How long is the Gritty Old Times Square Tour?

The tour lasts approximately 2 hours.

Where does the tour begin and end?

It starts at the Father Duffy Statue on 7th Ave between 46th and 47th St and ends near 50th St. and 8th Ave.

Is the tour physically demanding?

No, the tour is considered easy but does involve walking on uneven sidewalks and some crowded areas.

Is the tour accessible for people with mobility issues?

The tour covers uneven ground and busy streets; contact the company at tours@untappedcities.com to discuss accommodations.

Is tipping the guide required?

Tips are not mandatory but are always appreciated.

Is this an indoor or outdoor experience?

The tour is mostly outdoors, following streets and sidewalks around Times Square.

Gritty Old Times Square Tour with Untapped New York

Located at 7th Ave & W 47th St in the heart of New York City’s Times Square, Untapped New York’s Gritty Old Times Square Tour offers a raw and unflinching walk back through the neighborhood’s tumultuous past. This two-hour guided journey unpacks the darker side of 42nd Street, once infamous for its adult entertainment scene, dive bars, and neon-lit vice come nightfall.

Times Square today dazzles as a global crossroads for tourists and theater lovers, but decades ago, it held a grittier reputation. This tour walks the same pavement where the largest sex emporium in New York City once operated and pauses at the last remaining live peep show still tucked away in the district. Guides reveal stories about characters who shaped this outlawed nightlife world — from the 'King of the Peeps' to sly slumlords and eccentric pioneers of the red-light underbelly.

More than just a history lesson, the tour points out film locations from classics like Midnight Cowboy and Taxi Driver, situating visitors within a cinematic and cultural framework. The architecture alone tells tales — from the oldest 42nd Street building to hotsheet hotels that once hosted scores of shadowy transactions.

Navigating uneven sidewalks and busy crowds, the experience immerses participants in the sensory overload of past and present Times Square, peeling back layers beyond the typical tourist façade. Untapped New York’s tour serves as a unique window into the lesser-seen, rebellious spirit that has long fueled this corner of Manhattan.

For visitors intrigued by urban history, film, and the complex social fabric of New York City, this tour provides a practical and provocative encounter. It stands apart not just as a walk through tourist-packed streets but as an encounter with the city’s bold, unvarnished stories.

About Untapped New York

Untapped New York is a specialist tour operator based in Jersey City, New Jersey, offering immersive, history-focused experiences across the New York metropolitan area. The company curates guided walking tours, hard hat access trips, private tours, and urban exploration itineraries that reveal hidden architecture, abandoned spaces, and lesser-known cultural stories. Signature experiences include private tours of remnants of Old Penn Station with photographic documentation from noted photographers and railroad historians; Secrets of Grand Central led by award-winning guides; and multiple Ellis Island Hospital hard hat tours that explore century-old contagious disease wards, autopsy rooms, and JR’s "Unframed" exhibition. Other offerings include underground subway explorations, Gilded Age mansions walks along Fifth Avenue, and thematic cultural routes such as NYC’s Irish History Tour.

Tours are presented as focused, small-group experiences—private and public—designed for visitors and locals who want deep historical context and rare access. Untapped New York highlights tangible artifacts and architectural remnants, combining storytelling with visual materials to enrich each tour. The company works with specialist guides, photographers, and historians to document locations factually and compellingly. Booking options include private tours and scheduled public departures for select trips. Whether exploring abandoned hospital wards, hidden stations, or the opulent façades of Millionaire’s Row, Untapped New York emphasizes archival research, expert-led narration, and unique on-site photographs to convey the layered history of New York’s built environment. Scheduled experiences feature Remnants of Penn Station, Secrets of Grand Central, Ellis Island Hospital Hard Hat Tours, NYC’s Underground Subway Tour, Fifth Avenue Gilded Age mansion walks.