The City of London, often referred to as the "Square Mile," is no stranger to scandal and intrigue. The Scandalous Square Mile walking tour promises to take visitors on a thrilling journey through the district’s notorious past. Guided by a qualified expert, the tour uncovers the dark underbelly of this financial hub, delving into the secrets of its famous landmarks, the site of London’s infamous prison, and the real-life inspiration behind a scandalous Game of Thrones scene. But the tour’s most captivating revelation may just be found at the end, where visitors can raise a glass to the city’s dodgiest doctor at a pub named after the notorious Jack Sheppard.
Key Points

- This walking tour explores the dark and scandalous past of London’s financial district, the Square Mile, showcasing its notorious history.
- The tour uncovers the secrets of famous sights, including the location of London’s most notorious prison and the site of the ‘walk of shame’.
- Participants learn about the grim history and harsh conditions of the infamous prison, as well as the stories of its most notorious inmates.
- The tour visits the location that inspired a Game of Thrones scene, recounting the historical events and shaming rituals that took place there.
- The journey culminates at a pub named after the notorious Jack Sheppard, where visitors can raise a glass to his colorful life and death.
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Contents
- Key Points
- Overview of the Walking Tour
- Exploring the Dark Side of the Square Mile
- The Site of London’s Notorious Prison
- The Real-Life Walk of Shame
- Raising a Glass to London’s Dodgiest Doctor
- Scandalous Past of Moorgate
- Uncovering the Secrets of Famous Sights
- Smithfield: Carnivals and Grisly Executions
- Frequently Asked Questions
- Is the Tour Suitable for Children?
- Can We Take Photos During the Tour?
- Is the Tour Wheelchair Accessible?
- Are There Any Toilet Breaks During the Tour?
- Can We Purchase Tour Merchandise Onsite?
- Recap
- Our Top Picks in London
- More Walking Tours in London
- More Tours in London
- More Tour Reviews in London
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Overview of the Walking Tour

This 1.5-hour City of London Walking Tour explores the dark and scandalous past of the Square Mile, offering participants a glimpse into the city’s notorious history.
Led by a qualified Green Badge guide, the tour showcases the seedy underbelly of the financial district, from the site of London’s most infamous prison to the pub that bears the name of the city’s dodgiest doctor.
Along the way, visitors will walk the real-life ‘walk of shame‘ that inspired a scene in Game of Thrones and uncover the secrets behind famous landmarks like Guildhall Yard and St. Paul’s Cathedral.
The tour wraps up in the Smithfield area, which was once the scene of raucous carnivals and grisly executions.
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Exploring the Dark Side of the Square Mile

The tour’s exploration of the dark side of the Square Mile begins at Moorgate, a modern-day financial center with a scandalous past. The guide leads visitors through the area, uncovering the secrets of famous sights like Guildhall Yard, the church of St Mary le Bow, and the churchyard of St Paul’s Cathedral.
Along the way, they’ll learn about London’s notorious prison that once stood in the area and the ‘walk of shame‘ that inspired a scene in Game of Thrones.
The tour culminates in the Smithfield area, which was the site of some of the city’s most raucous carnivals and grisly executions.
Throughout the journey, the guide paints a vivid picture of the Square Mile’s dark history.
The Site of London’s Notorious Prison

One of the key sites explored on the walking tour is the location of London’s most notorious prison, which once stood in the Square Mile.
Participants will step back in time to the site where this infamous prison once loomed, learning about its grim history and the fate of those who were imprisoned there.
The guide will recount the stories of the prison’s most infamous inmates and the harsh conditions they endured, painting a vivid picture of this dark chapter in the city’s past.
The Real-Life Walk of Shame

