Melbourne Historical Walking Tour: Crime, Gangsters & Lolly Shops

Lolly shops, brothels and gangland names such as Squizzy Taylor make for an unexpected history lesson in central Melbourne. This two-hour walk links present-day streets with the city’s underworld from the 1870s to the 1930s, including the former Little Lon district.

I love two things about this tour: Michael’s research into old police records gives the stories a firm footing, and the booklet’s character photos help you keep track of the cast. You’ll also pass buildings whose former uses are hard to guess from the street today.

One consideration: this is a story-led walking tour, not a tasting experience. The Little Lon Distilling Co stop lasts about ten minutes, and food and drinks are not included.

At a glance

• A walk through Little Lon: Explore Melbourne’s CBD and its former underworld district.
• Gangsters and street life: Hear about crime mobs, brothels, speakeasies and Squizzy Taylor.
• Lolly shops with a darker role: Learn how candy stores served as fronts for drug operations.
• One historic cottage: Stop at Little Lon Distilling Co, housed in a surviving former cottage and brothel.
• A guide with archival research: Michael draws on old police files and provides a booklet with photographs.
• Two hours, with a small group: The tour lasts about two hours and is capped at 20 people.

A darker story behind Melbourne’s CBD

Melbourne’s central streets have several layers of history. On this walk, the focus is the less polished one: the people and businesses tied to crime, prostitution and sly-grog selling from the 1870s through the 1930s. The tour puts those stories into the streets where they unfolded, rather than leaving them as names in a book.

The area known as Little Lon is central to the experience. The district had a reputation for brothels and vice, and the tour follows its changing streetscape through stories of the people who lived and worked there. The modern city can make the past easy to miss, so having a guide point out the buildings and explain their former uses adds useful context.

I like that the tour treats the past as more than a parade of notorious criminals. It connects gangsters such as Squizzy Taylor with the businesses and neighbourhood life around them, including the unlikely role of lolly shops. Those details make the stories memorable without pretending that Melbourne’s past was all glamour and bravado.

Starting on Exhibition Street

The meeting point is 282 Exhibition Street, in Melbourne’s CBD. The walk finishes at 36 Lonsdale Street, at the corner of Lonsdale Street and Madame Brussels Lane. The two-hour format gives you time to hear a sequence of stories while seeing the district, rather than squeezing the subject into a quick overview.

The tour’s maximum group size is 20. That cap matters on a city walk: a smaller group is easier to keep together and makes it more practical to hear the guide while standing on a street. The exact route between the meeting point and each story stop is not specified, so think of this as a guided exploration of the area, not a fixed list of indoor attractions.

The guide associated with the tour is Michael Shelford. His own research into historical police records is a key part of the experience. That research helps ground colourful anecdotes in documentary material, a welcome balance when the subject includes myths and legends as well as real crime.

Little Lon, one cottage at a time

The named stop is Little Lon Distilling Co, a gin distillery operating from Melbourne CBD’s only surviving single-storey cottage. The cottage was once a house of ill repute, and Michael tells stories about its former inhabitants using information from original police files.

The stop is listed at about ten minutes, with admission included at no extra cost. That is enough time to focus on the building and its past, but not a long visit. If you are hoping to sample gin or linger inside, this tour does not promise that; it is built around history and storytelling, not tastings.

The cottage gives the walk a tangible anchor. A police file can tell you names and events, but standing beside a surviving building helps you picture the scale and setting of the neighbourhood. The contrast between the cottage’s past and the modern CBD around it is part of the appeal.

Gangsters, brothels and the lolly-shop connection

The tour covers crime mobs and gangsters active between the 1870s and the 1930s, including Squizzy Taylor. You’ll hear myths and legends associated with these figures, but the guide’s attention to police records helps give the stories a documented base. Expect lively characters and local detail, not a dry catalogue of dates.

Lonsdale Street and the old Little Lon district feature buildings once used as brothels and hubs for crime. The tour also explores the city’s former speakeasies and sly-grog trade. These stories help explain how Melbourne’s social life and criminal networks overlapped in a period when illicit businesses could operate behind ordinary-looking fronts.

