Orphan Train

Content Warning: This section of the guide contains discussion of racism and mental illness.

Gather initial thoughts and broad opinions about the book.

1. What was your initial reaction to the dual timeline structure of Orphan Train? Did you find yourself more drawn to Vivian’s historical narrative or Molly’s contemporary story, and what do you think Kline achieved by presenting both perspectives?

2. How did the novel’s portrayal of the orphan train system compare to your previous understanding of this historical practice? What aspects of this history were most surprising or affecting to you?

3. Orphan Train shares thematic elements with classic stories about displaced children, such as Anne of Green Gables (which appears in the novel itself). How does Kline’s approach to depicting orphaned characters compare to other works with similar themes you’ve encountered?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. Throughout the novel, both Vivian and Molly struggle with identity and belonging. How have your own experiences with adapting to new environments helped you relate to their stories? What aspects of their identity journeys resonated most strongly with you?

2. The concept of “portaging” is central to the novel—the idea of carefully choosing what to carry forward and what to leave behind during life transitions. What do you think are the most important things for a person to carry with them through life’s transitions? How does your answer relate to what Vivian and Molly choose to keep?

3. Molly uses her Goth appearance as armor against the world, while Vivian uses her wealth and isolation. What protective mechanisms have you observed people develop in response to difficult experiences, and when might these defenses become limitations?

4. Both Vivian and Molly are deeply affected by objects from their past—Vivian’s Claddagh cross and Molly’s charm necklace. What objects in your life hold special meaning, and how do they compare to the symbolic items in the novel?

5. The relationship between Vivian and Molly evolves from one of obligation to genuine friendship. What qualities make their unlikely friendship work, and how does their relationship compare to meaningful connections in your own life?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. The novel portrays how Vivian’s Irish heritage and Molly’s Indigenous Penobscot background shape their experiences in America. In what ways does Orphan Train illuminate the treatment of ethnic minorities throughout different periods of American history, and what parallels do you see to contemporary social issues?

2. Orphan Train contrasts the historical orphan train system with the modern foster care system through Molly’s experience. What systemic problems in caring for displaced children seem to persist across time, and what progress do you identify between these two eras?

3. When Vivian recalls her family’s immigration, she notes the signs that said no Irish people should apply. How have patterns of prejudice against immigrants evolved or remained consistent from Vivian’s time to the present day? What factors contribute to these attitudes?

Dive into the book’s structure, characters, themes, and symbolism.

1. How does the symbolism of turtles—which Molly explains “carr[y] their homes on their backs” and are “exposed and hidden at the same time” (88)—reflect the central themes of the novel and the development of both main characters?

2. The novel employs dual timelines and narrators. How does this structure enhance the parallels between Molly and Vivian’s experiences, and what insights does it provide that a single timeline couldn’t?

3. Consider the recurring motif of names and naming in the novel. Niamh becomes Dorothy, then Vivian; Dutchy becomes Luke. What does the changing of names represent for these characters, and how does it reflect their evolving identities?

4. How do specific settings in the novel, such as Vivian’s attic, the orphan train, and Molly’s various foster homes, function symbolically as well as literally in the narrative?

5. The author uses concrete objects (Vivian’s Claddagh cross, Molly’s charm necklace, the items in the attic) as vehicles for memory and connection. How does this technique of attaching meaning to physical objects enhance the storytelling?

6. Molly steals a copy of Jane Eyre from the library, a novel about another orphaned girl who faces hardship but eventually finds connection. How do you think Molly’s and Jane’s journeys parallel each other, and what might have drawn Molly to this particular book?

Encourage imaginative and creative connections to the book.

1. Write a passage that envisions Molly’s future after the novel ends. Describe a scenario that builds on her growth and newfound connection with Vivian.

2. Imagine an alternate meeting between Vivian and Molly. What if they had met when Molly was younger or Vivian was older? How would a different timing of Vivian and Molly’s meeting have changed their relationship? 

3. The novel explores how trauma affects people’s ability to form attachments. Sketch out a public awareness campaign addressing the needs of children in the foster care system. What would you include, based on what you’ve learned from Molly and Vivian’s experiences?

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