Sydney’s top 10 historic haunts

(c) James Tracy

SYDNEY comes with a storied past. In the hidden alleys and dens of the city’s inner streets, an assortment of artists, criminals, strippers, activists and hookers have all led their varied lives.

This is a town that lived by its own notorious anarchy and rum-induced monopoly during colonization, which later evolved into a place of street gangs, brothels and unsolved murders.

But Sydney’s history also involves beatniks, underground writers, artists and secret societies.

Taking a look back, let’s bring a few characters back to life — take a journey into their haunts and tell their colourful tales of mischief.

1. Hero of Waterloo, The Rocks

One of Sydney’s oldest pubs, the Hero of Waterloo was the popular drinking spot for the 1840s Garrison troops from colonial days.

Rum smugglers also favoured the convict-built hotel, using the tunnel that runs from the hotel’s cellars to the harbour to smuggle their goods.

But the tunnel also had another use: recruiting unknowing young men to work as sailors.

Legend has it that a man might find himself drunk at the bar, dropped through the trap door into the cellar, dragged through the tunnel, to awake next morning at sea shanghaied aboard a clipper.

Hero of Waterloo, 81 Lower Fort Street, The Rocks. Open Phone: (02) 9252 4553.

(c) Patrick Bingham-Hall

2. Elizabeth Bay House, Elizabeth Bay

No doubt some grand affairs were held in Elizabeth Bay House when it was first built and dubbed the “finest house in the colony” in the 1830s.

But a century later, this Regency-style, harbour-side property hosted parties of a different sort.

From 1928-1935, it was a bohemian artists’ squat and the popular haunt of artists like Wallace Thornton and Wolfgang Cardamatis.

By the 1940s, it was converted into 16-bed-sit flat where artist Donald Friend once stayed and sketched a wild party with uniformed guests sliding down the banisters.

These days, however, it has a more sedate purpose and is opened to the public as a museum.

Elizabeth Bay House, 7 Onslow Avenue, Elizabeth Bay. Open Friday, Saturday & Sunday 9.30am-4pm. See Phone: (02) 9356 3022.

(c) Mosman Council

3. Curlew Camp, Mosman

Below today’s Taronga Zoo, on the eastern shore of Little Sirius Cove, flourished an artists’ camp in the early 1880s.

Known as Curlew Camp, Australian artists Arthur Streeton and Tom Roberts were among those who pitched camp there to create some of their most famous paintings.

They reportedly had about a dozen tents between them, which included a dining tent, a dance floor and even a small piano.

Visitors can now retrace the artists’ footsteps as part of Mosman Council’s Curlew Camp Artists Walk.  which extends from the South Mosman ferry wharf and continues along to Taronga Zoo ferry wharf retracing the route the artists’ footsteps.

Curlew Camp Artists’ Walk, Mosman Council, enquiries: (02) 9978 4000.

(c) SHFA

4. The Suez Canal, The Rocks

Harrington Lane, now commonly called The Suez Canal (apparently a pun on “sewers”), was the reputed stomping ground of the notorious Rocks Push, a street gang that dominated The Rocks’ in the 1870s.

A mix of ex-convicts, riffraff and whores, they battled rival gangs for turf, frequented the local brothels and opium den, and engaged in fringe crime. Drunken sailors often fell prey to their schemes, lured back by female members to the lane, where they were assaulted and robbed.

Demolitions in the early 1900s largely put an end to gang’s back alley antics, but the Suez Canal still remains.

Suez Canal runs between George and Harrington Street. For more information, go to

(c) Daniel Allam

5.  The Royal George, now the Slip Inn

The Royal George on Sussex, now the Slip Inn (where Princess Mary of Denmark famously met her prince), once served as the favoured hangout to the left-wing, 1950s subculture called the Sydney Push.

In the pub’s upstairs back room, the tribe of writers, poets, intellectuals and academics gathered — often caricatured as a club for “talking, drinking and fornicating”.

