Melbourne: Gangsters, Brothels and Lolly Shops Tour

In Little Lon, a confectionery shop could offer more than sweets and soft drinks. This two-hour walk follows the traces of Melbourne’s former slum and red-light district, where brothels, sly grog shops and drug dens operated from the 1850s to the 1940s. Writer and historian Michael Shelford leads the way with stories of the people behind these hidden-in-plain-sight addresses.

I like two things in particular: the focus on the women who ran the district and resisted gangsters, and the way the route connects those stories to actual lanes and buildings. You’ll also stop outside the former home of Squizzy Taylor and see Melbourne’s last remaining single-storey cottage in its back lanes.

One consideration: this is a compact walking tour with time spent listening at stops, rather than a long march across the city. If you prefer to keep moving, you may find the standing stretches a little slow. Wear comfortable shoes, and bring weather protection suited to the day.

Key points

• Little Lon’s lanes reveal the former slum and brothel district through the streets where its businesses once operated.
• The women of the area take a central role, including madams who stood up to gangsters and the all-female crime group known as The Combine.
• Squizzy Taylor’s former home gives the city’s best-known gangster story a specific address.
• Drug dens and late-night cafes help explain the district’s connections to opium and cocaine, not just brothels and sly grog.
• The last single-storey cottage offers a rare glimpse of the modest buildings that once filled Melbourne’s back lanes.
• Michael Shelford’s photo booklet provides pictures of the characters featured on the walk.

Little Lon, hiding in plain sight

This tour’s appeal lies in the gap between the city you see today and the one that occupied these lanes a century ago. Downtown Melbourne is easy to cross without noticing how much has changed, but the walk asks you to pause at ordinary-looking buildings and imagine their former use as brothels, sly grog shops or places where people gathered after dark.

The district known as Little Lon was a slum and red-light area from the 1850s through the 1940s. The tour’s subject is not simply a catalogue of illicit businesses. It looks at how the area worked, who held power there, and how the police and gangsters shaped daily life.

That context matters. A story about a brothel is more useful when it also tells you about the person who ran it, the people who used it and the pressures around it. Here, the women of Little Lon are not treated as background figures. Their decisions and struggles form one of the main threads of the walk.

The tour is also a good fit if you like history tied to place. You are not only hearing about an old address in a room or reading it on a plaque. You stand outside buildings and move through streets and alleys where the stories unfolded. The city has changed, of course, but those locations give the past a sharper outline.

The walk: former brothels, sly grog and back lanes

The group meets at 282 Exhibition Street, outside the Coopers Inn Hotel, and leaves at the stated start time. If you arrive late, the small paved park across the lane may help you spot the group, but it is best to be there before departure.

Over two hours, you explore downtown streets and lanes associated with Little Lon. The stops include buildings that were once known as houses of ill-fame, along with former sly grog shops. The tour links the buildings to stories of what happened inside them and on the surrounding streets.

The exact order of stops is not specified, so think of this as a guided route through a compact part of the city rather than a fixed sequence of attractions. One advantage is that you do not need to cover a great distance to encounter a lot of material. The short distances leave room for Shelford to explain the setting and characters at each stop.

That pace has a trade-off. You may spend more time standing and listening than walking, which suits anyone who wants detail and a comfortable route. If you prefer to keep a brisk stride, or want a strenuous walking tour, this may feel more like a series of outdoor talks than a workout. The good news is that the walk does not require you to hurry from one far-flung site to another.

As you go, look at the buildings as well as listening to the stories. The point is not to expect every location to look as it did in the past. Instead, the tour helps you understand how these sites once fit into the district, and why a lane or modest frontage could carry a very different reputation.

Women, gangsters and the fight for control

One of the strongest reasons to choose this tour is its focus on women who ran businesses in Little Lon. The story includes madams who stood their ground against well-known gangsters, including Squizzy Taylor, and an all-female crime syndicate called The Combine.

That focus gives the tour more than a parade of notorious men. You hear about power and conflict from the perspective of the people who operated within the district, rather than viewing them only through the lens of the police or the gangsters who became famous. The stories cover battles for supremacy and the ways women defended their interests.

The stop outside Squizzy Taylor’s former home is a useful point of contrast. Taylor is described as Australia’s most famous gangster, and seeing the address makes his story less abstract. The tour does not need a grand monument to bring the past close; a specific place, paired with a well-told account, can do the job.

Shelford’s delivery is a major part of the experience. His role as a writer and historian shows in the breadth of detail, and the stories are designed to keep the group engaged while covering shootings, bombings, bashings, robberies and police battles. The tone is lively, but the subject matter is often grim. Expect crime history, not a polished tale in which every character comes out well.

Opium dens, cocaine cafes and the old lolly shop

The title’s lolly shop is a playful way into a more complicated subject. The tour explores an era when a local confectionery store could be connected to a wider world of vice and illicit trade. That contrast between a familiar shopfront and the business behind it makes for a memorable theme without reducing the district to a novelty.

