Gather initial thoughts and broad opinions about the book.

1. The Winterhouse hotel is filled with puzzles, strange artifacts, and hidden secrets. What was your overall impression of this setting, and which part of the hotel would you have wanted to explore first?

2. How does Winterhouse fit into the tradition of middle grade puzzle mysteries? If you’ve read similar books, like Trenton Lee Stewart’s The Mysterious Benedict Society, how did Elizabeth’s adventure compare?

3. What did you think about the book’s blend of cozy mystery and dark supernatural fantasy? Did you find the balance effective, and why or why not?

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

1. Elizabeth finds a true sense of belonging at Winterhouse after a lifetime of neglect. Think about a place or a group of people that made you feel truly welcomed. What elements created that feeling of home for you, and what effect did this experience have on you in the longer term?

2. The friendship between Elizabeth and Freddy forms over a shared love of puzzles and wordplay, and they come to trust each other deeply. What shared interests have helped build relationships in your life? 

3. Throughout the story, Elizabeth copes with her difficult life by making lists, such as “Reasons Why I Do Not Like My Aunt and Uncle” (6). What did you think of this coping mechanism? What are your ways of making sense of the world when it feels confusing or unkind?

4. Norbridge acts as a kind, if secretive, mentor to Elizabeth. Think about a mentor or positive adult figure in your own life. What qualities made them so important to you?

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

1. The central antagonism between Gracella and Winterhouse turns on a history of female disinheritance. What does the book have to say about rightful legacy, especially in the context of patriarchal structures of ownership?

2. Winterhouse engages with the theme of found family as well as kinship. How does this reflect the modern concept of family and the various forms which this can take?

3. The novel strongly promotes the idea that intellectual curiosity is a form of power. What message do you think the book sends about the importance of logic, reading, and problem-solving skills for navigating a complex world?

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

1. How does the author build suspense around the character of Norbridge Falls? Use examples to analyze how your expectations were set up and/or subverted.

2. How does the book use color as an emotional signal and to build connection for the reader?

3. When Gracella offers Elizabeth a partnership, Elizabeth is tempted. Why was this moment important for the story? Did you anticipate Elizabeth’s choice and why?

4. How does the Hiemses’ crate act to create suspense and dread in the narrative? What parallels in gothic or supernatural fiction does this draw on?

5. How does Ben Guterson’s book compare to another well-known middle grade fantasy series opener, like Harry Potter and the Sorcerer’s Stone? What similarities or differences do you see in how they introduce their magical worlds and young heroes?

Encourage imaginative and creative connections to the book.

1. Imagine you’ve been hired by Norbridge Falls to add a new puzzle-based attraction to the Winterhouse hotel. What kind of puzzle would you create, where in the hotel would it be located, and what secret might it unlock?

2. The book that Elizabeth finds, A Guide for Children, contains peculiar chapters on things like games, secrets, and deceiving adults. If you were to add a new chapter to this mysterious book, what would its title be and what kind of “secret” knowledge would it contain?

3. At the end of the story, Elizabeth starts reading a new mystery, The Secret of Northaven Manor, which she thinks will be her “kind of story” (370). Plot and write the opening scene for this novel, considering how to pique Elizabeth’s interest.