Famous Push included Germaine Greer, Robert Hughs, journalists Liz Fells and Wendy Bacon and philosophers Jim Baker and David Armstrong.

The Slip Inn, once the Royal George, 111 Sussex Street, Sydney. Open Mon-Thu 12pm-12am; Fri 12pm-4am; Sat 5pm-4am; also open Sun. Phone: (02) 8295 9999.

(c) Sydney Council

6. Frog Hallow Reserve, Surry Hills

Today, the only remnants left of Frog Hollow is a quaint, little park, dotted with trees and manicured gardens, on the corner of Albion and Riley Streets.

But up until the 1920s, the site was Sydney’s worst slum and served as the underworld headquarters to some of the city’s most undesirables.

Notable characters included Samuel “Jewey” Freeman, the leader of the notorious Riley Street Gang, who plotted robberies and murders, and feuded with the other razor gangs of the time.

Legendary crime boss, Kate Leigh, also called it home, making her mark as the “queen of sly grog”.

The Frog Hollow slum was eventually demolished and slowly converted into parkland where it recently received a makeover courtesy of Sydney Council.

(c) Empire Hotel

7.  The Empire Hotel, Kings Cross

If only walls could talk, it begs to wonder what would be revealed at The Empire Hotel in Kings Cross.

Back in the day, it was called The Carousel Caberet, a transvestite nightclub owned by crime boss and “Mr Sin” Abe Saffron.

It was also the place where journalist and store heiress Juanita Nielson vanished in 1975.

Many accused Saffron for playing some part in her disappearance. But more than 30 years later, the crime remains a mystery.

The Empire Hotel, 32 Darlinghurst Road, Kings Cross. Open every day from 10am. Visit Phone: (02) 9360 7531.

(c) Brett Whiteley Studio

8. Brett Whiteley Studio, Surry Hills

“The fine art of painting, which is the bastard of alchemy, always has been always will be, a game,” said the late artist Brett Whiteley, whose singular genius can still be seen at the Brett Whiteley Studio in Surry Hills.

The converted T-shirt factory where he once lived and worked, up until his death of a methodone overdose in 1992, remains largely as he had left it.

A sprawling canvas depicting surreal, female bodies lazing on Bondi Beach sits to one side of his workspace, unfinished. While the graffiti-covered walls are lined with quotes, scribbled drawings, postcards and photos of his heros, including Bob Dylan and Francis Bacon.

The furniture, lighting, collections of memorabilia, postcards, photographs, objects etc., are all as he arranged them. The music that is played at the Studio during opening hours is from Brett’s collection.

Brett Whiteley Studio, 2 Raper Street, Surry Hills. Open 10am-4pm Saturday and Sunday. Entry free. See Phone (02) 9225 1740.

(c) Chantal Abitbol

9.  East Village Hotel, Darlinghurst

Forget about the Ibrahim brothers. They’ve got nothing on the razor gangs, which dominated Sydney’s crime scene in the 1920s and hung out at the Tradesmen’s Arms, the notorious “blood house” now the East Village Hotel.

Madams Kate Leigh and Tilly Devine held court over the two major gangs, whose preferred weapons were razors to inflict disfiguring scars.

Devine was said to have gone to the pub most of her life as her some 30 brothels were just a few blocks away on Palmer Street.

East Village Hotel, 234 Palmer Street, Darlinghurst. Phone: (02) 9331 5457. Contact:

(c) Chantal Abitbol

10.  Yellow Bistro and Food Store, Potts Point

The façade remains a bright, canary yellow. But that’s pretty much all that remains of the Yellow House that became a 1970s, conceptual art space where well-known artists such as Brett Whiteley and George Gittoes came to hang out.

Started up by artist Martin Sharp, it became a canvas and a piece of living art, with almost every wall, floor and ceiling covered in art.

Now a bistro and food store, the house was then known as Australia’s first “24 hour-a-day happening”, with art.

Yellow Bistro and Food Store, 57 Macleay Street, Potts Point NSW 2011. Phone: (02) 9357 3400.

This article originally appeared on CNNGo here.


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