You will hear about former opium dens and all-night cocaine cafes, as well as the characters who frequented them. These stops broaden the picture beyond prostitution and gangland rivalry. Little Lon was a place where different kinds of businesses and social worlds met, including drug use and sly grog, the local term used here for speakeasies.

The tour’s appeal is partly in the odd details. A building that looks unremarkable now may have once served a very different crowd, and a confectionery shop could have a less innocent side than its name suggests. Shelford explains those connections through stories of the people and practices associated with the premises.

This is also a reminder to approach the subject with curiosity rather than expecting a single sensational reveal at every stop. Some parts of the route are best understood through the account attached to them, not through a dramatic-looking façade. The guide’s explanations are what turn the ordinary street into a historical setting.

The cottage and the value of looking closely

The tour includes Melbourne’s last remaining single-storey cottage in its back lanes. It is a small but telling detail in a walk that deals with a district often remembered for its crime and sex trade. The cottage gives you a look at the more modest building fabric of the lanes, and a sense of how much of that earlier city has disappeared.

This is the kind of stop that rewards attention. It may not have the scale of a major landmark, but its value comes from rarity and context. Once Shelford has explained how the back lanes were used, a surviving cottage becomes more than an old structure tucked away from the main streets.

A free booklet with photographs of the people featured on the tour is included. It helps put faces to the names and characters in the stories, and gives you something to refer to as the route moves between sites. Since this is a story-heavy walk, those images are a useful companion rather than a throwaway souvenir.

Michael Shelford’s storytelling and the pace

The guide is a central reason to book. Shelford is described as a writer and historian, and the tour draws on years of research about Melbourne’s past. His storytelling covers a wide range of subjects and leaves room for questions, so you can ask for clarification instead of simply following a memorized script.

The delivery is interactive, which is helpful when a tour has many names and incidents to hold in your head. You get more from the walk if you listen for how the stories connect: women’s businesses, gangland pressure, police attention and the district’s drug and drinking culture are all parts of the same place.

The pace is comfortable, and you do not have to walk far to reach the different sites. That makes the tour manageable if you want a history walk without a demanding route. But there is a fair amount of standing while the guide talks. If that is a concern, consider your comfort with two hours outdoors and bring appropriate clothing.

Local residents can get plenty from the tour, too. Familiar streets take on new meaning when you learn what operated in them a century ago. For first-time visitors, it offers a less conventional way to understand central Melbourne, beyond its better-known sights.

Is $35 good value?

At $35 per person, the tour offers two hours with a specialist guide, a focused route through Little Lon and a photo booklet. You are paying mainly for Shelford’s research and storytelling, not for admission to a series of indoor attractions. If you enjoy social history and want local context, that is a fair trade.

Value depends on what you want from a walking tour. If you measure it by distance covered or the number of major monuments entered, this may not be the best match. The route is compact, and much of the experience comes from listening to detailed accounts outside the buildings rather than going inside them.

If you like a guide who can make a city’s less obvious corners meaningful, the price is easier to justify. The subjects are specific, the time is well focused, and the stories connect several strands of Melbourne’s past. Keep in mind that one person who booked at the last minute felt a $50 price was high; the stated price here is $35, so check the amount shown when you book.

The tour is available in English, lasts two hours and is listed as wheelchair accessible. Wear comfortable shoes, and use sunscreen or weather protection according to conditions. The tour has free cancellation up to 24 hours in advance, and a reserve-now, pay-later option is available.

Who should book this Little Lon walk?

I would choose this tour if you are curious about crime history, women’s lives, old city neighbourhoods or the gap between Melbourne’s present streets and their former uses. It suits locals as well as visitors, and it is especially appealing if you want stories attached to real places rather than a broad overview of the city.

It is less suitable if you want a fast-paced walk, a long route or a tour focused on interiors and major landmarks. The subject matter includes sex work, drugs and violence, so it is also worth considering whether those themes are right for everyone in your group.

Book it for the stories and the guide, not for distance covered. If Little Lon’s hidden past sounds more interesting than another pass by familiar city sights, this is a practical, engaging way to spend two hours.

FAQ

How long is the tour?

The tour lasts two hours.

Where is the meeting point?

Meet at 282 Exhibition Street, outside the Coopers Inn Hotel. The group leaves at the starting time. If you are running late, look for the group in the small paved park across the lane.

What language is the tour in?

The live tour is in English.

Is the tour wheelchair accessible?

Yes, it is listed as wheelchair accessible.

What is included in the price?

A free tour booklet with photographs of the characters featured on the walk is included.

What should I wear or bring?

Wear comfortable walking shoes. Sunscreen and protection from the weather are recommended according to conditions.

Can I cancel the booking?

Yes. You can cancel up to 24 hours in advance for a full refund. A reserve-now, pay-later option is also available.