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, she has a sister, 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
Kirsten trusts Miss Winston with their plans for their Saint Lucia's day surprise, as she had been reminiscing the Christmas parties she had back in the east coast. Miss Winston allows Kirsten, Lisbeth, and Anna to borrow her candles for the Saint Lucia wreath and offers to hide the crown in her trunk, saying she liked surprises. She tells Lisbeth to measure Kirsten's head with some string before making the wreath.
Miss Winston stays up with the rest of the family to wait for Kirsten's and Papa's return. She is the only one who isn't in her nightclothes, though her hair is undone. Miss Winston is the one to tell everyone to close their eyes and turn down the light in preparation for Kirsten's entrance into the room.
Happy Birthday, Kirsten!: A Spring Story
Miss Winston is still living with the Larsons and when a tornado approaches the cabin she brings her quilt with her into the cellar. In the cellar, Miss Winston tells the story behind her quilt, that her mother, aunts, cousins and sister had worked together to make this quilt for her as a reminder of home while she was gone. Miss Winston treasured it greatly, and looking at it was like getting a letter from home. Miss Winston agrees to teach the girls how to make a quilt, explaining to Kirsten's mother that quilting trained the hand and eye and it was very practical. Miss Winston is pleased by Lisbeth's suggestion that they work on their quilt during recess, stating where there's a will, there's a way.
Kirsten learns from Anna and Mary during their recess quilting session that Miss Winston would one day leave the Powderkeg school to move onto a different school. Mary states that she's had a different teacher for each year she's been at the school, but Miss Winston was the only nice one. Anna adds that Miss Winston often says that she liked it here, and Kirsten hoped she would stay. Anna suggests if Miss Winston did leave, that they add their quilt squares to her quilt as a reminder of them. When Mary points out that Miss Winston's quilt was already complete, Kirsten suggests they make a new quilt from scratch for her.
Miss Winston is at Kirsten's birthday party, where she pretends to be stern as she gets the girls into a circle. When Kirsten asks her Mama how she found the time to sew her new apron, Miss Winston whispers to her that where there's a will, there's a way. When the girls give Kirsten the quilt they worked on and Kirsten reminds them it was meant for their teacher, Miss Winston explains that she told the girls one quilt was enough for anyone. Miss Winston takes out a pen and ink for the girls to use to sign their names onto the quilt, and she writes on the quilt's border 'For Kirsten Larson on her tenth birthday'.