New York City Skyline
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For a city of nearly 8.5 million, New Yorkers certainly have a knack for preserving and honoring each other’s stories.

As the city continues to evolve, with new skyscrapers and highbrow art scenes emerging in Brooklyn and Queens, the city’s rich past is more relevant than ever. For your next trip to the Big Apple, here are eight points of interest that are worth visiting to get a better grasp of New York City’s many cultural layers.

Brooklyn Bridge

Spanning from the Financial District in lower Manhattan all the way to Brooklyn’s charming DUMBO neighborhood, the iconic Brooklyn Bridge inspires awe with its gigantic limestone and granite towers. It’s also a fantastic way to spend a sunny day in the city—just make sure you stay out of the bike lane.

Lombardi's Pizza
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Over on Spring Street, right in the heart of Nolita, you’ll find Lombardi’s, recognized as America’s first pizzeria. (There’s even a plaque on the door proclaiming it.) Except for a 10-year hiatus in the 1980s when the restaurant changed ownership, Lombardi's has been doling out its signature coal-fired pies since 1905 — so there’s been plenty of time to perfect the technique.

The Strand

Another treasured piece of New York City real estate, The Strand’s tagline is “18 miles of books,” as in the distance that could be covered if every book in the store were placed end to end. Maybe it's true and maybe it isn't, but with thousands of titles spanning four levels, plus a sizeable $1 bargain rack outside, it’s impossible to walk out without at least one interesting find.

Washington Square Park

A five-minute walk from Union Square, this lovely tree-lined park is an easy halfway point for tourists making their way from the East Village to the West Village, or vice versa. In a way, Washington Square functions like a microcosm of wider New York. There are old-timers reading the newspaper on picnic benches, dancers and musicians who make their stage each night under the brightly lit Arch, and chess tables near the park’s west entrance—in short, a little something for everyone.

Shakespeare in the Park

Now in its 55th year, this free seasonal theatrical production takes place in the Delacorte Theater, a 1,800-seat open-air theater in Central Park.

Getting tickets to the iconic summer tradition requires a little bit of legwork: You’ll need to line up early the morning of the performance (shows only run during the summer, from May to August), or enter the digital lottery. But with a setting this unique, the show is worth the wait.

Morris Jumel Mansion

To get to Manhattan’s oldest house, you’ll need to head uptown. Ride the C train to 163rd Street, then walk two blocks to the east. Upon entering the 252-year-old estate, which is set among beautiful gardens, the first thing you’ll notice is the altitude: the house was originally built on Mount Morris, one of the highest points in the city. Later, during the jazz era of the 1920s and 1930s, this area came to be known as Sugar Hill.

New York City's High Line Park
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High Line

Speaking of altitude, you’ll certainly get a rise from walking down the High Line, New York City’s first elevated park. Built on old railroad tracks that hover thirty feet above traffic, the spectacularly landscaped gardens are a colorful treat as you wind your way south from 34th Street all the way down to the Whitney Museum of American Art.

Village Vanguard

An indispensable (and some would say seminal) part of the New York jazz scene, this legendary venue got its start in the 1930s, when it would host weekly jam sessions with a 50 cent cover. Decades later, after greats like Miles Davis, Lester Young, Bill Evans, Stan Getz have all left their mark here, the stage continues to draw top international talent, and is a reliably fun way to spend an evening out in the city.