Strolling through Times Square today, it’s difficult to envision the neighborhood as a dangerous, gritty, intense, racially and sexually diverse place. 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 from the 1970s—if you know where to look.

On our April 30th tour of Gritty Times Square, we’re taking 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.

Gritty Old Times Square

Led by native New Yorker, Robert Brenner, the tour will include highlights like the largest sex emporium in New York City, 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 and the most dangerous block in New York City. We’ll also visit sites for classic films like Midnight Cowboy (1969) and Taxi Driver (1976).

One of  the last standing adult shop in Times Square

One of  the last standing adult shop in Times Square

Father Duffy’s Church: The Holy Cross Church

The now abandoned Elk Hotel, a relic of what Times Square used to be

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.