Book Club Discussion

Secrets of Windy Hill Book Cover

The Secrets of Windy Hill

Join Jesse on his tantalizing journey from bustling New York City to the wonders of rural island life, leading him straight into a nest of bedeviling secrets on Windy Hill Farm.

As he encounters heart-rattling escapades, unexpected mysteries, and menacing perils, he tries to hold fast to his everyday magic – shining out from a heart that is still becoming, learning to trust, to love and lose … and love all over again.

Use the questions and ideas below to help find the stardust and Light in Jesse’s story and in your own.

Discussion Questions

  1. Dearie is the narrator for this story, and her intimate relationship with Jesse is clear when he hears her voice inside him. She explains his predicaments and reminds him to always keep his Light on. What does this mean to Jesse? How does he use his Light to change his attitude? Does it change his situation? Give examples from NYC, along his journey, and at Windy Hill Farm.
  2. When does Jesse perceive why he is truly leaving New York City? What does this mean to Jesse as he moves through his story?
  3. Jesse has prepared for his quest to find his ‘disappeared’ grandmother, Lady Jessica, but things do not all work out according to plan. What are some of the mishaps he encounters along his journey and at Windy Hill Farm?
  4. Regan Murphy tells quite a tale about the women of Windy Hill Farm: Avery, Susan, Jane and Jessica. He says they are all bad apples. Why? He calls Jessica the Black Widow. Is this an apt name for Jessica? How does Jesse’s arrival change this narrative?
  5. Why are Peter Murphy’s words about the Depression important in understanding Jessica – as Connor learns when they meet face to face? How do events from the Depression later connect to the characters of Tim and Tina Braedon?
  6. What does Jesse think of Miss Lily when he first meets her? When did you feel his – or your – attitude toward her changing?
  7. Discuss how and why Jesse changes Jessica’s name to Gemma. How does this impact her? Do you think she grows into her new name?
  8. How do Greta and Matts help Jesse find his way on the farm? What is the arrangement between Gemma and Margarethe and her children? On the farm? At the market?
  9. What are the secrets, mysteries, and riddles Jesse finds in the gadgets and the people and the history on Windy Hill Farm? Discuss how some of them impact Jesse’s story and how some of them are resolved.
  10. Jesse still loves his word-play. Give examples of his fun or intriguing Spoonerisms, Kangaroo Words, malapropisms (‘gargoyling’ his words), riddles and song.
  11. Who are some of the characters Jesse suspects of stealing from Windy Hill Farm? Give examples of who they are and why Jesse suspects them.
  12. How does Jesse find his Light after he discovers the truth about who Miss Lily really is, especially when he discovers the evidence against her? What is the magic that reminds him?
  13. Music plays an important part in Jesse story. What are some of the songs or compositions that stand out? How do they help frame the mood and attitudes? How does Rachmaninov’s personal story and music help Jesse?
  14. With family or friends, how does Jesse behave like a “love-y – dove-y” cupid?
  15. Does Dearie’s stone or Mac-Elliot’s silver dollar bring Jesse luck? Is there a treasure on Windy Hill Farm? What is The Greatest Thing? What mysteries do you think Gemma and Jesse will share next?