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Tour the Remnants of Gritty OId Times Square

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2 travellers
What to Expect
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.

• Learn about 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)


Price: $35 (+fees)

What to bring: Comfortable walking shoes

What to know: The tour is two-hours long and will show some graphic vintage photographs which may not be appropriate for all ages. Please consult with the MTA for weekend subway schedules and routing changes.

ABOUT YOUR TOUR 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.
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Important Information
Departure Point
We will meet in front of the statue of Father Duffy on the north end of Duffy Square. 7th Ave & W 47th St, New York, NY 10036. Please do not confuse it with the statue of George M. Cohen on the south end of Duffy Square.
Departure Time
  • Food and drinks
  • Gratuities
  • Hotel pickup and drop-off
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Additional Info
  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Tour is in English
  • Comfortable walking shoes are recommended
  • The tour is 2-hours long
  • This tour/activity will have a maximum of 20 travelers
Cancellation Policy
All sales are final and incur 100% cancellation penalties.
Reviews (4)
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Reviewed May 28, 2019 via mobile

Guide Brenner has a clear passion for his well-researched subject matter. He takes the group to places previously known for being filthy (either unclean, sordid or both). He offers his take as a born and raised New Yorker supplemented by photographs of what once was....More

Date of experience: May 2019
1  Thank Fattermatter
Augustin-Pasquet, Owner at Untapped Cities, responded to this reviewResponded June 3, 2019

Thank you very much for coming on this tour and leaving a great review! Glad you enjoyed this unique tour!

Reviewed April 30, 2019

'' Take this tour before the old Times Square completely disappears. Robert is very well informed and has a wealth of information about the old and new Times Square. MUST SEE ! ''

Date of experience: April 2019
1  Thank Gildo S
Augustin P, Owner at Untapped Cities, responded to this reviewResponded May 1, 2019

Thank you very much!

Reviewed April 29, 2019

This is such a great tour. See the remnants of the good ol' days when Times Square had peep shows, pimps, and prostitutes and you could pay for a hotel by the hour. Robert is a great guide, bringing a wealth of knowledge and first-hand...More

Date of experience: April 2019
2  Thank heathers607
Augustin P, Owner at Untapped Cities, responded to this reviewResponded April 29, 2019

Thank you Heather! Really glad you enjoyed this unique experience

Reviewed September 25, 2018

The Remnants of Gritty Old Times Square tour (by Robert Brenner) was a completely surreal experience. Modern day Times Square is arguably a soulless area with generic megastores and restaurant chains built for tourists and avoided by locals. Not long ago in the ‘70s and...More

Date of experience: September 2018
2  Thank Edward T
Augustin P, Owner at Untapped Cities, responded to this reviewResponded October 1, 2018

Thank you very much Edward!

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Questions & Answers
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June 3, 2019|
Response from Fattermatter | Reviewed this property |
Yes. He goes about once a month but you can contact directly if you have a group that wants to schedule a private tour as he is an independent tour guide.
Key Details
  • Untapped Cities
  • Duration: 2h
  • Mobile Ticket Accepted
  • Instant confirmation
  • Languages Offered: English
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