1. Grandma Dowdel deceives the reporter from the city about Shotgun Cheatham. Can her falsehood be justified? Why does she fabricate the story? Is lying ever permissible? Elaborate on your response.

2. The concluding sentence of "Shotgun Cheatham's Last Night Above Ground" references various types of truth. Read the final paragraph and analyze what Peck implies in the last sentence. Is this concept still relevant today?

3. In "The Mouse in the Milk," Grandma tells another lie. Do you notice a recurring theme here? What lesson is she imparting to her grandchildren through this behavior?

4. Mr. Cowgill disciplines his boys after Grandma apprehends them in her kitchen attempting to steal her gun. What are your thoughts on this? How do your parents discipline you when you deserve it?

5. In "A One-Woman Crime Wave," Grandma engages in several actions that the sheriff views as illegal. List these actions. Is this the first instance of such behavior? How can you tell?

6. At the conclusion of "A Day of Judgment," Joey questions Grandma and makes a confession. Discuss her reaction. If she swapped pies to win but did not succeed, what does her statement mean? Why did she switch the pies?

7. Was it inappropriate for the men at the Piatt County Rod & Gun Club to be drinking? How did Grandma leverage their embarrassment to her benefit?

8. Why does Alice tell Joey that she doesn’t believe Grandma is a good influence on them? Who has a significant influence in your life? Why does that person hold such influence?

9. Why do Joey and Alice's parents send them to Grandma Dowdel's for a week each summer? Do you visit a relative or attend a camp during the summer? What experiences have you had that are comparable to their visit? Are there any similarities between what you do and learn there and what Joey and Mary Alice experienced at Grandma's?

10. Do you have a grandparent or another older adult in your life like Grandma Dowdel? Draw a comparison between the two.

11. How does gossip distort the truth? How did gossip distort the truth in A Long Way from Chicago?

12. If Mrs. Wilcox is Grandma's greatest adversary, why did she participate in the charade with the hat and quilt that helped Mrs. Wilcox reclaim her home?

13. When Joey and Mary Alice searched the attic for items for the church rummage sale, they discovered old valentines. What did these valentines reveal about Grandma Dowdel? Why was this surprising to them?

14. Grandma makes the statement, "A rumor is sometimes truth on the trail." What does she mean by this?

15. What is your reaction to the final chapter, "The Troop Train"?

16. Discuss the episodic format Peck uses to present this story. Why is this structure effective for the narrative?

17. How might A Long Way from Chicago have differed if the children's parents had spent one of the summer vacations with them at Grandma Dowdel's?

18. How does the novel explore and develop the themes of truth, justice, and ethics? What defines truth? How is justice characterized? What constitutes ethics? What serves as the ultimate authority for truth, justice, and ethics?