This unique tour explores the ‘Sinister Secrets’ of the South Street Seaport in Lower Manhattan

Tour of South Street Seaport
Tour guide Zak Risinger shares true crime stories of the South Street Seaport Historic District and Lower Manhattan with tour guests.
Photo by Gabriele Holtermann

Guests at the South Street Seaport who expect a stuffy museum tour filled with boring facts are in for a surprise when they sign up for the Seaport Museum’s “Sinister Secrets of the Seaport” tour of the historic district in Lower Manhattan.

The 90-minute-long, interactive tour, led by tour guide Zak Risinger, director of engagement and public programs for the South Street Seaport Museum,  takes crime enthusiasts to twelve historical crime scenes lurking in the cobblestone streets, historic buildings, and waterfront.

Risinger is entertaining and engaging when he talks about the area’s dark past. The sinister, dubious, and sometimes scandalous stories are ripped from the headlines of newspapers and publications from the 1790s to the 1990s and tell a tale about murder, arson, prostitution, blackmail, and illegal animal fights. The stories involve prominent business people, scorned husbands, New York politicians, crooks, and organized crime. Risinger even has “a bridge to sell.” 

Risinger, who came up with the concept for the tour,  explained they focused on stories with an “unbelievable” factor. 

“It would have been really easy to find stories where people committed crimes out of desperation. There are tons of those,” Risinger said. “So it’s finding people who acted out of opportunity like they didn’t have [commit a crime].” 

Tour guide Zak Risinger shares true crime stories of the South Street Seaport Historic District and Lower Manhattan with tour guests.Photo by Gabriele Holtermann

The tour was made possible with a grant from the Alliance for Downtown New York’s Walking Tour Incubator program, which presents five new walking tours of Lower Manhattan. 

Jonathan Boulware, president and CEO of the South Street Seaport Museum, explained the museum has been conducting tours for years, and the current tour was an iteration of a previous tour that involved “tawdry and sinister things of the Seaport.”

“The seaport Historic District is surrounded by areas that have not been preserved, and there is an area that has been preserved,” Boulware said. “The buildings and the architecture, the storefronts themselves, are all telling the story of New York. So it allows us to use the district as a classroom, as a playground, as a place to invite people into a new understanding of New York.”

The journey through the district’s sordid history started at the Irish bar and restaurant Ryan McGuire on 28 Cliff St., where the tour group of about 15 people mingled before hitting the cobblestones. 

Out-of-towners Melissa Tartari and Mark DeLancey found out about the excursion online.

“I like tours, and it was well-reviewed,” Tartari said. “And this is a part of New York that I’m not as familiar with as with other parts.” 

Tour participants test their inner “Sherlock Holmes” with a trivia game.Photo by Gabriele Holtermann

A trivia game, “Ear for Crime,” based on a 1908 publication, “Criminal Slang,” tested the participants’ inner “Sherlock Holmes.”

The trek took the crime buffs to the former Fulton Fish Market, the Fulton Stall Market, which housed a saloon, Bridge Cafe on Water Street, one of the oldest buildings in New York City, dating back to 1794,  and the Brooklyn Bridge, among other sites.

Jessica and Matthew Moore are members of the South Street Seaport Museum and saw the tour in an email from the Downtown Alliance.

Matthew Moore said they had done other tours, but this one was “unique.”

One of the oldest buildings in New York City on Water Street, dates back to 1794 and has seen its share of crime.Photo by Gabriele Holtermann
The tour stops by the Wavertree, one of the many historic ships at the South Street SeaportPhoto by Gabriele Holtermann

“I thought [the tour] was amazing,” Jessica Moore said. “Zak was very engaging and fun, and I really enjoyed the stories.” 

Both said the historical facts about the buildings were fascinating. Jessica Moore liked the story about the fire at the Fulton Fish Market in 1995, which destroyed one of the two main commercial buildings since it was the “most recent.”

“I’m gonna go home and research that a little bit,” Jessica Moore said. “That was interesting.”

For tickets, go to southstreetseaportmuseum.org/sinister-secrets. Registration is required, and the tours are suitable for ages 13 and up.

Risinger shared that a special “Sinister Secrets of the Seaport” one day before Halloween is in the works.