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It Happened in NYC
NY Gangsters Tour (Photo: NY Gangsters Tour)

7 Shocking Tours of New York City

Get the skinny on the city you thought you knew with tours that explore everything from mafia lore to the most recent and salacious celebrity misbehaviors, plus ghost-hunting tours that even the Ghostbusters would appreciate

Ah, New York. The stunning skyline. Romantic walks through Central Park. Elegant restaurants. And grisly murders. Did we get your attention? Yes, before the Big Apple became one of the safest big cities in the nation, there were centuries of shocking events whose truths and ghosts will lead the bravest of New Yorkers down the dark rabbit hole of history (and likely have you looking over your shoulder). Read on for seven of the most shocking NYC tours … if you dare.


Boroughs of the Dead's Murder, Scandal and Vice tour

Boroughs of the Dead’s Murder, Scandal, and Vice tour features history on sordid establishments like McGurk’s Suicide Hall where many ladies of the night frequented (Photo: Courtesy of Boroughs of the Dead)

Boroughs of the Dead – Murder, Scandal and Vice
If you’re looking for the dark side of New York, and we mean really dark, this is the tour for you. Conducted by real-life horror author Andrea Janes, the tour will completely immerse you in the terrifying tales of life on the rough streets of 19th century New York. The tour touches on scandalous stories, such as the dirty history of McGurk’s Suicide Hall that was one of the city’s most infamous dive bars along the Bowery, and horrible crimes that remain unsolved today. Other options led by Janes include the Dark Histories of Lower Manhattan tour that dives into horrific stories from New York’s colonial past and leads you through historic graveyards and taverns. It consists of 25 percent riots, rebellions and war, 35 percent torture and executions, and 40 percent weird, according to Janes, and the statistics speak for themselves. Throughout the year there are also seasonal tales like the Ghosts of Christmas Past tour that includes creepy stories with a holiday twist and a visit to a haunted and historic Victorian mansion.

DETAILS: Schedules vary; most tours are $20 pp in advance, $25 at the door (get tickets!); south end of City Hall Park by the fountain;


Mulberry Street NYC ca. 1900, part of the original Five Points

Mulberry Street NYC ca. 1900, part of the original Five Points (Photo: Detroit Publishing Company/Library of Congress Prints and Photographs Division Washington, D.C. 20540 USA)

The “Official” Gangs of New York Tour
You could just stay home and watch Scorsese’s entertaining movie Gangs of New York, but what fun is that when you can brave a day on the actual streets where it all took place? A stroll through the famous Five Points neighborhood today is tame, but it was once one of the most dangerous places on earth. Big Onion Walking Tours is known for employing experts in the field of New York history — including knowledgeable academics — so you’ll get all the juicy details on how this neighborhood became the most notorious in the city. Learn how out-of-control gangs controlled the local economy and used terror to keep power on the chaotic streets of New York. This is not a sanitized version either; expect the guides to touch on mature themes. You’ll encounter “Murderer’s Alley” that used to be lined with opium dens, learn the history of the African Burial Ground that was rediscovered in 1991, and gain insight into the origins of the explosive Draft Riots of 1863 that changed the city forever. The best part is: You don’t have to pay in advance. Check the online schedule and just show up at the meeting point with $20, and you’re ready for an adventure.

DETAILS: Schedules vary; $20 pp; the southeast corner of Broadway & Chambers Street, at the edge of City Hall Park;


Ghosts of New York

Guide Jamie Owens points out a possible ghost of the East Village in front of St. Mark’s Church in the Bowery (Photo: Courtesy of Ghosts of New York)

Ghosts of New York
If you thought only a few places in Manhattan were haunted, guess again. Almost every block of the island holds spooky mysteries that are just waiting to be uncovered, and this outfit has more than 14 tours from which to choose. Explore the tragic haunts of John Lennon on the Upper West Side or join the ghost of Peter Stuyvesant as you mingle with the likes of Washington Irving and Edgar Allan Poe in the East Village. We’re not joking when we say tour guides really get into the spirit during the tours. They have even been known to perform exorcisms at times, including one to lift the curse that (supposedly) prevents New York City mayors from moving on to higher offices. Check back in to see if new mayor Bill de Blasio climbs the political ladder. For something more relaxed, there are two pub crawls where you can grab a pint as you explore the old hangouts of Dylan Thomas and learn about the dark side of magician Harry Houdini in some of his favorite watering holes. The ghosts of New York will surely be smiling down on you as you raise a glass to them.

