Anne Shirley, B.A., has left Redmond College for the sleepy little town of Summerside to begin a three-year principalship while her fiancé, Gilbert Blythe, finishes medical school. Her biggest challenge, by far, is seeing Gilbert so infrequently, with only letters to keep them connected. But that isn't all. Summerside is ruled by the "royal family" of the Pringles, and for some reason, they've decided they do not like Summerside's new principal.

As Anne settles into her cozy tower room at the Windy Poplars boarding house, she determines to win over the Pringles and leave Summerside in triumph. With the help of her land ladies, Aunt Chatty, Aunt Kate, and the formidable Rebecca Dew, she just might do it!