The oldest Penderwick sister, Rosalind, takes on the responsibilities of caring for her younger sisters in their mother’s absence. In addition, Rosalind is the only sister who shows emotion over the loss of their mother, and she keeps a photo of Mrs. Penderwick by her bedside at the cottage. Batty says, “She takes care of me because Mommy died when I was a tiny baby” (68). Rosalind hides her grief from Batty, but after Skye tells her the awful things Mrs. Tifton said about their mother, she can’t conceal her anguish. Since she oversees Batty’s nightly bedtime routine, Rosalind uses the time to impart stories about their mother, giving Batty a sense of who she was. Rosalind is the only sister who maintains a close connection to home during their trip, often thinking of her best friend, Anna, and writing her describing their summer adventures, most notably that she fancies Cagney, the handsome older boy who tends Arundel’s gardens. Rosalind doesn’t connect deeply with Jeffrey like her sisters do. However, when he runs away from home, she presides over the sisters’ meeting to help him develop an escape plan.

Rosalind misses out on many of her sisters’ and Jeffrey’s adventures to help her father and, once she falls for Cagney, to spend time with him and learn about his interests.