New York's Most Fascinating Walking Tours

Explore New York with a walking tour
Explore New York with a walking tour | © RBS / Alamy Stock Photo
Photo of Esme Benjamin
Wellness Editor27 September 2019

New York’s grid of streets, distinctive neighborhoods, world-famous sights and rich history make it an ideal place for a walking tour. Here are some of the best guided walking tours the city has to offer.

Observe the evolution of street art with Graff Tours

Historical Landmark
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Street Art in Bushwick, Brooklyn. New York, USA. All art by The Bushwick Collective.
Learn more about street art with a walking tour through the Lower East Side and Brooklyn | © Anthony Wallbank / Alamy Stock Photo

Although street art is a worldwide phenomenon, there’s no better place to get a graffiti tour than New York – birthplace of the outlaw art form. Join Graff Tours’ knowledgeable guides (all artists themselves) on a trip through some of the city’s most graffiti-covered neighborhoods: the Lower East Side and Bushwick. You’ll learn about street art’s evolution, from illegal tagging and wheatpasting (slapping paper to walls and lampposts using a sticky flour and water mixture) to sponsored, elaborate murals. You can even test your own ‘can control’ with a spray-painting lesson.

Embrace immigration at the Tenement Museum

Museum, Library, Building
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Tenement Museum in the Lower East Side of New York City, NY, USA.
The Tenement Museum on the Lower East Side explores the story of immigration in the USA | © Paule Saviano / Alamy Stock Photo
The Tenement Museum’s walking tours take you on a journey through the Lower East Side, a neighborhood shaped by a convergence of immigrant cultures. This tour stops at seemingly insignificant places to reveal hidden stories, helping attendees understand the neighborhood’s history while engaging with its present. Make sure you explore the museum’s two tenement buildings at 97 and 103 Orchard Street to get a deeper perspective of their past residents and what it was like to live there all those years ago.

Drink like America's great writers on a Literary Pub Crawl

Historical Landmark, Theater
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The White Horse Tavern, New York City
The White Horse Tavern was popular with literary figures of the '50s and '60s such as Dylan Thomas | © Carl DeAbreu / Alamy Stock Photo

Join the self-described “pre-eminent drunken gurus of Village lore” on a bookish tour of Greenwich Village. The Literary Pub Crawl visits the previous homes and favorite watering holes of America’s most celebrated writers, including Dylan Thomas, Allen Ginsburg, Emma Lazarus, Edna St. Vincent Millay, Jack Kerouac, Edgar Allen Poe and Mark Twain. The success of the company’s flagship tour of the Village, which started in 1998, has spawned similar offerings in Brooklyn, Times Square and on the High Line.

Learn the history of NYC's criminal underbelly

Historical Landmark
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Little Italy Sign at Mulberry Street intersection with Broome Street, Nolita, Manhattan, New York City
The Rise and Fall of the American Mafia walking tour will take you through Little Italy | © John Rice / Alamy Stock Photo

On this two-hour tour, get insight into the organized crime syndicates who controlled New York from the start of the 20th century. There are three tours to choose from: The Rise and Fall of the American Mafia, which takes you on an after-dark trip through Little Italy and the East Village; the Little Italy and Chinatown Gangsters Walking Tour, which covers the gangs of Mulberry Street from the 1840s through the 1920s; and Jewish Gangsters of the Lower East Side Tour, which tells the tale of the tenement gangsters known as “Kosher Nostra.”

See New York through a photographer's eyes

Historical Landmark
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Times Square In Late Afternoon, Manhattan, New York, USA
Have your photograph taken at the iconic Times Square | © jejim120 / Alamy Stock Photo

When you book a PhotoTrek tour, you get a guide and a personal photographer in one. Explore the city, picking up local recommendations for things to see and dishes to eat along the way, while your guide directs impromptu photo shoots of your group. You’ll finish up the day with plenty of Instagram content and the stories attached to New York’s most recognizable landmarks. The guides will also teach you how to master the subway, so you can navigate the city like a local.

Discover hidden attractions with the New York Adventure Club

Historical Landmark
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The New York Adventure Club unlocks little-known attractions across the city. While many of its offerings are confined to one location (think a matcha ceremony in a secret Japanese tea garden or a lesson with an urban beekeeper), many of the unusual itineraries involve plenty of walking. You can explore the abandoned Ellis Island hospital complex, take in the sights of City Island, the Bronx (aka the “Cape Cod of New York”), or soak up elevated views of Manhattan from the secret rooftop farms and wineries at Brooklyn Navy Yards.

Hit the shops with a Brooklyn fashion designer

Historical Landmark
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The Brooklyn Food and Fashion Tour is perfect for those who want to return home with apparel that’s a little more unique that an ‘I heart NY’ T-shirt. It’s hosted by a fashion and textile designer who’s also trained as a personal shopper (hello, industry discounts!). The tour stops at boutique clothing stores in Williamsburg, one of Brooklyn’s trendiest neighborhoods, as well as a handful of food spots to keep you fueled for the four-hour shopping spree.

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