1. What gives Elizabeth the courage to fight for the vindication of women? How does her vision of the New World compare to that of most early American immigrants?
2. How is Nathaniel affected by his past? When he recalls his previous wife’s desire to be white and his desire to be red, what cultural ideals is he describing?
3. Discuss the Native American notion of land as a spiritual homeland, not a commodity that can be bought and sold with money. How does this compare to the way Judge Middleton and Richard think of land? Does Judge Middleton think of Elizabeth as property too, or is he simply looking out for her best interests in a time when single women faced significant challenges?
4. How did the colonists featured in Into the Wilderness justify their personal quest for freedom while advocating slavery? How did Elizabeth’s father reconcile his upbringing with the beliefs of his fellow citizens?
5. Why was Elizabeth hesitant to begin a relationship? Would you have been tempted to marry Richard? How would you have fared in a marriage that deprived you of property rights?
6. What common ground do Richard and Nathaniel share? What accounts for their very different approaches to life, despite their similar history?
7. What does Julian’s relationship with Kitty say about him? What accounts for their attraction to each other? How does Kitty’s pregnancy change their lives, and the lives of those around them?
8. How is Hannah affected by having Elizabeth in her life? What does Elizabeth teach her about feeling valued?
9. How is Elizabeth’s life shaped by the death of her mother? How does the memory of her mother affect her idea of womanhood? Does Julian react differently to that aspect of their family history?
10. Elizabeth and Nathaniel are assisted by many enlightened friends, such as the Schuylers. Why do some members of their community accept unconventional people, while others reject them? Even today, in the modern world, what are the roots of these two mindsets?
11. Discuss Elizabeth’s relationship with Julian. Are their differences due to nature, or the way they were raised (nurture)? What does it take for Julian to redeem himself in the end? Or does he?
12. What power and limitations do Curiosity and Galileo possess as freed slaves? How do they influence the Middleton family? For whom is the settlement of Paradise a paradise?
13. How does the arrival of Aunt Merriweather change the way Elizabeth’s family interacts? What is Aunt Merriweather able to see in her niece that others overlook?
14. What is the impact of the additional revelations about Nathaniel’s identity? Which of the legacies in his ancestry matters the most?
15. What did you discover about this chapter in American history? How are the quotations from Thomas Paine and Mary Wollstonecraft relevant today?
16. What do you predict for Elizabeth and Nathaniel’s future in Dawn on a Distant Shore? United in marriage, what are their greatest strengths and vulnerabilities?