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The Seaport with steam rising.
Photograph: By Rossilynne Skena Culgan / Time Out

Discover sinister secrets of the Seaport on this true crime-inspired walking tour

This area earned its nickname of "the wickedest ward."

Rossilynne Skena Culgan
Written by
Rossilynne Skena Culgan

Beneath the cobblestone streets of the Seaport, secrets hid underground for decades—until now, that is. A new walking tour led by the South Street Seaport Museum unearths the neighborhood's freaky and fascinating facts.

The museum's "Sinister Secrets of the Seaport" whisks visitors back in time for a 90-minute walking tour full of true crime tales about theft, organized crime, murder and even pirates. Tours are available on November 5, 11, 12, and 29 and December 9, 10, 16, and 17 for $40/adult. Whether you're a true crime buff or you're just soaking up the Halloween spirit, these tours make for a memorable afternoon in a historic neighborhood. 

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“The South Street Seaport District has a sort of sordid past,” Zak Risinger says while leading a recent tour. As director of engagement and public programming at the museum, Risinger developed the tour, which launched this summer. 

All the stories guides tell on the tours were "ripped from the headlines," Risinger explained. Whether or not those stories are actually true, however, is up to each listener, he added.

South Street Seaport Museum at Seaport District in New York City, as seen on Oct 24, 2020.
Photograph: By Ritu Manoj Jethani / Shutterstock

The decades from the 1840s to the 1870s were the height of crime in the area, including an arson at a cutlery company on Cliff Street and a murder involving John C. Colt (of the family associated with Colt guns) at the intersection of Maiden and Water Streets. The details of both incidents are extremely juicy, but we won't spoil it—go on the tour to find out the rest. 

Given the area's location along the water, people arrived here on boats with money to burn—on alcohol, sex and rat fights (seriously). The Seaport earned the nickname "the wickedest ward" for its reputation. 

In addition to learning all the sordid details of those crimes, the tour also includes “Ear for Crime” pop quizzes were you can put your knowledge of true crime to the test. Winning respondents will earn stickers and possibly even a prize at the end of the tour. 

The historic schooner at South Street Seaport, New York
Photograph: By Andrey Bayda / Shutterstock

The South Street Seaport Museum staff developed the tour with support from the Alliance for Downtown New York’s Walking Tour Incubator program. Other tours that received funding through the program include Downtown LGBTQ+ Activism Walking Tour by Christopher Street Tours; How To Be A New Yorker - Downtown Edition; and more.

As for Sinister Secrets, it takes on the scandalous, dubious and sinister tales lurking throughout this historic district. While many stories come from the area's crime heyday in the 1800s, some stories stretch back to the 1790s and others up to the 1990s. It's grim subject matter, of course, but it's delivered in a lighthearted way. You'll never see the Seaport in the same way again.

Each tour begins at Ryan Maguire’s Bar & Restaurant, at 28 Cliff Street, where you'll get one happy hour drink or soda included with registration. Show up early to hear a few scandalous stories inspired by the historical images on view at the bar.

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