4 Walking Tours for Experiencing London’s Darker Side

Front gate archway of St Olave Hart Street in London, UK

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Walking tours weren’t on my radar until recently. I was aware of them before now but not with any knowledge of how they operated. Previously, my idea of a tour usually involved a swarm of people in shorts, sunglasses and holiday hats. They’d be constantly snapping photos, and they normally packed onto a bus.

So I was pleasantly surprised when I discovered they could be engaging, personal and interactive as well as informative. And, above all, they can be a lot of fun!

Walking tours are a great way to immerse yourself into a city’s culture. Luckily, London has LOADS to choose from, and we went on quite a few while we were there. Our London street art tours were apparently just the tip of the iceberg!

Here are a few more of our favourites that you can and should do, particularly if you are a dark tourist, or generally interested in dark tourism, as these tours lean more towards the macabre.

Reader discretion is advised!

A note of caution: Please check the age preference for these tours. There are plenty of awesome and free things to do in London with kids, some of these might not be it…

​Jack the Ripper Walking Tour

– Thursdays & Saturdays at 6PM (rain or shine)
– Approximately 2 hours
– Pay what you think it’s worth
NOT suitable for children under 12
– Book online HERE

The first of our London walking tours was one of the most popular, especially in October. From those available, it certainly leapt out at me, which may be why we did it first. I had seen TV shows and films about Jack the Ripper, but always as fictional stories rather than documentaries. I looked forward to learning the facts from the fiction.

Tower of St Botolph's Aldgate church, the Prostitute's Church in Whitechapel, London UK
Our meeting place for the start of the tour

We met our tour guide, Sinead, in the middle of the Whitechapel district where the murders took place. Our group was entirely adults, apart from a boy who appeared to have come along with his mother. He looked to be no older than ten (despite a 12+ advisory). I wondered how he would take it, knowing some of what was to come. Our guide even started with a warning about the graphic nature of the tour.

And graphic it was – Sinead spared no detail in her descriptions of the crime scenes we visited. To do so would do a disservice to the victims, she said. Jack the Ripper was originally suspected to have been a butcher by trade, which gives you some idea of what he did to the people he killed.

We visited three of the five murder sites (two no longer exist). We also saw the building that it is believed Jack hid from the police on the night of the double murder, and the pub and church the victims all frequented. Sinead’s insights into the ferocity and the extent of the attacks made the evening seem quite surreal to me.

What grounded the whole thing for me is the fact that much of the landscape is still the same as then. For example, you can still have a pint at The Ten Bells Pub, the pub favoured by each of the victims. The building Jack the Ripper hid in is still standing, although the entrance he used is now a Fish & Chip shop. 

While we were on the tour, we passed by the entrance to the hostel we were staying in. Apparently, we had inadvertently booked a place right in the heart of Ripper territory (we recommend the place, though!). Even though it had all happened back in 1888, knowing that still did not do wonders for my sleep. It’s sobering to know that people like that can exist.

Street art by Otto Schade depicting a silhouette of Jack the Ripper in Shoreditch, London UK
​Even the street art embraces local dark history – main art by Otto Schade

For those not of a nervous disposition or averse to injury detail, you can arrange to go on the Jack the Ripper tour here.

RELATED: The Best Dark TV Series for Dark Tourists

Side note from Dagney

I initially did a Jack the Ripper walking tour nearly 20 years ago when I was 12 (and think the advisory of 12+ is well advised, but on a case by case basis as not every kid is the same; I would have been fine at any age).

I’ve always been one of those weirdos fascinated by the darker side of life. When Sinead mentioned THE definitive Jack the Ripper website, I laughed and said to Jeremy, “That’s the first site I ever bookmarked!” Although I don’t remember it all (memory of a goldfish), it was interesting to see how the case had evolved over time. Despite it being over 100 years ago, the discoveries made in the last 20 years are phenomenal. Though sadly, we will never know who Jack the Ripper was. 

Anyway, what actually stood out to me the most, was that when I did the tour 18 years ago, it was very different. For one, I remember it being more about the storytelling than the facts. In part because there were a lot less of them then. But some tours I think do still go for theatrics over historical record, so that is something to keep in mind.

