A Literary Drinker's Guide to New York City
New York City has always been a place where writers drink and drinkers write. From the whiskey-soaked booths where O. Henry penned his masterpieces, to the dim back rooms where Kerouac and Ginsberg argued about God and jazz — the city's literary history is inseparable from its bars. And its bookstores are cathedrals.
This is your guide to both. A crawl through the neighborhoods, the shelves, and the stools where New York's greatest stories were told — or, at least, started.
567 Hudson St, New York, NY 10014
Established in 1880, it became a 1950s bohemian hub — most famous as the place where Welsh poet Dylan Thomas reportedly drank his final shots of whiskey before his death in 1953. James Baldwin, Jack Kerouac, and Norman Mailer were regulars. Kerouac was famously thrown out on several occasions, and reportedly found the words "Go home Jack" written in the men's room.
Dylan Thomas · Kerouac · Norman Mailer · James Baldwin
113 MacDougal St, New York, NY 10012
A favorite of the Lost Generation and the Beats. Hemingway, Ezra Pound, and E.E. Cummings were regulars. Legend says writer Joe Gould — subject of Joseph Mitchell's Joe Gould's Secret — lived out of the booths and received his mail here.
Hemingway · Ezra Pound · E.E. Cummings
59 Christopher St, New York, NY 10014
The epicenter of the Beat Generation. Jack Kerouac was famously photographed here, and it served as a meeting ground for Allen Ginsberg and a young Bob Dylan, who found his voice in these smoky rooms before becoming a legend.
Jack Kerouac · Allen Ginsberg · Bob Dylan
154 W 10th St, New York, NY 10014
Named after the Gertrude Stein novel, this beloved corner bookstore is a sanctuary for local writers and publishing professionals. Known for its curated selection and irreplaceable old New York literary atmosphere — a place where books are still chosen with genuine care.
Named after Gertrude Stein · Est. 1968
15 E 7th St, New York, NY 10003
Opened in 1854, one of the city's oldest bars. Immortalized by Joseph Mitchell in his legendary New Yorker profiles. E.E. Cummings was a frequent patron — he wrote "i was sitting in mcsorley's" in 1923. The bar famously didn't admit women until 1970.
E.E. Cummings · Joseph Mitchell · Est. 1854
85 E 4th St, New York, NY 10003
Located in a former Ukrainian social club, this dim Soviet-themed bar is the modern heartbeat of the NYC literary scene. Its KGB Reading Series has hosted Pulitzer winners and debut novelists alike — the city's finest place to hear fiction read aloud.
KGB Reading Series · Still active today
129 E 18th St, New York, NY 10003
A Gramercy landmark since 1864. O. Henry famously wrote "The Gift of the Magi" in the front booth — the bar appears in his stories under the name "Healy's." Ludwig Bemelmans also wrote the first Madeline book here, reportedly on the back of a menu.
O. Henry · Ludwig Bemelmans · Est. 1864
828 Broadway, New York, NY 10003
Famed for its "18 miles of books," this is the undisputed king of NYC bookstores. Since 1927 it has been the primary source for used, rare, and new titles for the city's intellectual elite. To visit New York without visiting the Strand is to have missed the point.
18 Miles of Books · Est. 1927
59 W 44th St, New York, NY 10036
Home to the Algonquin Round Table of the 1920s — Dorothy Parker, Robert Benchley, and George S. Kaufman met here daily. Harold Ross won so much money from fellow members in a poker game that he used it to found The New Yorker magazine.
Dorothy Parker · The New Yorker · Round Table
35 E 76th St, New York, NY 10021
Named after Ludwig Bemelmans, author and illustrator of the Madeline children's books. He painted the whimsical Central Park murals that cover all four walls — in exchange for room and board at the hotel. One of New York's most cherished secrets.
Ludwig Bemelmans · Madeline · Original murals
116 E 59th St, New York, NY 10022
Established in 1925 and still family-owned, this six-story townhouse specializes in antiquarian books, rare maps, and autographs. A genuine time capsule of the city's scholarly history — hiding in plain sight since the Jazz Age.
