Inside the Apple: A Streetwise History of New York City by Michelle Nevius and James Nevius
If you’re keen to get a stronger sense of New York City history than a typical travel guide offers, you’ll want this indispensable book in your pocket. Moving chronologically from the New Amsterdam days, the short and sweet chapters pull up key stories from the city’s past, tales you won’t always find in more visitor-friendly tomes. The book includes 14 walking tour routes, but the clear layout makes it easy to pick and mix your own.
The Group by Mary McCarthy
Depression-era New York is the backdrop as McCarthy masterfully weaves together the stories of nine women building lives for themselves after college. They experience workplace sexism, struggle to get birth control, and ... douching. As Candace Bushnell said, "The Group reminds us that not much has really changed".
Re Jane by Patricia Park
In this modern adaptation of Charlotte Brontë’s classic novel, Jane’s trying to escape her strict Korean upbringing in Queens, and salvation (her Thornfield Hall, if you will) is a Brooklyn family seeking an au pair. The "madwoman in the attic" is her boss — a women’s studies professor stressing over securing tenure. Jane's search for independence and belonging is set against a background of a city in flux that is taking in 9/11 and its aftermath, and the gradual creep of gentrification.
The Age of Innocence by Edith Wharton
Take a trip to Old New York, where Newland Archer’s romantic dilemma is the centerpiece of a dissection of the ritual, pettiness, and hypocrisy of the New York elite. The city itself is changing before the characters’ eyes; the characters' concerns over keeping company with the "right sort of people" and the battle of old and new money are as familiar today as ever. It’s basically a Gilded Age Gossip Girl.
Gossip Girl by Cecily von Ziegesar
Speaking of which, what’s a trip to the Big Apple without a dip into the scandalous lives of Manhattan’s modern-day elite? Get your headband on and go browse the Three Bs (Barney’s, Bendel’s, and Bergdorf’s), and of course a snack stop on the Met steps is mandatory — just don’t sit higher than Queen B...
The Bell Jar by Sylvia Plath
Many come to New York in search of a dream. In The Bell Jar, the glamour and promise of city life quickly melts into depression in this different take on taking Manhattan. You can even read the novel against Plath’s diaries of her own time in New York to see how fact informed fiction. (The Barbizon Hotel where she stayed in 1953 still stands, but has since been turned into condos.)
Brooklyn by Colm Tóibín
Also set in the '50s, Brooklyn tells the story of Eilis, another woman who has come to mid-century New York for a better job and life. Not only is she alone in a strange city, but after a tragedy back in Ireland, she finds herself torn between her old and new lives, and must decide where her future lies. We walk alongside her through a Brooklyn full of opportunity, but tensions between the different communities are clear.
Breakfast at Tiffany's by Truman Capote
The legendary tale that made Audrey Hepburn an icon (and launched a million obsessions with those blue boxes), is even better in book form. Our protagonist Holly comes across a little less carefree here; she’s a thoroughly perplexing heroine whose "true story" you can never be sure of. New York has given her a chance to reinvent herself — but what’s her real story? The male-gaziness of the narrative is a little frustrating, but it’s a short, entertaining read.
Passing by Nella Larsen
Irene’s comfortable life in '20s Harlem is disrupted by the return of Claire, who she hasn’t seen for years. Irene has always been fascinated by her old acquaintance, especially because she passes as white. This makes Claire a particularly controversial figure among her old friends — especially once they’ve met her racist husband. There are heavy sexual undertones to Claire and Irene’s relationship, and "passing" also becomes about passing as straight.
Just Kids by Patti Smith
Smith’s hypnotic prose draws us along with her through New York City during some of its most exciting decades for art and music. It’s a haunting work, and a compelling love letter to the city and those who travelled through it with her — especially Robert Mapplethorpe.
The Triangle Shirtwaist Factory Fire by Charles River Editors
Manhattan wasn’t always shiny skyscrapers and white collar workers. This short volume reveals the area's industrial past, when factories dominated. First-hand testimony illuminates the shocking circumstances that led to the tragic Triangle Shirtwaist Factory fire — a somewhat gruesome, but necessary, reminder of the city’s industrial heritage.
The Great Gatsby by F. Scott Fitzgerald
That yellow car. That Plaza suite. The whole damn Jazz Age. Loud, fast, and achingly tragic, this is the quintessential New York novel, taking in the "steady golden roar" of a city at its peak. Make sure you read it before taking Manhattan, and maybe even stop off at a few of Nick and co's choice landmarks. If you’ve already read the novel to death, Fitzgerald’s essay, My Lost City, is also riddled with equal parts contagious romanticism and soaring nostalgia — enough to fuel any journey around the metropolis.