Timothy Jessup is a wise and sensitive 11 year old orphan boy. He has an inseparable friend, a beautiful and fiery toddler Gabriella, who is called Lady gay, and a faithful dog named Rags. They are forced to take care of themselves and Timothy takes the role of guardian for Lady Gay. Forces of circumstance bring the children to White Farm where they are, reluctantly and quite temporarily, taken in by two older women. During their stay at the farm, they are both dealing with anguishing issues from their past.

Kate Douglas Wiggin (1856-1923) was an American educator and author of children's stories, most notably the classic children's novel Rebecca of Sunnybrook Farm. She started the first free kindergarten in San Francisco in 1878 (the Silver Street Free Kindergarten). With her sister during the 1880s, she also established a training school for kindergarten teachers. Kate Wiggin devoted her adult life to the welfare of children in an era when children were commonly thought of as cheap labor.