Sinister Secrets of the Seaport Walking Tour

Saturday, Oct 11, 2025 from 2:30pm to 4:00pm

  212-748-8600
  Website

Join this 90-minute walking tour that takes you on a winding journey to unravel the darker past of the South Street Seaport Historic District and Lower Manhattan. 

This entertaining tour tells the scandalous, dubious, and sinister tales lurking in the cobblestone streets, historic buildings, and waterfront. Throughout the tour, your guide shares historical stories ripped from the headlines of newspapers and publications from the 1790s to the 1990s that provide a new perspective on the history of the area that helped to make New York a global metropolis. You can also test your “Ear for Crime” in an interactive game throughout the walk, which even has a prize for the winner at the end of the tour.

Meet your tour guide at Ryan Maguire’s Bar & Restaurant, at 28 Cliff Street, where one happy hour drink or soft drink is included in your registration for the tour. Come up to 30 minutes early and be treated to a few scandalous stories inspired by the historical images on view at the bar. 

Registration is required. Tours are rain or shine. Content is appropriate for fans of true crime stories, those who are looking for unique New York experience, and history-buffs aged 13 and up.

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