- Name: Miss Winston (No first name given)
- First Appearance: Kirsten Learns a Lesson
- Age: 19 years old 
Very little is known about Miss Winston's background. However, it is revealed during the course of her appearances in the series that her father is a ship captain and that she is originally from Camden, Maine.
Miss Winston is originally from New England. At first Kirsten doesn't like her very much because she is strict and not very understanding of Kirsten's difficulties learning English. Later Miss Winston moves in with Kirsten's family and as Kirsten gets to know her better, she warms up to her.
In The Books
Kirsten Learns a Lesson: A School Story
Miss Winston introduces herself to the students of Powderkeg School and informs them about Mr. Coogan's injury. She asks each student to introduce themselves; upon Kirsten introducing herself, Miss Winston corrects Kirsten's diction, telling her to say "ma'am" after her name.
Miss Winston initially gives Kirsten a verse from The Doves to recite, and becomes frustrated at Kirsten's efforts and attempts to remember and recite the verse. During Miss Winston's first night at Olav and Inger Larson's house at dinnertime, she talks about her parents' home in Maine, about her father's job as a ship captain, and her decision to travel and become a teacher. After dinner, she brings out an impossible bottle with a model of a three-masted ship to show the Larsons. Kirsten's story about how her family sailed on the Eagle on their way to America inspires Miss Winston to give Kirsten a different verse, from The Rime of the Ancient Mariner, to recite for class.
Upon Kirsten's successful recitation of her verse, Miss Winston allows Kirsten to go fetch some water. Due to the time Kirsten spent with Singing Bird after the recitation, by the time Kirsten returns to the schoolhouse with the water, Miss Winston makes a lighthearted joke about Kirsten having found a ship and sailing back to Sweden. She also tells Kirsten about the Reward of Merit left in her reader.
Kirsten's Surprise: A Christmas Story
Miss Winston allows Kirsten, Lisbeth, and Anna to borrow her candles for the Saint Lucia wreath. She tells Lisbeth to measure Kirsten's head with some string before making the wreath.