Private Remnants of Gritty Old Times Square Tour

Remnants of Gritty Old Times Square Tour

Tour Highlights

  • 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)

Guests Love This Tour!

  • 5 star ratingGreat 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.”


    5 star ratingOur 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.”

  • 5 star ratingOpening 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.


    5 star ratingGreat 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”

  • 5 star ratingA well researched glimpse into a fast disappearing part of NYC history 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. Definitely not for children, this tour offers a glimpse into the fascinating world of the sordid 70s and 80s New York of prostitutes, drugs and peepshows.

    Jab Avatar

    5 star ratingTake a trip back in time when NYC looked like a B+W Film… 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 !

    Gildo S Avatar
    Gildo S
  • 5 star ratingSeedy, Smutty, Shady – I loved it! 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 experience to this tour having grown up in New York. An enthusiastic two thumbs up!

    Heather S Avatar
    Heather S

    5 star ratingYou’ll never look at Times Square the same way again 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 ‘80s, Times Square had a far grittier and fascinating past. Our historian and tour guide, Robert provided detailed background stories of key characters and displayed photos of several landmark buildings from that era including theaters, hotels, restaurants and offices. He took us to original buildings and facades that have survived demolition and reconstruction. He was able to connect buildings and locations to those portrayed in the highly rated TV show, The Deuce, currently in second season. We were stunned to learn that Times Square locations we ate at and visited were originally infamous locations from The Deuce or significant theaters from that era. There are hotels in Times Square that have such epic gritty stories you have to hear about – such legendary experiences do not occur anywhere else in the world. I guarantee you won’t ever look at Times Square the same way again and that you’d agree the bygone Times Square of the ‘70s and ‘80s was a far more interesting and captivating place than the sterile version we see today.

    Edward T Avatar
    Edward T

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.


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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