The Outlaws Who Built NYC Walking Tour

Uncover the Hidden Backstory of New York City’s Outlaws for Just $32

The Outlaws Who Built NYC Walking Tour offers a fascinating look into the criminal and shady figures behind the city’s growth. Priced at $32 per person and lasting approximately 2 hours, this tour is ideal for those interested in NYC’s darker history. It departs from Lower Manhattan and covers key sites linked to gangsters, pirates, and corruption. The tour is led by an expert guide, praised for their enthusiasm and knowledge, making the experience both entertaining and informative. With a small group limit of 15, participants enjoy a personalized exploration of New York’s shadowy past.

This tour suits travelers eager to see lesser-known parts of Manhattan and learn about famous criminals, con artists, and law enforcement origins. While the pace is fast and the focus on gritty history might surprise those expecting a typical sightseeing tour, it offers unique insights you won’t find in standard guides.

Key Points

• Affordable price at $32 for a 2-hour walk through Manhattan’s criminal history.
• Expert guide with enthusiastic storytelling praised by previous participants.
• Stops at significant sites like Wall Street, Trinity Church, and the East River Waterfront.
• Focus on NYC’s shady founders, pirates, and the origins of law enforcement.
• Small group size enhances the personalized experience.
• Free stops with no additional admission fees, exploring iconic and hidden locations.

The Tour Starts at Millennium Downtown New York

The tour begins outside the Millennium Downtown New York hotel at 55 Church St, a central spot near major subway stations and ferry terminals. 3:00 pm is the set start time, making it a convenient late-afternoon outing. The meeting point is easy to find, and the tour concludes at the historic White Horse Tavern at 25 Bridge St in the Financial District.

The location provides quick access to public transportation, ideal for combining with other sightseeing plans. The small group size of up to 15 travelers ensures that the guide can offer plenty of attention and engaging stories.

Exploring the Site of NYC’s First Privateers at Oculus World Trade Center

The first stop takes visitors to the Oculus at the World Trade Center, where the guide shares stories about early privateers in NYC’s history. You’ll see the remains of ships embedded in the earth, revealing the city’s maritime and piracy roots. This spot sets the tone for uncovering seafarers and outlaws who shaped New York’s early days.

This brief stop lasts about 7 minutes, but it’s packed with insights into how smugglers and pirates contributed to the city’s growth and illegal trade. The site’s modern architecture contrasts starkly with its gritty history, offering a visual reminder of NYC’s layered past.

The Site of Madame Restell’s Business at the 9/11 Memorial & Museum

Next, the tour visits the National 9/11 Memorial & Museum, focusing on the location that once housed Madame Restell, a notorious 19th-century abortionist and con artist. This site illustrates the secretive, often illegal, activities that thrived in NYC’s past, laying the groundwork for broader social and legal transformations.

With about 7 minutes here, the guide discusses underground remedies and shady dealings that contributed to NYC’s future. The memorial’s somber atmosphere adds weight to the stories of outlaws who pushed boundaries.

The First Black Millionaire’s Former Home

Another short stop at the 9/11 Memorial & Museum spot highlights the location of NYC’s first Black millionaire’s residence. This reveals a different aspect of the city’s history—wealth built through daring and sometimes illicit means—and provides a broader understanding of NYC’s diverse power players.

The site serves as a reminder that shady dealings and ambition have long been part of the city’s fabric. This stop lasts around 6 minutes, offering a quick but meaningful glimpse into the complex social tapestry of Manhattan.

Trinity Church Wall Street and the Fight for Press Freedom

At Trinity Church Wall Street, the guide shares stories about a trial that established the Freedom of the Press. This historically significant event connects church authority to free speech rights, highlighting the intertwined nature of law, power, and dissent in New York.

A brief 6-minute stop, it offers insight into the legal battles and political intrigue that influenced NYC’s development. The site’s architecture and history make it a fitting place to explore the city’s fight for independence and transparency.

The 1920 Wall Street Bombing

The tour then visits the famous Wall Street location of the 1920 bombing, a shocking act of violence linked to criminal and political tensions of the era. The guide explains how this incident reflected the violent side of the city’s financial hub and its connections to organized crime.

