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Winter is upon us in 2019 and New York City is getting atmospheric, 70 years ago to Holden Caulfield, it seemed like the perfect place to wallow. In December 1949, Holden Caulfield flunked out of another boarding school. Instead of seeing out the last few days before heading home to face his parents, Holden jumped on a train to New York and wandered Manhattan in a haze of angst and awkwardness.

While J. D. Salinger’s The Catcher in the Rye changed the game for American literature. New York City and all its gritty and glorious bustle changed the game for Holden. Follow in his footsteps through the city and see what kind of angsty adventure awaits you.

Pennsylvania Station

The Penn Station Holden Caulfield found when he arrived is completely different to the Penn Station that greets travelers today. It was demolished and redeveloped in the mid-1960s, but some architectural remnants are scattered throughout (and occasionally visitors can book tours to see them).

Holden Caulfield, a New York native, held little fascination for Penn Station. He breezes through, ducks into a phone booth, then hails a cab and heads north. You can do the same if this is how you arrived in the city.

The Edmont Hotel, Ernie’s Bar (fictional)

Holden checks into a “very crumby” hotel, tries to pick up some women in the bar, visits a Greenwich Village nightclub, then walks 41 blocks back to the hotel.

The Edmont Hotel and Ernie’s Bar are (perhaps thankfully) fictional, but in A Reader’s Companion to J. D. Salinger’s The Catcher in the Rye Peter G. Beidler estimates their location. The Edmont was likely on West 57th Street between Sixth and Seventh Avenues. You should make like Holden and find a club or bar in the Village for an evening. We like Employees Only. It's a far cry from Holden's dive, but the cocktails are world-class.

Grand Central Terminal

The next morning Holden jumps in a taxi to “Grand Central Station”, stores his bags, and eats a huge breakfast.

While Grand Central Terminal no longer offers luggage storage, the Dining Concourse, Great Northern Food Hall and Grand Central Oyster Bar & Restaurant are great places to eat (and maybe even find Holden’s breakfast of orange juice, bacon and eggs, toast and coffee).

Related article: NYC's best food halls

Broadway

After breakfast Holden walks through a “mobbed and messy” Broadway and buys theatre tickets for a date that afternoon. Then he takes a cab up to the park. You should definitely do the same. The TKTS booth in Times Square sells half-price same tickets to selected shows and musicals, it is so much fun to just go and see what you can get.

The American Museum of Natural History

Holden heads to the Mall at Central Park to look for his younger sister Phoebe, then walks to the American Museum of Natural History. Despite recalling happy memories of class trips there as a child, Holden doesn’t go inside as it means acknowledging just how much he has changed.

Don’t make the same mistake Holden did: the American Museum of Natural history has over 34 million artifacts (including the same Great Canoe from Holden’s memory) and is the largest natural history museum in the world.

Rockefeller Center Skating Rink

After waiting for his date at the now shuttered Biltmore hotel, Holden takes the girl to a show. Afterwards Holden’s date enthusiastically suggests going ice skating at the Rockefeller Center Skating Rink. She wanted to go ice skating, but she also wanted to wear one of the dresses they loaned out in the 1940s. Open mid-October to April, a skate on the ice at the Rockefeller Center is one of the most celebrated New York winter experiences.

Radio City Music Hall

Once his date leaves, Holden sees a movie at Radio City Music Hall. He arrives during the live stage show which preceded all films in the 1940s and sees The Rockettes (famed precision dance performers), as well as "The Living Nativity".

While Radio City now primarily hosts concerts, from early November to the new year visitors can enjoy its Christmas Spectacular which features both a number by The Rockettes and the same nativity production that has ran since 1931.

Central Park – Pond

Just after Holden meets an old classmate at the fictional Wicker Bar inside the Seton Hotel on 54th Street, he visits The Pond on the south side of Central Park which he refers to as the lagoon: certainly real, and certainly the most iconic landmark in the book.

Holden spends much of the novel fixated on where the ducks go during winter: daydreaming about it during a lecture from his teacher, asking cab drivers about it, and even visiting the lagoon late at night to investigate. In the present day, “The Pond” still offers visitors a serene place to sit and relax (with plenty of ducks to watch).

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Metropolitan Museum of Art

Later in the novel, Holden visits the Metropolitan Museum of Art. His intention is to meet his sister Phoebe but he’s distracted by two young children who are intent on seeing the Egyptian mummies, part of the impressive ancient Egyptian collection that is still housed at the museum today.

In fact, The Met houses the largest and most important collection of art and antiquities in the world and visitors should plan on spending several hours exploring the 17-acre exhibition space.

Related article: Spend the perfect weekend

Central Park Zoo and Carousel

Phoebe becomes frustrated and runs away, so Holden follows her across the street to Central Park, then down into the zoo, and through a tunnel out to where the is. He insists on buying Phoebe a ticket to ride the carousel and, mesmerized, she agrees.

The Central Park Zoo is a small but the feeding times for the sea lions and penguins are popular attractions. The carousel is one of the few remaining hand-carved merry-go-rounds in the country and is also one of the largest featuring 57 magical horses and two chariots.

Soon after Phoebe boards the carousel it begins to rain, and The Catcher in the Rye comes to its emotional finale as Holden watches Phoebe ride:

“I felt so damn happy all of sudden, the way old Phoebe kept going around and around. I was damn near bawling, I felt so damn happy... God, I wish you could've been there.”