Antiquarian · Rare Maps · Est. 1925
266 W 39th St, New York, NY 10018
A hundred-year-old institution for playwrights and theater lovers. Famously saved from closing by Lin-Manuel Miranda, it remains the primary resource for scripts and theatrical literature in the city — and one of Broadway's most beloved gathering places.
Saved by Lin-Manuel Miranda · Scripts & Theater
45 W 27th St, New York, NY 10001
A grand homage to the Irish writer, poet, and playwright whose wit remains unmatched. Beyond paying tribute to the man who once said "I have the simplest tastes — I am always satisfied with the best," the bar claims a remarkable physical distinction: at 118.5 feet, it is home to New York City's longest bar. The Victorian opulence — gilded ceilings, velvet, and portraits of the great man himself — feels entirely appropriate.
Homage to Oscar Wilde · NYC's Longest Bar — 118.5 ft
45 E 18th St, New York, NY 10003
Dating to 1892 with its original pressed-tin ceilings, mahogany bar, and tile floors still intact, Old Town is what Pulitzer Prize-winning author Frank McCourt — of Angela's Ashes — called "the king of New York bars — where you can still talk." Nobel Prize-winning poet Seamus Heaney considered it his favorite bar in the city and visited whenever he was in town. Signed book jackets from McCourt, Billy Collins, Nick Hornby, and Christopher Hitchens line the walls. Andy Warhol was once a regular too.
Frank McCourt · Seamus Heaney · Billy Collins · Est. 1892
180 Orchard St, New York, NY 10002
The largest independent bookstore on the Lower East Side, named after owner Bradley Tusk's grandfather's menswear shop that stood around the corner on Allen Street since 1952. A genuine community institution: 10,000+ hand-curated titles, an amphitheater-style event space for 85, a full cafe, and a state-of-the-art podcast studio facing the street — free and open to the public to use. One of the most inventive bookstore spaces built in New York in a generation.
Free Podcast Studio · 10,000+ Titles · LES Institution · Est. 2022
1133 Broadway, New York, NY 10010
One of New York's most beautiful bookstores, established in 1964 on Fifth Avenue and now in a stunning NoMad location. Specializing in illustrated books on architecture, interior design, fashion, photography, and the fine arts, as well as literature and foreign language titles. Cast iron chandeliers, ornately decorated vaulting, and regular author events make it a destination for distinguished book lovers from around the world.
Est. 1964 · Art & Architecture · Cast Iron Chandeliers
If Manhattan's literary bars are about history — the booths where the great ones drank — Brooklyn's are about what's happening right now. The borough has become the true center of New York's working literary community: the writers who live here, the reading series that shape what gets published, and the bookstores that are genuinely part of their neighborhoods.
702 Union St, Brooklyn, NY 11215
A converted warehouse that feels like a cozy, oversized Victorian library — complete with a stone fireplace, floor-to-ceiling bookshelves, and leather armchairs. A favorite afternoon writing spot for Park Slope's literary community. The basement venue regularly hosts literary-minded comedy and storytelling shows that draw Brooklyn's best writers as both audience and performers.
Storytelling & Literary Comedy · Victorian Library Aesthetic
15 Lafayette Ave, Brooklyn, NY 11217
A dedicated home for the art of storytelling. The library and bookstore are open to all, but the real draw is the second-floor Cafe & Bar — open to the public and serving literary-themed cocktails in a space literally surrounded by books. One of the few places in New York where you can have a drink, attend a reading, and buy a novel all under one roof.
Literary Cocktails · Readings & Events · Library Bar
686 Fulton St, Brooklyn, NY 11217
Fort Greene's beloved independent bookstore, founded in 2009 after owner Jessica Stockton-Bagnulo won a $15,000 grand prize from the Brooklyn Public Library for her business plan. A community institution that hosts the Brooklyn Voices and BAM Unbound literary series, with past events featuring Ta-Nehisi Coates, Junot Díaz, Jhumpa Lahiri, Neil Gaiman, and Zadie Smith. The gold standard for what a neighborhood bookstore should be.