However, what struck me was that this tour – and most of the Jack the Ripper walking tours running today – now go through the Whitechapel area. This wasn’t true probably even 5-10 years ago, and certainly not 18 years ago. We went through the the London Tower area originally (some still do, I believe). This is because, like it was back in 1888, Whitechapel has historically been one of the poorest neighbourhoods in London. Due to mass gentrification, this has now changed, altering much of the area (as Sinead said on our tour “First the Jews came, then the Bangladeshis and now the Hipsters, gentrifying everything in their wake.”) This means these London walking tours are simultaneously more authentic feeling, and less so at the same time.

A creepy street art we found during one of our London walking tours

​Dark Side of London Walking Tour

MOST Tuesdays at 7PM & Thursdays at 6PM
– Approximately 2 hours
– Pay what you think it’s worth
– Book online here

This turned out to be one of the more information-based excursions and I’m glad this is the case. The tour runs all year round but with Halloween approaching I didn’t know how much that would affect the content. We’re not big fans of “supernatural” shenanigans. Historical stories of creepy true events? We’re in. Spooky stories about people claiming to have seen or heard ghosts? That’s OK too. But using divining rods to try and actually contact the dead? Hard nope.

So when our guide, Matt, started with a tale about the ghost of a murdered child, I braced myself. Which way was this going to go? Is he going to start chanting or become “possessed”? Fortunately that story turned out to be the most supernatural element of our experience, and the rest was all darkly, horribly true. Excellent!

From there we covered the whole breadth of London’s darkest times. We heard how Bloody Queen Mary publicly boiled non-Catholics alive in oil in the 1500s (because burning people to death was too quick to make an impression). Matt took us to the church of St Bartholomew the Great, who according to legend was flayed alive. As such he’s often depicted in art holding his own skin like a jacket. What a lovely image.

Matt also had quite a few little pieces of trivia up his sleeves. Did you know London has enough public park space to bury 4 million people, should there be another plague, or other uncontrollable epidemic? That’s half of London’s population! Or that an outbreak of cholera in 1854 can be traced to a single water pump on Broadwick Street? Apparently, the drunks survived better than sober folk in that time, as they drank beer instead of water (which was infected). This led a man named John Snow (no, not that one) to determine that cholera is waterborne, not airborne (as widely believed at the time). Although not recognised during his lifetime, this discovery eventually helped to influence improvement in sanitation in London. It also led to a pub on Broadwick street being named after him!

WWII Walking Tour ourside ruins of St Dunstan-in-the-East church in London, UK
​How many cholera victims might be buried here?

Despite many eye-opening stories and pleasing facts our tour finished on a particularly morbid note. Our last stop was on a street through which one of the most prolific serial killers was lead on her way to being hanged.

Amelia Dyer was a former nurse who took in unwanted infants in the 1800s. For a fee you could leave your child with her to be raised in her care. Unfortunately after she acquired the child and the fee she would kill it and dispose of it in the river. Before she was caught and executed, it’s estimated she was responsible for the deaths of over 400 infants. The real number is not known.

I still cannot quite get my head around how someone could do that to a child, let alone hundreds. But I must admit, it was morbidly fascinating to hear about on the tour.

To take part for yourself, you can reserve places in a group here.

​World War Two Walking Tour

MOST Fridays & Sundays at ​2PM
– Approximately 2 -2.5 hours
– Pay what you think it’s worth
– Book online here

At two and a half hours this was the longest of the London walking tours we signed up for. It also covered the most ground, leading us from the Blackfriars area to the Tower of London. There was a reason for this – Canice, our guide for the afternoon, was new to this particular tour. He advised he had only run it a few times before us, and was still working out the kinks. “I have a tendency to go on too long,” he advised with a knowing smile.

There was certainly a lot to go on about! Canice had a wealth of information for each stop, and answered questions from the group as we walked. Now, WW2 isn’t entirely our thing. I never covered the subject in history class at school, and Dagney and I aren’t fussed about military action. Fortunately, Canice’s main vocation is acting, and he painted a vivid and engaging picture of wartime London. I could imagine the roar of the airplanes, and the rumbling of bombs raining down on the city.

WWII Walking Tour outside St Paul's Cathedral in London, UK
​Damage from the Blitz is still visible today

One story that Canice told I found to be particularly extraordinary. During the Blitz of 1940-41, bombing raids were carried out on civilian areas across Britain. The city of Coventry was devastated, and the German air force tried to do the same to London. During a night raid, a bomb fell on the roof of St Paul’s cathedral. But, because of the delay on the fuse, it didn’t immediately explode. As firefighters tried to reach it to remove it, the bomb burned through and fell into the main building.

