Patrick's Top 10 Books Where Characters Go Down the Rabbit Hole

An oddly specific trope I love in books is when there are characters who start out the story knowing how the world works and knowing who they are, only to descend slowly and gradually into a world that is foreign, disturbing, and unknowable. Whether it be literally transporting to some new place or simply learning truths about the world that shatter their perception of reality, there is something compelling about watching a character descend into the unknown. Here are ten books that follow characters who go down the rabbit hole and end up in wonderful/troubling surreal states.

Alice's Adventures in Wonderland By Lewis Carroll, Júlia Sardà (Illustrator) Cover Image
By Lewis Carroll, Júlia Sardà (Illustrator)
ISBN: 9781509897605
Availability: Unlikely to Be Available
Published: Two Hoots - June 1st, 2021

What better way to start off the list than with the big one? Alice's Adventures in Wonderland is what spawned the phrase "down the rabbit hole" and is literally all about Alice going down a rabbit hole and ending up in a bizarre and nonsensical world that she does not understand. It is a classic for a reason, the story is fun and the world of Wonderland is unlike anything else. 

The Trial: A New Translation Based on the Restored Text (The Schocken Kafka Library) By Franz Kafka Cover Image
ISBN: 9780805209990
Availability: NOT ON OUR SHELVES. Usually Arrives in 4-7 Business Days
Published: Schocken - May 25th, 1999

One day, an ordinary man named Joseph K. is accused of a crime he did not commit and he is forced to undergo an absurd trial process. Although it is not as fantastic as Wonderland, the surrealism of the bureaucracy and arbitrary rules of this society creates a feeling of being alone in an unknownable world. Watching Joseph K.'s character change as the process of trial endlessly continues is mesmerizing. 

I Am Not A Serial Killer (John Cleaver #1) By Dan Wells Cover Image
ISBN: 9780765327826
Availability: NOT ON OUR SHELVES. Usually Arrives in 4-7 Business Days
Published: Tor Books - March 30th, 2010

The first book in the John Cleaver series follows the titular sociopath John Cleaver as he tries to catch a serial killer. It is a dark and suspenseful book that goes in surprising directions. Cleaver's story starts as a simple thriller but as the main character goes down a dangerous rabbit hole, everything shifts to something unique and terrifying. Once it starts to grip you, it is very difficult to put down.

The Phantom Tollbooth By Norton Juster, Jules Feiffer (Illustrator) Cover Image
By Norton Juster, Jules Feiffer (Illustrator)
ISBN: 9780394820378
Availability: NOT ON OUR SHELVES. Usually Arrives in 4-7 Business Days
Published: Yearling - October 12th, 1988

The Phantom Tollbooth is a book full of magic and pure wonder. I read it for the first time as a child and I have been going back to it ever since. It has so much to say about the world and about life. As Milo journeys out of his apartment through the Phantom Tollbooth and into the Lands Beyond, he experiences a vibrant world that acts as a mirror to our own. This book is an absolute classic that everyone should read. 

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Mordew (Cities of the Weft #1) By Alex Pheby Cover Image
ISBN: 9781250817211
Availability: NOT ON OUR SHELVES. Usually Arrives in 4-7 Business Days
Published: Tor Books - September 14th, 2021

One of the highlights of Mordew is the strange and fascinating world in which the book takes place. Although it already starts out being dark and magical, everything transforms into something even more surreal as the plot advances. The protagonist, Nathan, thinks he understands how the world works at the start of the book but as he gets entangled with things that he cannot comprehend, the world he grew up in is suddenly unfamiliar and terrifying. 

The Shining By Stephen King Cover Image
ISBN: 9780345806789
Availability: NOT ON OUR SHELVES. Usually Arrives in 4-7 Business Days
Published: Anchor - August 27th, 2013

Jack Torrance and his small family move to the historic Overlook Hotel for Jack's job as the winter caretaker. Their stay at the Overlook begins a slow and gradual decline in sanity and rationality, and as supernatural phenomena start to take place everyone is put into danger. King is a master at building tension and it makes the buildup and climax of the book unforgettable. 

Dracula (Vintage Classics) By Bram Stoker Cover Image
ISBN: 9780307743305
Availability: NOT ON OUR SHELVES. Usually Arrives in 4-7 Business Days
Published: Vintage - June 14th, 2011

Told through letters and journal entries, you watch as the most infamous vampire wrecks havoc on the small English town of Whitby. Dracula stands out because the emphasis of the book is about how the main characters' worlds are turned upside down by the titular vampire. Their psychology, their rationality, and their fear are all played against each other by the unknown force of Dracula. Dracula is written in a way that makes you feel that you are descending down the rabbit hole along with the main characters, and it leaves quite an impression on you. 

Coraline By Neil Gaiman Cover Image
ISBN: 9780063088238
Availability: On Our Shelves Now
Published: William Morrow Paperbacks - September 21st, 2021

Reminiscent of Alice's Adventures in WonderlandCoraline also features a young protagonist who goes through a hole and winds up in a strange and interesting world. At first this Other World seems to be perfect and much better than boring reality, but it doesn't take long for Coraline to see what is really going on. This book is full of eerie fun and charm and it is something that will really stay with you.

Night Film: A Novel By Marisha Pessl Cover Image
ISBN: 9780812979787
Availability: On Our Shelves Now
Published: Random House Trade Paperbacks - July 1st, 2014

Night Film is about a journalist who is obsessed with a mystery and it is this obsession that takes him down the rabbit hole. This desire to know what really happened in the death of a young girl forces the main character to descend into a world that he does not understand and it changes his worldview permanently. The mystery in this book will leave you hooked and you will want to know the answers just as badly as the main character.

Annihilation: A Novel (The Southern Reach Trilogy #1) By Jeff VanderMeer Cover Image
ISBN: 9780374104092
Availability: On Our Shelves Now
Published: FSG Originals - February 4th, 2014

To me, there is no better rabbit hole story than VanderMeer's AnnihilationThe story follows a nameless biologist and her team as they explore the mysterious Area X, observing how it changes the natural landscape and how it changes them. It is tense, gripping, and beautifully written. The world of Area X seems so familiar and yet so disturbing at the same time. It is one of those books I wish I could read again for the first time. 

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