Eleven-year-old Caddie Woodlawn is a tomboy growing up in the 1860s who would rather plow than sew, and she spends the bulk of her time chasing her brothers around the farm, having escapades in the woods. Her mother and sisters do not understand, nor approve, of her rough-and-tumble life. She spends her time stringing one adventure to the next, adventures filled with practical jokes and heartfelt events too. Despite the fun that Caddie has with her brothers, it is eye-opening to see how often death was a part of life back then, between a fall through the ice, settlers planning an attack on the Indians, and a prairie fire. When Caddie's "perfect" cousin Annabelle visits from Boston, Caddie must face her future and the growing up she's always resisted.
Set during the same time period as Little House in the Prairie, there are many parallels to be drawn here. Although the Woodlawns do not face the same suffering that the Ingalls do, from lack of funds, crop failure, and settling in the wrong territory, the pioneering spirit and work ethics are nearly identical. Rather than being a story of survival, like the Little House books, Caddie Woodlawn is more a story of a tomboy's adventure toward adulthood. Caddie Woodlawn is the author's grandmother, who raised her through childhood, and it's easy to see that the author admires Caddie's spirit.