WWII Walking Tour outside St Paul's Cathedral in London, UK | Cultura Obscura Travel Blog #darktourism #walkingtours #london #plague #plaguewalk #macabre #plaguedoctor
​Would you believe a bomb went off in here?

In another universe that would perhaps have been the end of the cathedral. But the bomb exploded in mid-air before it hit the floor. It was enough force to make the whole roof jump slightly, but St Paul’s survived. In the morning it was still standing, and that fact helped cement the resolve of the British during the war.

To hear more tales of derring-do first hand, just head here.

​T​ales of Plague Walking Tour

– Saturday at 2PM
– 2 hours
– £10 per person (£9 for concessions)
Not suitable for children under 12
– Book via email or phone (details here)

Something more light-hearted to finish with now (though you might not think so from the title). This was the most theatrical of the dark London walking tours we went on, and seemed to be geared towards younger attendees (however, there is a 12+ advisory). But as a moderately immature adult with a childish sense of humour, it worked for me just fine.

Plague walk walking tour demonstration in London, UK
​Live action storytelling!

We had two guides this time: Marianne and Jonathan. Or rather, we had Marianne and a whole host of period characters from the different plague eras! During our tour, Marianne provided us with a whole host of information. On the way, through the means of various costumes and props, we encountered a 14th century peasant, his trusty rat on a stick, a sinister plague doctor and even noted diarist Samuel Pepys.

A visit from the plague doctor during plague walk in London, UK
​The plague doctor was particularly sinister

​At one point, we were even joined by an unintelligible man who appeared to be drunk out of his mind. Though that turned out to not be a part of the tour, and we were swiftly led away after he started rambling and spitting on the ground.

Each one of the (intended) characters gave their colourful impression of the times they lived in. It turns out there are a lot of bodies from times of plague buried all over the city. The Black Death may have killed as many as 100 million people around the world in the 14th century. When there was another outbreak in 1665, almost 70,000 people died in London alone.

A toy rat on a stick, a prop used during one of our London walking tours
​Trusty sidekick and convenient tour group leading device

As more of underground London is explored, mainly due to development, even more mass graves are being discovered. A general rule of thumb seems to be: if you’re in London, chances are someone died where you’re standing.

List of reasons people died during the plague
​A list of fatalities in one week during the plague

​For a more jovial look at one of the worst medical crises in history, reserve your spot​ here.

More London Walking Tours

London is literally teeming with dark history walking tours, and we are only human. There are still so many more we want to experience, and here are just a few of the ones we hope to check out the next time we visit.

Highgate Cemetery West Tours: The Highgate Cemetery is perhaps the most well known and most visited London cemetery – we’ve even included it as one of the best dark and unusual places to visit in London. But the cemetery is divided into two parts (east and west) and in order to access the west side, arguably the more famous and alluring side, you must take a tour…

Uncomfortable Art Tours: Okay, so these aren’t really walking tours, but we love the concept of them so much we’re including them anyway. The Idea behind Uncomfortable Art Tours is to confront spaces of heritage (i.e. museums) and question (a) how these items are displayed – are there sexist or racist overtones in the wording, for example? and (b) discuss what right we even have to these items. So much of museums were looted from other cultures during colonial rule. Do we have a right to keep these items?

Gangster London Walking Tour with Actor Vas Blackwood: Explore London’s criminal underbelly with actor Vas Blackwood. Vas is known for his role as Rory Breaker in Lock, Stock and Two Smoking Barrels, a role that enabled him to get to know many high profile real-life criminals. This London walking tour takes you to several sites associated with the Krays, and sheds light on what it’s like to be a gangster in London.

Grim Reaper London Walking Tour: This seems like a mix of the Jack the Ripper walking tours and the Dark Side of London Walking Tour. You are taken around various macabre sites in London while I guide unravels the dark pasts associated with them. Nevertheless, this top rated tour seems to cover new ground not talked about in the others, so we’re still keen to give it a try!

Black History Walks: Black history is an aspect of British history not often talked about, or learned properly in schools. These London walking tours look to rectify that by exploring places and discussing events associated with Black history and movements within the city (and Britain in general). Although certainly the history here isn’t all dark, I think we can all agree it isn’t all sunshine and roses, either. We definitely think these will be incredibly eye-opening and look forward to visiting on our next trip!

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Do you enjoy walking tours? What about them do you like? Are you more into theatrics or history? Any other London walking tours you recommend for us?

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