Henry Kitteridge hires a new assistant at his pharmacy. Olive and a fellow teacher give a shy student a ride home and Henry goes on a hunting trip. Later, Olive experiences a tragedy.

Kevin returns to Maine and Olive is able to convince him to stay over. At Christopher's wedding rehearsal, Olive clashes with the bride's mother.

After a dinner with friends, Olive and Henry make a pit stop that takes a chilling turn. Christopher suggests that his parents should get counselling and later confronts his mother about rebuking him throughout his childhood.

Olive goes to New York City to visit Christopher but gets put off by his wife's demeanour, receives bad news about Henry, and ends up developing an unlikely bond with Jack Kennison.