The lolly-shop stories are a particularly good reason to take this walk. Candy stores might sound harmless, but the tour explains how they could serve as fronts for large drug operations. That surprising detail gives the title its point and makes the tour more than a standard gangster-history stroll.

Why the guide and booklet matter

This subject can easily slip into sensational tales, especially when famous names are involved. Michael’s research and measured presentation help keep the focus on the people, places and records behind the stories. The strongest part of the format is the combination of his narration with the buildings still present around you.

You receive a booklet featuring photographs of the people discussed along the way. That is a practical touch: the cast of a neighbourhood’s past can become difficult to follow when names, aliases and family connections come thick and fast. Having faces to refer to gives the stories a clearer shape and offers a useful keepsake after the walk.

The guiding style is a major part of the experience. Michael is described as engaging and well paced, and the walk is designed to leave room for questions. If you enjoy local history told through people rather than dates alone, that approach should suit you. If you prefer a quiet walk with minimal commentary, this is not the right format.

Is two hours worth $35.86?

At $35.86 per person, the value depends on how much you enjoy guided history. You are paying for two hours of interpretation, a small-group format capped at 20, the booklet, and access to stories that are not obvious from the street. The price is reasonable for someone who wants a focused introduction to Melbourne’s criminal past, especially with a guide whose research is central to the experience.

It is less compelling if you are mainly looking for a food or drink outing. Bring your own food and drinks, since they are not included, and don’t assume the cottage stop includes a tasting. One visitor wished there were more time to sample things at the historic cottages, which points to a useful distinction: this is a walking history tour, not a distillery tour.

At around two hours, the tour is also easy to fit into a city stay. The route begins and ends in the CBD, close to public transport. Confirmation is received at booking, and free cancellation is available up to 24 hours before the start time. Changes or cancellations inside that window are not accepted for a refund.

Who should book this walk?

I’d put this tour high on the list for anyone interested in Melbourne’s past, crime history or the stories behind familiar streets. It also suits locals: Little Lon’s history can add a fresh layer to a neighbourhood you may think you already know. The short duration and central location make it a manageable choice for a half-day plan.

You do not need to be a crime buff to enjoy it. The best stories connect notorious figures with the ordinary places around them, and the lolly-shop fronts are an unusual angle on the city’s past. Still, the subject matter is the draw. If you are not interested in old police cases, gangsters or brothel history, the two hours may feel talk-heavy.

Children must be accompanied by an adult. Service animals are allowed, and the activity information says most people can participate. The tour is near public transport, though you should be ready to walk for about two hours.

Should you book it?

Book this tour if you want a well-researched, story-led look at Melbourne’s underworld and enjoy seeing history tied to real streets and buildings. Michael’s police-file research, the character booklet and the Little Lon cottage give the experience substance beyond gangster folklore.

Skip it if you want a tasting, a broad survey of all Melbourne history, or a mostly indoor activity. For the right person, though, two hours in Little Lon offers a vivid way to understand the city’s less respectable past, and why an old lolly shop might have had more going on than sweets.

FAQ

How long is the Melbourne Historical Walking Tour?

The tour lasts about two hours.

How much does the tour cost?

The listed price is $35.86 per person.

Where does the tour start and finish?

It starts at 282 Exhibition Street, Melbourne, and ends at 36 Lonsdale Street, at the corner of Lonsdale Street and Madame Brussels Lane.

What is the tour about?

It explores Melbourne’s CBD underworld from the 1870s to the 1930s, including gangsters, crime mobs, brothels, speakeasies and the Little Lon district.

Who is the guide?

The guide associated with the tour is Michael Shelford.

How many people can join?

The tour has a maximum group size of 20 people.

What is included?

You receive a tour booklet with photographs of the people discussed. The Little Lon Distilling Co stop has no separate admission charge.

Are food and drinks included?

No. Bring your own food and drinks.

Can I cancel for a refund?

You can cancel at least 24 hours before the experience starts for a full refund. Cancellations and changes made less than 24 hours before the start time are not accepted.