Sydney: Convicts, Plague & Rebellion — The Rocks

Now, before you go inside, look down at your feet. The pavement out front is embedded with brass plaques marking the original shoreline of Sydney Cove. The harbour once lapped right up to where you're standing. All of Circular Quay is reclaimed land, built out over decades as the colony grew hungrier for wharf space.

Step inside — it's free — and head straight to the ground floor. Look down through the glass floor panels and you'll see a massive one-tonne scale model of the Sydney CBD, four point two metres by nine point five metres, built by a company called Modelcraft in nineteen ninety-eight. Every skyscraper, every park, every laneway, rendered in tiny detail. It's genuinely mesmerising, and it'll give you a bird's-eye orientation of the city before we disappear into the laneways of The Rocks.

The building stopped being a working customs house in nineteen ninety, and the City of Sydney took over in nineteen ninety-four, eventually turning it into the gorgeous public library and exhibition space you see today after a major refurbishment in two thousand and three.

Right, head out the front door, turn right, and walk northwest along Circular Quay West. Follow the waterfront promenade past the ferry wharves. You're heading for the oldest surviving residential building in central Sydney — and it's not where the water is anymore.

The cottage gets its name from John Cadman, and his story is properly wild. Cadman arrived in Sydney in seventeen ninety-eight aboard the convict transport ship Barwell, sentenced for the crime of stealing a horse. Despite starting life in the colony in chains, he worked his way up, joined the government boats by eighteen oh six, received a full pardon in eighteen twenty-one, and was appointed government coxswain in eighteen twenty-seven. He lived here with his wife Elizabeth until he retired in eighteen forty-five. A convicted horse thief who became one of the colony's most respected public servants — that's a very Rocks story.

After Cadman left, the building became the headquarters of the Sydney Water Police from eighteen forty-five to eighteen sixty-four, then the Sailors' Home from eighteen sixty-five all the way to nineteen seventy. Imagine the stories those walls absorbed — convicts, cops, and drunken sailors across one hundred and fifty years.

Today it's managed by the National Parks and Wildlife Service. Have a look at the brass plaque on the front wall, and notice the beautiful hand-cut sandstone blocks. Georgian architecture at its most unpretentious.

Now, head south along George Street. Walk about one hundred metres and you'll reach number one thirty-seven, where a very old pub is waiting for you.

The building you're standing in isn't the original — the current structure dates from nineteen twenty-two, designed by the Tooth and Co brewery's in-house architect. But the licence has been continuous since eighteen twenty-eight, which is what gives it the title. The Lord Nelson in Millers Point, built in eighteen thirty-five, claims to be the oldest pub building, but the Fortune of War has the older licence, and in pub arguments, the licence wins.

During both World Wars, this was famously the "first and last stop ashore" for soldiers and sailors heading to or returning from service. The walls were thick with cigarette smoke and tall tales.

If you're hungry, the pub now has a bistro called Bistro Eighteen Twenty-Eight serving solid pub grub with a bit of polish. For a proper schooner of something local, you can't go wrong. If you'd rather save your appetite, Pancakes on the Rocks is just around the corner on Playfair Street — it's been a Sydney institution since nineteen seventy-five, famous for late-night stacks and ribs. Open until midnight most nights, two a.m. on weekends.

Right, finish your drink and head out. Walk south along George Street, then duck into the narrow laneway on your right. You're looking for Nurses Walk.

Imagine the conditions. No antiseptic, no anaesthetic, no running water. The "nurses" were mostly convict women with zero medical training, working with only what had been brought out on the ships. Their supplies were pitiful. John White himself wrote that medicines were in such short supply they had to improvise constantly. The nurses would walk this very path — from George Street through to Harrington Street — carrying water, linens, and whatever herbal remedies they could cobble together. This laneway follows their route, and it was renamed Nurses Walk in the nineteen seventies as a tribute to those women.

Just through the archway beside the old police station at one twenty-seven George Street, you'll find Surgeons Court, the exact site where those portable hospital tents stood. There's a plaque on the wall commemorating the location. The first bakehouse in the colony was also established nearby — because feeding the sick was almost as urgent as treating them. Flour, water, and a brick oven. The basics of survival.

The tent hospital operated here until around eighteen sixteen, when a proper hospital building was finally constructed elsewhere. By then, thousands of patients had passed through. Many didn't leave.

Take a moment in the quiet of this laneway. It's a pocket of calm you wouldn't expect this close to Circular Quay. Then continue through to Harrington Street and look for a very narrow passage heading north. You're about to walk through Sydney's most infamous alley.

But it wasn't just the smell that made this place dangerous. From the eighteen seventies to the end of the eighteen nineties, this was the territory of the Rocks Push, one of Sydney's most notorious street gangs. These were larrikins — young, violent men who dressed in a very specific uniform: black bell-bottomed trousers, short black paget coats, white collarless shirts, gaudy neckerchiefs at the throat, and high-heeled boots with coloured stitching down the sides. Their leadership was decided by bare-knuckle boxing. The gang's female members would lure drunk sailors into the dark lanes — Suez Canal was a favourite — where the men would be beaten and robbed. Women were warned never to walk through here alone. There were stories of kidnappings and forced labour in brothels.