This stop lasts about 7 minutes, focusing on the tumultuous history of Wall Street and how criminal elements affected the city’s financial reputation. It’s a vivid reminder of NYC’s sometimes dangerous past.

Manhattan Company and NYC’s Water and Banking Origins

Another key site is Wall Street’s Manhattan Company, which played a role in water supply and bank formation. The guide describes how criminals and entrepreneurs intertwined in building the city’s infrastructure, blurring lines between legitimate business and illicit activities.

This 7-minute stop sheds light on the city’s early financial institutions and their shady beginnings, emphasizing the role of outlaws in shaping NYC’s economy.

Brooklyn Bridge’s Corrupt Beginnings from the East River Waterfront

The East River Waterfront Esplanade offers a birds-eye view of Brooklyn Bridge, famed for its rough and corrupt origins. The guide discusses bribery and shady dealings involved in its construction, revealing a darker side of iconic infrastructure.

This 7-minute stop combines stunning views with stories of cover-ups, corruption, and ambitious engineering, illustrating that even symbols of progress often have secret histories.

Law Enforcement and Police Corruption in the 1970s

Moving into more recent history, the tour covers the First Precinct in the Financial District, exploring police corruption during the 1970s. The guide details law enforcement’s complex relationship with criminal elements, revealing how officials played both sides during a tumultuous period.

At this 7-minute stop, visitors gain an understanding of the challenges of maintaining law and order in a city riddled with organized crime and political pressure.

Captain Kidd and Colonial Criminal Ties at Hanover Square

At Hanover Square, the story of Captain Kidd, one of the most infamous pirates, unfolds. The guide explains his influence on colonial development and how criminals helped shape early New York. This ties into the broader theme of outlaws as builders of the city.

This short stop lasts 7 minutes, offering a look into the pirate’s role in colonial NYC and how criminal enterprise contributed to the city’s growth.

The Home of New Amsterdam Law-Breakers at the White Horse Tavern

The tour concludes at the White Horse Tavern on Bridge Street, on the site once inhabited by law-breakers from New Amsterdam. These early outlaws helped create the social elite, and the site ties together the tour’s themes of crime, influence, and city-building.

Spending 8 minutes here, visitors reflect on the seedy origins of NYC’s upper class and the long-standing link between shady dealings and social mobility.

Practical Details and Tour Experience

This 2-hour walking tour is designed for those with an interest in NYC’s criminal past and hidden histories. The small group size ensures a more engaging experience, and the free stops provide a chance to explore famous and obscure sites alike. The guided commentary is well-received, with reviewers praising the knowledgeable and enthusiastic guides.

While the pace is brisk, the tour offers a well-structured narrative that balances famous events with lesser-known stories, making it ideal for history buffs and curious explorers. The tour’s focus on shady figures and corruption makes it a distinctive alternative to traditional Manhattan sightseeing.

The Sum Up: A Unique Look at NYC’s Shadowy Foundations

The Outlaws Who Built NYC Walking Tour stands out for its focus on the city’s criminal and shady origins, offering a rare glimpse into how outlaws, pirates, and corruption helped shape Manhattan. It’s best suited for history enthusiasts eager to go beyond the usual sights and explore the darker side of New York’s development.

With affordable pricing and enthusiastic guides, this tour delivers entertaining and insightful stories in a compact 2-hour format. It provides an accessible and engaging way to learn about NYC’s hidden past, making it a worthwhile addition to any exploration of the city’s history.

Frequently Asked Questions

What is the cost of the tour?
The tour costs $32 per person.

How long does the tour last?
It lasts approximately 2 hours.

Where does the tour start and end?
It begins at 55 Church St, outside the Millennium Downtown New York hotel, and ends at White Horse Tavern on Bridge St.

Is the tour suitable for all travelers?
Most travelers can participate, and service animals are allowed. The pace is brisk, so comfortable footwear is recommended.

What are some notable stops?
Key sites include Oculus at World Trade Center, Wall Street, Trinity Church, and East River Waterfront with views of Brooklyn Bridge.

Are there any additional costs?
No, the stops are free of charge, and the tour fee covers the entire experience.

What makes this tour different from others?
It focuses specifically on NYC’s criminal history, pirates, and corruption, offering stories not typically covered in standard city tours.

Can I cancel the tour if needed?
Yes, there is free cancellation available up to 24 hours in advance.