• 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), Taxi Driver (1976) and HBO newly released TV show: The Deuce


Private Tour Price: $350 for up to 10 guests, $35 for each additional guest
What to bring: Comfortable walking shoes.
What to know: The tour is 2-hours outdoors tour; please consult with the MTA for weekend subway schedules and routing changes. This tour will show some graphic content and include descriptions which may not be appropriate for all ages


“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.


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

13-gritty-old-times-square_walking-tour_manhattan_nyc_untapped-cities_12One of  the last standing adult shop in Times Square

11-gritty-old-times-square_walking-tour_manhattan_nyc_untapped-cities_10Father Duffy’s Church: The Holy Cross Church

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

09-gritty-old-times-square_walking-tour_manhattan_nyc_untapped-cities_8The Times Square Theater, abandoned since the early 1990’s

05-gritty-old-times-square_walking-tour_manhattan_nyc_untapped-cities_4Times Square’s iconic NYPD outpost, which used to be an Army recruiting center

01-gritty-old-times-square_walking-tour_manhattan_nyc_untapped-citiesFather Duffy’s statue in Times Square

02-gritty-old-times-square_walking-tour_manhattan_nyc_untapped-cities_1Times Square’s hidden in plain sight sound installation

04-gritty-old-times-square_walking-tour_manhattan_nyc_untapped-cities_3Remnants of the New York Times’ first of three headquarters in Times Square


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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