As part of our spring and summer line-up of experiences, including our brand new Secrets of Prospect Park walking tour, Untapped Cities is bringing back our tour of the Remnants of Gritty Old Times Square! New dates have just been added from now until June and tickets are on sale now. Read on to learn more about this tour and to book your spot.

Gritty Old Times Square

This tour will take you back to the Gritty Old Times Square of the 1970’s, a world featured in HBO’s hit series The Deuce. Back then, Times Square was a dangerous, exciting, gritty, intense, racially and sexually diverse neighborhood frequented by both locals and tourists. Love it or hate it, you couldn’t ignore it. Most of old Times Square has been carefully obliterated by generic hotels, soulless office buildings, and Walt Disney musicals, but there are still a few vestiges of its seedy past—if you know where to look.


  • 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)

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.

10-gritty-old-times-square_walking-tour_manhattan_nyc_untapped-cities_9The now abandoned Elk Hotel, a relic of what Times Square used to be

Gritty Old Times Square


Price: $35

What to bring: Comfortable walking shoes

What to know: The tour is two-hours long and will show some graphic content and include descriptions 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.

15-gritty-old-times-square_walking-tour_manhattan_nyc_untapped-cities_14One of  the last standing adult shop in Times Square


“Our guide, Robert Brenner, was in full command of his material including both social and architectural history. He can talk about the roughest and sleaziest times and characters without ever denigrating them or his listeners. Truly informative and interesting tour that brings a bygone era back to life.” — shecasey, Trip Advisor

“Great information about the way Times Square used to be in the 70’s and 80’s. There are a few grimey places still left but you really need a guide to show you where they are and you should go soon as even these will be gone soon.” — Darby666, Trip Advisor

“Great tour of Old Times Square. The “seedy” side of Times Square. Our guide was very informed and it was a blast to hear the history behind some legitimate theaters. The days of peep shows and porn theaters may be gone but always remember your history” — Cassysj, Trip Advisor

“Opening my eyes in Times Square. A very fun an interesting Sunday morning, seeing old buildings anew and hearing new stories about Times Square even though I’ve lived here 35 years.” — PeterFNyc, Trip Advisor.


Father Duffy’s Church: The Holy Cross Church

The Times Square Theater, abandoned since the early 1990’s

Times Square’s iconic NYPD outpost, which used to be an Army recruiting center

Father Duffy’s statue in Times Square

Times Square’s hidden in plain sight sound installation

Remnants of the New York Times’ first of three headquarters in Times Square

Gritty Old Times Square

Check out all of our Behind the Scenes Tours.