Ta-Nehisi Coates · Neil Gaiman · Zadie Smith · Est. 2009
253 Conover St, Brooklyn, NY 11231
A Red Hook legend since the 1890s. This waterfront saloon is a ramshackle sanctuary for the old Brooklyn creative class — writers, painters, and musicians drawn by its end-of-the-world atmosphere on the harbor's edge. Its late owner Sunny Balzano was a philosopher and artist who made the bar a beacon for anyone making things that didn't fit anywhere else.
Est. 1890s · Old Brooklyn Creative Class · Waterfront
618 St Johns Pl, Brooklyn, NY 11238
While it's a great beer garden in its own right, Franklin Park is world-renowned in literary circles for the Franklin Park Reading Series — one of the most important contemporary reading series in the country. It has hosted Colson Whitehead, Jennifer Egan, and dozens of the writers who define American fiction today, making it a critical hub for Brooklyn's living literary community.
Franklin Park Reading Series · Colson Whitehead · Jennifer Egan
339 Macon St, Brooklyn, NY 11216
One of the most anticipated literary openings in New York in years. Co-founded by Pulitzer Prize-winning journalist Nikole Hannah-Jones — creator of The 1619 Project — this space is modeled after the literary salons of the Harlem Renaissance, with an Art Deco aesthetic and a mission to celebrate Black literature and intellectual exchange. Micro-residency apartments upstairs host visiting writers. Opening 2026.
Nikole Hannah-Jones · The 1619 Project · Opening 2026
770 Hart St, Brooklyn, NY 11237
A cozy used bookstore that stays open late and serves coffee, beer, and wine alongside its shelves — a rare combination that draws Bushwick's younger writing community long after other shops have closed. Pioneered the beloved "books-for-bar-tab" trade-in system: bring in a stack of used books, drink for free. Low-key, unpretentious, and exactly what a neighborhood bookstore should be.
Books-for-Bar-Tab · Late Night · Used Books + Beer
306 Grand St, Brooklyn, NY 11211
New York City's first bookstore dedicated exclusively to horror and dark literature, opened in September 2025 after a wildly successful Kickstarter campaign. A permanent brick-and-mortar location featuring a full espresso cafe with Devoción coffee and a beer and wine bar. The interior goes full dark academia — plush black armchairs, carved shelves in dark-washed wood, chandeliers, and a stamped-tin ceiling. Shelves are organized by horror subgenre: Haunted Houses, Cosmic, Creature Corner. There's a graveyard in the back courtyard.
NYC's First Horror Bookstore · Beer & Wine · Est. 2025
The only bookstore in New York dedicated exclusively to romance novels — from classic love stories to queer romance, historical fiction, and fantasy. Woman- and queer-owned, the Park Slope store features a diverse selection of romance fiction and hosts author talks, book clubs, and events. A joyful, unapologetic celebration of a genre that outsells literary fiction every year — and a genuinely beloved neighborhood institution.
Romance-Only · Woman & Queer Owned · Author Events
126 Franklin St, Brooklyn, NY 11222
An independent community bookstore since 2007, with locations in Greenpoint, Brooklyn and Jersey City. Small but mighty — specializing in literary fiction, nonfiction, and children's books, with a basement event space that has hosted Murakami midnight parties, Bananagrams tournaments, and readings by Jonathan Lethem and Alice Munro. A true neighborhood anchor in Greenpoint's creative community.
Est. 2007 · Literary Fiction · Greenpoint Institution
94 Bedford Ave, Brooklyn, NY 11211
More dive bar than library, but a storied Williamsburg haunt for writers who prefer grit over glamour. In the era before the neighborhood was discovered, this was where the creative class drank cheaply and argued loudly. It has appeared in novels and essays as a symbol of the neighborhood's pre-gentrification soul — a reminder of the Brooklyn that made the writers who later made Brooklyn famous.
Pre-Gentrification Williamsburg · Writers' Dive · Bedford Ave
William Shakespeare was born in Stratford-upon-Avon, England, in April 1564. The exact date of his birth is not recorded, but it is most often celebrated around the world on April 23rd — the same day, centuries later, that New Yorkers gathered to raise a glass in his name.
On that day (or really, any day), celebrate New York City's literary and drinking traditions by supporting local bookstores, spending time in bars with a literary impact, and being with — and making — new friends.
✦ All bookstores and literary bars featured in this guide · bookstorebarcrawl.com
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