Chester the Chesapeake Books in Order

Chester enjoys a home where he can run, dig, and swim until a large dog and a kitten change his familiar world. Told from his perspective, the story follows his adjustment and development into a therapy dog.

Chester recruits his brother Russell to help a newly arrived dog discover the pleasures of summer. Their shared adventures introduce the newcomer to seasonal fun, while Chester's narration emphasizes companionship, acceptance, and the care dogs offer one another.

Chester, Russell, and Putt-Putt wake to find their home and surrounding trees covered in snow. A day of outdoor play and a nursing-home visit ends with Chester settling down, comforted by the presence of his loving family.

Chester expects a small female dog to join his family, but the newcomer turns out to be his brother Buck. The unexpected arrival brings surprises as Chester learns to welcome another pet into the household and share his home.

Chester, Putt-Putt, and Buck encounter several Santas during the Christmas season and wonder which one is genuine. As the dogs learn about the holiday, Chester searches for the real Santa so he can share a secret.