We can all probably imagine a link between gangsters and brothels, but where do lolly shops fit in the equation?
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Well, once upon a time, in inner city Melbourne, just a street over from the police precinct, organised crime was rife in the area surrounding Little Lonsdale St, otherwise known as ‘Little Lon’, the slums or the red-light district.
Sly grog was slung under counters at tobacco shops that sellers had opened as a cover.
Lolly shops were a front for illegal brothels.
It’s amusingly ironic that these pairings from the late 1800s and early 1900s made way for a world where, in 2026, lolly shops are being opened as a smokescreen for illegal tobacco to be sold under their counters, when tobacco itself used to be the cover for other illegal activity.
Sugar, as poisonous as it is, has clearly never been an issue for the authorities; therefore a brilliant decoy that has stood the test of time.
I learnt so much about Melbourne’s past in streets I’d walked down many times before, but had never realised I was treading the same path notorious gangster Squizzy Taylor and brothel boss Madame Brussels once did, when I joined a walking history tour in Melbourne earlier this year.
The tour was run by Melbourne Historical Crime Tours.
The company’s owner, historian and author Michael Shelford, was our guide.
We met at the historic Coopers Inn pub on the corner of Exhibition and Little Lonsdale Sts.
The juicy historical stories started streaming out of Michael’s mouth immediately and did not stop for the duration of the two-hour tour.
As we made our way down Little Lonsdale St, he told us stories of the late 19th- and early 20th-century figures who characterised the block, including gangsters, madams, sly grog sellers, corrupt cops, missionaries, various other criminals and the patrons of the sly grog shops and brothels, among whom were royal figures, perhaps unsurprisingly.
He pointed out former brothels and grog shops, the first Jewish synagogue in the area, the ragged boys’ school, a kindergarten for children of the slums, residences of gangsters, before leading us inside the last remaining single-storey cottage from the era, which is now a tiny gin distillery.
We stood before the largest olive tree I’d ever seen, planted on the grounds of Wesley Church complex in 1875 by lay preacher Mr Mars Miller, which was apparently from a cutting brought from Jerusalem in 1839.
The modern building that had been built adjacent in more recent years was staggered backwards, a requirement for its construction that it did not block the sun from shining on the holy tree.
The church was a slum outreach centre when the surrounding red-light district turned into a poor and rough part of the city.
The tour was fascinating. And scandalous.
And given a good part of the original architecture of the time remains in place, paired with Michael’s vivid picture-painting with his scene-setting storytelling, I could really visualise the characters running amok right where I stood.
The crazy thing about wild historical stories is that we tend to glorify criminals.
If our neighbours were selling prohibited goods and providing illegal services, we’d frown upon them.
But 100 years from now, their story might be cemented in the history books, making true-crime lovers lick their lips before devouring it with satisfaction.
Look at Ned Kelly and his gang.
They’ve been romanticised as heroes, but essentially, they were cop killers and thieves.
Yet we made movies about them and got them tattooed on our skin and crafted letterboxes resembling their armour, as though we didn’t just condone law-breaking, we revered it.
And I guess that’s why I gobbled this tour up, too.
The older a story a gets, the more outlandish it can seem.
But Michael will bring it all to life in a way that makes it almost seen, so can be easily believed.
If you’ve got a spare couple of hours in Melbourne one day, I absolutely recommend taking a wander with him around ‘Little Lon’.