Paddington is one of kind and its history is as rich as it is colourful. Once possessing silent streams, rocky groves and walking tracks for Sydney’s ancient Indigenous peoples, Paddington began its colonial life in the first half of the 19th century with Australia’s first legal distillery: producing rum and gin. By the 1850s a small village had emerged  adorned charming sandstone stone cottages, windmills and simple churches.

Fast forward only a few decades to the 1890s and the Paddington Council  possessed more houses than any other  in Australia. A labyrinth of laneways, streets and squares had been forged from its rocky slopes to create a bustling suburb that was uniquely grand and Victorian to the core.

Row upon row of elegant terrace houses, each decorated with distinct iron laced balconies and pediments a lined every avenue, while on almost every street corner could be heard the hearty merriment of local pubs. Steam powered trams rattled past the finely groomed horses of handsome cabs. Industrious quarrymen, carpenters, bricklayers and stonemasons could be found busying themselves on every block as a seemingly infinite supply of residential construction continued to squeeze in stylish houses for an ever growing population.

…and then the crash. How dramatically things would change by the turn of the 20th century as the Federation Drought Depression brought wealthy inner city suburbs like Paddington to a standstill and resulted in the sudden exodus of the well-to-do residents that had installed their their mantle-pieces with marble and fitted their staircases with cedar.

By 1920 a Sydney health inspector would report that Paddington’s streets were the “worst place to live I have ever seen” and that poverty stricken tenants who inhabited these “disgusting slums” should “shoot their landlord” as they would “be better off in gaol than in these places”.

Luckily, and not without a fight, the very houses, pubs and avenues that once fell from grace during the dark days of Paddington’s past have been beautifully repaired and restored to their former glory — allowing our historical journey through this extraordinarily suburb to reflect and reminisce on all they’ve seen.

The Paddington we know today is a chic and sophisticated inner city suburb with elegant rows of terrace houses, charming cafes, lively pubs and boutique shopping. 

But rewind less than a century and you’ll find yourself in a very different world. A world of crime, murder, slums, sly-grog, burglary, gambling, rats, snakes, sewers, mysteries, misfits, hold-ups, drugs, raids, riots and revenge.

While the old-fashioned streets of Paddington remain much as they once were many generations ago, this tour revisits the rags that came before the recent riches.  Delving into the forgotten lives of its former residents, we’ll dig up tales of vice and villainy that played out between the 1890s and the 1960s. 

These were times when struggling tenants squished into decaying Victorian villas. Strange and sinister stories brewed behind closed doors and inside corner pubs. And newspaper articles summed up Paddington’s place in Sydney with shocking titles such as:

• “The House of Death”
• “Chased with an Axe” 
• “I stabbed her — I love her”
• “Double killing at drink party”
• “Men drugged and robbed in Kate Leigh’s house”
• “Squealing rats and rolling tins”
• “Two-up school in disused bakery”
• “A mystery of spontaneous combustion”
• “The pangs of poverty”
• “The plague in Paddington”
• “The Oxford Street Python”
• “An old friend of Ned Kelly”
• “Thieves’ amazing climb” 
• “The Kid Bandit robs again”

…and many, many more.