The lane was also home to opium dens and sly grog shops — unlicensed bars selling bootleg liquor. If you wanted trouble in nineteenth-century Sydney, Suez Canal would find it for you.

Remarkably, this laneway survived the mass demolitions that followed the bubonic plague outbreak of nineteen hundred, when the government tore down hundreds of buildings across The Rocks in the name of public health. Most of the surrounding streets were gutted, but this narrow corridor persisted.

Today it's lined with artisan shops and small galleries, and you'll probably share it with tourists taking photos of the sandstone walls. Quite the glow-up.

Continue north through the laneway and head uphill. You're heading for Foundation Park, where the plague story gets real.

Then came the plague. In January nineteen hundred, a delivery man named Arthur Paine became Sydney's first confirmed case of bubonic plague. He worked at Central Wharf, where ships carrying plague-infected rats had docked. Within eight months, three hundred and three cases were reported and one hundred and three people died. The government declared quarantine zones across The Rocks, Millers Point, and Darling Harbour, sealing them off with barriers and armed guards.

What followed was brutal. The newly formed Plague Department launched what they called "cleansing operations." Houses were doused in carbolic acid and lime chloride. Nearly fifty-three thousand metric tonnes of rubbish was dumped at sea or burned. The government paid two pence per dead rat, and over one hundred and eight thousand rats were killed by officials alone. But here's the political twist — despite only three of the one hundred and three plague deaths being traced to The Rocks, the government used the crisis to justify mass demolitions of the area. Hundreds of buildings were torn down over the next decade.

The houses whose foundations you're standing on were eventually demolished in the nineteen forties as part of that ongoing programme. The park was created in nineteen seventy-two, preserving these foundations as a memorial to how ordinary people lived — and how easily their homes could be erased.

Walk a short distance north along Gloucester Street and take the first right. Sydney's shortest street is waiting.

Now, here's a detail most walking tours skip. Before this street was a quaint heritage precinct, it was at the centre of Sydney's whaling industry. Warehouses along Atherden Street stored whale oil produced from butchering whales that were processed nearby. The stench of rendered blubber would have been overpowering. When you look at these pretty terraces with their iron lace and neat sandstone, remember that the neighbourhood once reeked of dead whale.

These buildings survived the plague demolitions and nearly didn't survive the nineteen seventies. In nineteen seventy-one, the New South Wales government announced plans to flatten most of The Rocks — including these terraces — and replace the neighbourhood with office towers and expressways. The residents formed the Rocks Resident Action Group and, after a year of futile petitions, turned to the New South Wales Builders Labourers Federation, led by Jack Mundey. The BLF placed a green ban on The Rocks — essentially, construction workers refused to demolish the buildings. In October nineteen seventy-three, residents and union members literally barricaded a demolition site on nearby Playfair Street, climbing onto rooftops and into trees. Fifty-four protesters were arrested, including Mundey himself. But the ban held from nineteen seventy-one to nineteen seventy-five, and these terraces — along with most of The Rocks — were saved. Construction workers saving heritage buildings by refusing to build. You have to love that.

Take a moment to appreciate the ironwork and the sandstone, then head back to Argyle Street and turn left. Walk downhill until the street disappears into solid rock.

The beautiful Italianate sandstone building behind you is the Sydney Observatory, built between eighteen fifty-seven and eighteen fifty-nine. It was established at the instigation of Governor Sir William Denison, who chose this location specifically because of its elevation. The building was designed by William Weaver and built under the supervision of Alexander Dawson.

Now, the best bit. See that tower with the ball on top? Every single day at exactly one p.m., that ball drops. It's been doing this since the fifth of June, eighteen fifty-eight. The purpose was beautifully practical — ships in the harbour needed to calibrate their chronometers for accurate navigation, and the time ball gave them a visible signal they could set their clocks by. When the ball dropped, a cannon at Dawes Point was fired simultaneously so you could hear it even if you couldn't see it. The cannon was later moved to Fort Denison, that small island you can see out in the harbour. One p.m., every day, boom. If you're here around that time, stick around and watch.

The Observatory operated as a working astronomical and meteorological station for decades, tracking weather patterns, mapping stars, and recording seismic activity. Today it's a museum — free to visit — with telescopes you can peer through on evening tours.

Spread a picnic blanket on the grass here if you have time. The jacaranda trees are spectacular in October and November, turning the hill purple. And if you want a proper sit-down meal after the walk, head back down to The Rocks — Izakaya Mitto on George Street serves refined Japanese food in a restored eighteen nineties heritage building, or grab a harbourside table at the Gantry at Pier One for seafood with a view of the bridge.

That's your walk through The Rocks — convicts, plague, gang warfare, demolition protests, and some of the finest sandstone architecture in Australia. Every cobblestone has a story. Cheers for walking it with me.