1. When Miranda first returns to Greyfriars in 1969, she says, “I should approach the house like an old friend with whom you had quarreled long ago and since forgiven so far as to forget what the quarrel was about. But now I glimpsed the stone wall…I was eighteen again.” At the end of the novel, does Miranda still view Greyfriars in this way?

2. How is the locals’ relationship with Winthrop Island different from the Families’ relationship with the island? What do these differences tell us about the social structure of the island?

3. How does World War II affect the Island and its residents? Do you think it affects locals and Families differently? How does the power and status of the WASP elite change in the postwar era and how does this play out in the Islanders’ lives?

4. Several romantic relationships play out through the course of the novel. How does the unequal social status of the participants affect each relationship’s power dynamics, its course, and its outcome? Do we still see these dynamics playing out today?

5. “I’ll say this about the Island. The Families and the locals, they respect each other, which is more than you can say of a lot of places like this.” Do the locals and the Families really respect each other? How would you describe the relationship between the locals and the Families, and how does it change between 1930 and 1969?

6. In what ways have Miranda and Isobel changed since the passing of Hugh Fisher? In what ways have they stayed the same?

7. “Nobody ever says what they really mean. There is this vast fabric of tender little lies, and all the important things are unspoken. Boiling there underneath. We only bother telling the truth when it’s too small to count.” How does this statement hold true throughout the novel?

8. Everyone on Winthrop Island has a secret. Are the secrets the locals and the Families are keeping worth it? How would their lives be different if they weren’t carrying around these secrets?

9. What do you think happens to Miranda in the years following the novel’s end?