Many iconic books brilliantly capture the essence of cities and locations, providing readers with an immersive experience that transcends the boundaries of the classroom. As educators, we understand the significance of literature in shaping young minds, and we believe that by exploring the rich tapestry of cities through the lens of these novels, we can help students develop a deeper understanding of the world around them.
ThinkFives reviewed a selection of classic and contemporary works, each renowned for their vivid portrayal of the cities they are set in. Through these novels, we share the ways authors have masterfully depicted the culture, history, and spirit of various urban landscapes. We also provide excerpts and quotes from each book because as well as we think we write, only the author’s words can bring their stories to life.


To Kill a Mockingbird by Harper Lee
“To Kill a Mockingbird” is a classic and still on most high school reading lists. Set in the fictional town of Maycomb, Alabama, it serves as a microcosm of the South during the Great Depression. The novel captures the essence of the small town, weaving in details of its rich history, social structure, and deeply ingrained racial prejudices.
The sweltering heat, the slow pace of life, and the closeness of the community all contribute to the town’s atmosphere, evoking a palpable sense of time and place. Lee’s vivid descriptions of Maycomb’s landscape, the languid afternoons, and the buzzing gossip of the town’s inhabitants bring the setting to life and provide a realistic and immersive experience for the reader.
Quotes from the Novel:
- “Maycomb was an old town, but it was a tired old town when I first knew it… There was no hurry, for there was nowhere to go, nothing to buy and no money to buy it with, nothing to see outside the boundaries of Maycomb County.” (Chapter 1)
- “In rainy weather, the streets turned to red slop; grass grew on the sidewalks, the courthouse sagged in the square.” (Chapter 1)

The Great Gatsby by F. Scott Fitzgerald
“The Great Gatsby” is a quintessential portrayal of New York City during the Roaring Twenties, a time of excess, decadence, and ambition. You can almost feel your hair blowing in the air as Gatsby drives his yellow 1922 Rolls-Royce. The novel paints a vivid portrait of the city, contrasting the opulence of the wealthy in East and West Egg with the bleakness of the working class in the Valley of Ashes.

The vibrant parties, the luxurious mansions, and the bustling streets all capture the energy and excitement of the era. Fitzgerald also explores the darker side of the city, revealing the moral decay beneath the glittering surface. The novel’s evocative descriptions of New York City, the Jazz Age, and the American Dream create an unforgettable and immersive atmosphere that resonates with readers.
Quotes from the Novel:
- “I lived at West Egg, the – well, the less fashionable of the two, though this is a most superficial tag to express the bizarre and not a little sinister contrast between them.” (Chapter 1)
- “This is a valley of ashes – a fantastic farm where ashes grow like wheat into ridges and hills and grotesque gardens; where ashes take the forms of houses and chimneys and rising smoke, and, finally, with a transcendent effort, of men who move dimly and already crumbling through the powdery air.” (Chapter 2)


Moby-Dick by Herman Melville
Long before Jaws, Moby-Dick captured life in the whaling town of New Bedford, Massachusetts, which serves as the backdrop for the thrilling tale of Captain Ahab’s obsessive pursuit of the great white whale. The book captures the essence of the town’s seafaring culture, with vivid descriptions of the bustling waterfront, the imposing ships, and the hardworking sailors who risk their lives on the open sea.
The novel delves deep into the history and lore of whaling, immersing the reader in the gritty, dangerous world of the whaling industry. Melville’s richly detailed descriptions of New Bedford, its people, and the oceanic world create a fascinating and immersive experience for the reader.
Quotes from the Novel:
- “In New Bedford, fathers, they say, give whales for dowers to their daughters, and portion off their nieces with a few porpoises a-piece.” (Chapter 6)
- “The town itself is perhaps the dearest place to live in, in all New England. It is a land of oil, true enough: but not like Canaan; a land, also, of corn and wine.” (Chapter 6)

The Catcher in the Rye by J.D. Salinger
Still one of the top 5 books our teachers recommend to students, The Catcher in the Rye is set in New York City, specifically in the neighborhoods of the Upper East Side, Greenwich Village, and Central Park. The novel captures the essence of the city through the eyes of the protagonist, Holden Caulfield, as he wanders aimlessly through its streets, grappling with his disillusionment and feelings of alienation.

The sights and sounds of the bustling metropolis are brought to life by Salinger’s vivid descriptions, while the city’s darker side is also revealed through Holden’s encounters with loneliness, heartache, and hypocrisy. The novel’s portrayal of New York City evokes a visceral sense of the urban landscape and provides an intimate look at the challenges and complexities of navigating adolescence in the big city.
Quotes from the Novel:
- “New York’s terrible when somebody laughs on the street very late at night. You can hear it for miles. It makes you feel so lonesome and depressed.” (Chapter 8)
- “I live in New York, and I was thinking about the lagoon in Central Park, down near Central Park South. I was wondering if it would be frozen over when I got home, and if it was, where did the ducks go?” (Chapter 9)


Beloved by Toni Morrison
“Beloved” by Toni Morrison is set in Cincinnati, Ohio, and explores the city’s history of slavery and the Underground Railroad. The novel delves into the traumatic experiences of former slaves and their struggle to build new lives in a society that is still grappling with the legacy of slavery. Morrison’s richly detailed descriptions of Cincinnati and the surrounding countryside evoke a powerful sense of place, providing a vivid backdrop for the characters’ stories.
The novel also captures the unique atmosphere of the city, with its bustling riverfront, thriving African American community, and the tension between the past and the present. Through its exploration of Cincinnati’s history and the experiences of its residents, “Beloved” offers a compelling and immersive portrait of a city in transition.
Quotes from the Novel:
- “124 was spiteful. Full of a baby’s venom. The women in the house knew it, and so did the children… It was not a story to pass on.” (Chapter 1)
- “This is a place where they unloaded the Underground passengers and cleaned them up for the next station. A rest stop, you might say, between stations. But not a last stop, and not the first.” (Chapter 12)
What book captures a city of geography best for you?
Diana Gabaldon has done an amazing job of giving me images of Scotland as well as America during the revolutionary war. Great visual images! 😍 (My summer fictional reading!)
What a neat list to have- how books express the setting of a place! 📚👏❤️