DETAILS: Sat. 7:30pm; $20-$25 pp; 85 W. 3rd St.;


NY Gangsters Tour

NY Gangsters Tour gets down and dirty in Little Italy with tales of the mob and more (Photo: NY Gangsters Tour)

NY Gangsters Tour
Unlike the Gangs of New York tour that takes you back a few hundred years, the NYC Gangster Tour brings you to a more recent but no less scarier time in New York. Get an inside look under the ugly truths of organized crime syndicates that have controlled New York since the first settlers and immigrants arrived on its shores. From the Tongs of Chinatown and the Irish Westies to the Russian Mob and the grandaddy of them all — the Mafia — tour-goers get a no-nonsense view of the places in Little Italy, Chinatown and the Lower East Side where really bad stuff went down including plenty of innocent (and sometimes not so innocent) bystanders getting whacked. The Italians aren’t the only act in town, however, there’s also a Jewish Gangsters of the Lower East Side tour that chronicles how corrupt groups controlled one of New York’s most famous neighborhoods through contract killings and gambling rings.

DETAILS: Thu.-Sun.; $25-$35 pp; corner of Mulberry and Worth streets and 168 1st Ave. near E. 10th St.;


Grand Central Terminal

Explore the haunted corners of NYC’s landmarks like Grand Central Terminal on the Ghost Doctors tour (Photo: Martine266/Flickr CC)

Hunting Spirits with the Ghost Doctors
Who you gonna call? Admit it, when you were a kid you probably wanted to join Bill Murray, Dan Akroyd and Ivan Reitman as a member of the Ghostbusters. You’d get to live in a firehouse, research paranormal activity, and seek out ghosts on the exciting streets of New York whenever the call comes in. Well, that might be just a dream, but you can live out your fantasy with a gang of pros who wander landmarks like Central Park, Grand Central Terminal and the Metropolitan Museum of Arton the lookout for spirits. This is not your average afternoon tour with some interesting facts and a relaxing bus ride. This is an interactive experience where your guides lead you on a hunt for spooky ghosts while tapping into the paranormal energy of the city. Dr. Pete and Dr. Stew are licensed tour guides and have spent decades uncovering secret supernatural hideaways that lurk in the night. Tours rotate among attractions such as the South Street Seaport and Flushing Meadows. Come ready to participate in this night of supernatural activity where you might just uncover something strange.

DETAILS: Schedules vary; $30 pp; for all tour info call 347-502-7352 or email;


Circa 1886, Looking west across 5th Avenue and 54th at 684 Fifth Avenue

Circa 1886, Looking west across 5th Avenue and 54th at 684 Fifth Avenue, which was built as wedding gift of William H. Vanderbilt for his daughter Florence and her husband Hamilton Twombly. The other mansion (left) at 680 was the home of William Seward Webb and Vanderbilt’s other daughter Eliza. (Photo: Albert Levy/Wikimedia CC)

Crimes of the Fifth Avenue Gold Coast
Dreams of American wealth and prosperity collide with the dark side of power and corruption along one of the world’s most storied stretches — Fifth Avenue on the Upper East Side. Tours of the area are led by Joyce Gold, a teacher of Manhattan history at New York University, who has been sharing her deep knowledge of local lore for more than 25 years. Many of the mansions and gilded towers that look beautiful on the outside contain terrible secrets once you get past the front door. Learn about the richest (and some of the creepiest) men in America who gathered private armies, tried to conceal criminal acts, and were guilty of financial wrongdoing that would make today’s Bernie Madoff knockoffs look tame. And speaking of Mr. Madoff, you’ll also walk by his former residence that attracted throngs of media just a few years ago, along with the fancy homes of ex-Governor Eliot Spitzer, Martha Stewart, and Klaus and Sunny von Bulow.

DETAILS: Schedules vary; $20 pp; tour starts at The Frick Collection, 1 E. 70th St.;


TMZ Tour

(Photo: Courtesy of TMZ)

TMZ Celebrity Scandal Tour
New York is a big town that attracts big personalities. And sometimes the rich and famous go a little overboard and dive into the deep end of erratic and unsightly behavior. The folks at TMZ are experts in reporting every little nugget of celebrity misdeeds on their popular TV show and website, and this bus tour gives you an up-close look at some of the most famous scenes in New York where beautiful people behaved badly. The entertaining guides have the attitude to back up the material, so you can bet you won’t find a better source to describe a Lindsay Lohan meltdown or decadent details of a Charlie Sheen hotel binge with a prostitute. Other stops include the dive bar where Lady Gaga launched her career and the spot where Gerard Butler has impressed the ladies on previous trips to New York. The high-tech tour bus comes decked out with cutting-edge multimedia displays and plenty of clips spiked with that famous TMZ sass.  You also won’t have to wait until tomorrow to find out about the latest celebrity scandal — they run tours seven days a week.

DETAILS: Schedules vary; $45 pp (get tickets!); 51st Street and Broadway;


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