Remnants of Gritty Old Times Square

Uncover the seedy side of NYC's popular tourist hotspot!

Remnants of Gritty Old Times Square

Tour Highlights:

  • Get 50% off as an Insider, Explorer, or Superfan!
  • Learn about the largest sex emporium in New York City (and maybe the world), the freak show where Diane Arbus found her inspiration, as well as the last remaining hot sheet hotel and live peep show in Times Square
  • Discover the dirtiest hotel in America, the oldest building on 42nd Street (it’s not what you think), and the most dangerous block in New York City
  • Visit sites for classic films like Midnight Cowboy (1969) and Taxi Driver (1976)

About this Tour:

Let us take you back to the halcyon days when 42nd Street was the Deuce, Eighth Avenue was the Minnesota Strip, the Great White Way was a red light district, and the Crossroads of the World was XXX-rated. We will see former peepshows, grindhouses, adult book stores, dive bars, hotsheet hotels, sex clubs, porno theaters, and massage parlors–not to mention all three locations of the New York Times. We will discover the personalities who made Times Square what it was: the King of the Peeps; the reclusive genius behind the McDonalds of Sex; the woman who built a gay and S&M porn empire; the slumlord with two suitcases filled with gold and five wives; and the Catholic priest who flew too close to the neon sun and crashed and burned.

The tour will show some graphic vintage photographs which may not be appropriate for all ages.

About Your Guide:

This tour is led by Robert Brenner, a native New Yorker and licensed New York City tour guide. Brenner squandered his misspent youth in the fleshpots of Times Square. He witnessed firsthand the demimonde in all their sordid glory. Unlike many of his contemporaries, he lived to tell the tale—and is unashamed. Brenner is also a member of the Guides Association of New York City, and a docent for the Municipal Art Society of New York City. He has led walking tours of Times Square for the Times Square Alliance, the New York Public Library, and Jane’s Walk.

How do I get this tour for a discount? 

If you are not a member yet, become one today at the Insider tier or higher get a 50% discount on Untapped New York Original walking tours like this!

If you are an Untapped New York Insider, Explorer, or Superfan, simply log in to your account using "Log In" button at the top right of the screen. Once logged in, click on the pink “Book Here” button to book this event!

What if I want to bring a friend who isn't a member?

The more, the merrier! You can book a full-price ticket for a non-member guest on this tour at checkout.

How many tickets can I reserve? 

If you are an Insider level member ($20/month), you can reserve 1 discounted ticket to this event. Explorer-level members ($30/month) or Superfans ($100/month) can reserve 2 discounted tickets. If you are a Support or Enthusiast level member, it’s easy to upgrade your account here for a 50% discount, or purchase a full-price ticket here.

You can reserve as many full-price tickets as are available.

Can’t login to your Insiders account?

Please make sure you are trying to sign in with the correct email address. If you have more than one email address please try logging in with all of them, that will solve this issue 99% of the time. Check out our FAQ for videos and more help documents.

The event is sold out?

In-person tours may have limited capacity and are booked on a first come, first served basis.

But don’t worry! Sometimes spots open up closer to the event date if there are cancellations. We also repeat our most popular events when possible so you will have another opportunity to join us. There are also multiple other members-only events weekly that you can join in!

What if I need to cancel?

If you cancel more than 24 hours ahead of the scheduled event, you will receive a 100% refund. Please be courteous to your fellow Insiders and let us know if you can no longer attend so we can offer your spot to another person.

To cancel your booking, simply click on « cancel booking » in the confirmation email you received upon booking. The confirmation email was sent from messages@fareharbor.com

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