As the tour moves from the site of London’s notorious prison, guests are taken to a location that inspired a scene in the hit show Game of Thrones – the real-life ‘walk of shame’ in the City of London.
The guide leads the group through the narrow streets, recounting the historical events that took place here. Visitors learn about the shaming rituals that were once common, where women accused of moral transgressions were forced to walk through the streets, exposed and humiliated.
The tour highlights the power dynamics and social stigma of the time, drawing parallels to modern-day issues of gender and justice. As the group stands in the very spot where these events unfolded, the weight of history hangs palpably in the air.
More Great Tours NearbyRaising a Glass to London’s Dodgiest Doctor
Guests on the walking tour end their journey at a pub that bears the name of London’s most infamous doctor, where they raise a glass to his notorious legacy.
The pub in question is the notorious Jack Sheppard, named after the 18th-century thief, prison-breaker, and criminal celebrity.
As they sip their drinks, visitors learn about Sheppard’s colorful life and death, including his daring escapes from Newgate Prison and his eventual hanging at Tyburn.
The pub’s atmosphere, with its dark wood paneling and dimly lit corners, perfectly captures the seedy underbelly of Georgian London that Sheppard inhabited.
Raising a glass here is a fitting end to a tour that explores the city’s most scandalous and salacious secrets.
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Scandalous Past of Moorgate
The walking tour starts at Moorgate, a modern-day financial hub that conceals a scandalous past.
Once a hub for criminal activity, the area surrounding Moorgate station has a sordid history that visitors uncover during the tour. Guests learn about the area’s notorious reputation, from its origins as a site for public executions to its later role as a haven for illicit activities.
The guide delves into tales of corruption, smuggling, and underground gambling dens that thrived in the shadows of Moorgate’s respectable façade. As the tour progresses, participants gain a deeper understanding of how this seemingly mundane location was once a breeding ground for London’s most notorious characters and scandals.
Uncovering the Secrets of Famous Sights
After exploring Moorgate’s scandalous past, the tour moves on to uncover the secrets behind some of the City of London’s most famous sights.
Participants explore the intriguing histories of landmarks like Guildhall Yard, the church of St Mary le Bow, and the churchyard of St Paul’s Cathedral, discovering the hidden stories that lie beneath their seemingly ordinary facades.
At Guildhall Yard, they’ll learn about the site’s role as a meeting place for London’s elite, while the church of St Mary le Bow boasts a fascinating connection to the legend of Bow Bells.
The tour then ventures into the churchyard of St Paul’s Cathedral, uncovering tales of the site’s grisly past.
Smithfield: Carnivals and Grisly Executions
The tour concludes in the Smithfield area, which was the site of some of London’s most raucous carnivals and grisly executions throughout history.
Smithfield served as a public execution site for centuries, with notorious criminals and religious dissenters meeting their end on the gallows.
However, the area also played host to lively fairs and festivals, where Londoners would gather to eat, drink, and be entertained.
Visitors can see the Smithfield Market, one of the oldest meat markets in the country, and imagine the rowdy atmosphere that once filled the streets.
The contrasting history of Smithfield – from carnivalesque revelry to brutal punishment – provides a fitting end to this tour of London’s scandalous past.
Frequently Asked Questions
Is the Tour Suitable for Children?
The tour may not be suitable for children as it covers the city’s dark and scandalous history, including prisons, executions, and other adult themes. It’s recommended for an adult audience interested in the city’s more salacious past.
Can We Take Photos During the Tour?
Yes, guests are generally permitted to take photos during the tour, unless otherwise instructed by the guide. However, visitors should be mindful of respecting others’ privacy and any restrictions that may apply at certain sites along the route.
Is the Tour Wheelchair Accessible?
The tour is not explicitly advertised as wheelchair accessible. Visitors with mobility challenges should contact the tour provider in advance to inquire about accessibility accommodations and ensure the tour route can be navigated safely.
Are There Any Toilet Breaks During the Tour?
The tour does not explicitly mention any scheduled toilet breaks. However, as a walking tour, there may be opportunities for participants to use restroom facilities during the stops along the route, though this is not guaranteed. It’s best to plan accordingly.
Can We Purchase Tour Merchandise Onsite?
Unfortunately, no tour merchandise is available for purchase on-site. The focus of the tour is on providing a unique historical walking experience rather than selling additional products. Visitors should come prepared with comfortable shoes and a curiosity for London’s scandalous past.
The Scandalous Square Mile: City of London Walking Tour
Recap
The Scandalous Square Mile tour takes visitors on a captivating journey through the City of London’s sordid past.
From notorious landmarks to scandalous tales, the tour unveils the dark and seedy underbelly of the financial district.
Culminating at a pub associated with one of London’s most infamous outlaws, this thrilling walking experience offers a unique glimpse into the capital’s scandalous history.
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