Miss Bessie in chapter one. Jess quietly exits his family's house at the beginning of the chapter in order to continue getting in his training runs. On his way out to the field, he has to pass Miss Bessie. She is awake, and Jess tells the cow to just go back to sleep. She doesn't. She wanders off to find a few green patches of ground to eat. As Jess makes his way over to the far end of the field, Miss Bessie follows him. Jess begins his sprint, and we are told that Miss Bessie, dumb as she is, knows to stay out of Jess's way.

Jess's job is to milk Miss Bessie every morning, and he is quite diligent and faithful about doing it. He is never really excited or glad to do it. Often, Jess is awake before other members of the family, and he often thinks that he might as well go milk the cow and get it out of the way. Despite the fact that he doesn't take much joy in the chore, the chore itself does allow Jess time and space away from his family, and Jess appreciates the alone time.