Anne of Windy Poplars takes place over the three years between Anne's graduation from Redmond College and her marriage to Gilbert Blythe. While Gilbert is in medical school, Anne takes a job as the principal of Summerside High School, where she also teaches. She lives in a large house called Windy Poplars with two elderly widows, Aunt Kate and Aunt Chatty, along with their housekeeper, Rebecca Dew, and their cat, Dusty Miller.

During her time in Summerside, Anne must learn to manage many of Summerside's inhabitants, including the clannish and resentful Pringle family, her bitter colleague Katherine Brooke, and others of Summerside's more eccentric residents. Additionally, Anne befriends the young and lonely Elizabeth Grayson, a motherless member of the Pringle family who lives next door to Windy Poplars. She frequently visits Marilla at Green Gables.

Lucy Maud Montgomery, OBE (November 30, 1874 – April 24, 1942), published as L.M. Montgomery, was a Canadian author best known for a series of novels beginning in 1908 with Anne of Green Gables. The book was an immediate success. The central character, Anne Shirley, an orphaned girl, made Montgomery famous in her lifetime and gave her an international following.