08 Apr 2023

A walk through time: Five must-see historic buildings in The Rocks

The Rocks is one of Australia’s most intriguing historic sites. Discover five buildings that tell the fascinating tales of the precinct’s storied past.
A walk through time: Five must-see historic buildings in The Rocks


When the First Fleet landed on 26 January 1788 they arrived at a rocky peninsular on the Western Side of Sydney Cove. They called it The Rocks. Over the next several hundred years the area welcomed Sydney’s first prison, hospital, dockyard and bakehouse. Then, slowly, housing spread over the ridge and The Rocks became one of the busiest, most vibrant little precincts in Australia. Today if you visit the area you can travel back in time to the early days of colonisation, witnessing centuries of history in the precinct’s beautifully preserved buildings.

The Doss House

The Doss House at 77/79 George St is now a swanky subterranean whiskey bar, that serves fine drams, cocktails and gourmet bites in luxury surrounds. But the building it occupies wasn’t always so salubrious. The golden, 1840s sandstone walls could tell a colourful story or two - they’ve been home to a boot maker, boarding house, doctor’s surgery and even an opium dealer. In fact, if you look around you may still be able to see signs of the building’s intriguing past, hidden in plain sight.

Sergeant Lok

127 George Street is an imposing sandstone building with thick columns and ornate detailing in which Sergeant Lok serves elevated Asian fusion cuisine and serious cocktails. It’s the perfect spot for a fun night out, but visitors to 127 didn’t always have such a good time. In the late 1800s this building was a police station in the infamous Little Canton Area. The dining rooms, kitchens and cocktail nooks may look and feel luxurious now but they were once holding cells, change rooms, muster rooms and police offices!

Hickson House

One of Australia’s finest gin distilleries and cocktail bars operates out of Hickson House today, but centuries ago it was used for a different purpose. Back then a business owner called John Upward took a fifty year lease on the land and built a warehouse out of red brick and timber. This was a ‘bond store’ where goods that had import or export duties yet to be paid were stored. In 1972 the Metcalf bond stores were then redeveloped and tenanted by Pancakes in The Rocks and a spaghetti factory before Hickson House Gin Distillery arrived in 2022.

Fortune of War

In 1800 Samuel Terry was convicted of stealing 400 stockings and transported to Australia. After his sentence was finished Terry became an innkeeper, and in 1828 he built the Fortune of War, which is now the oldest continuously licensed public hotel in Sydney. During the war years it was known as the first and last stop of soldiers going to battle to experience the ‘fortune of war’. Members of the 2nd Mountain Battery have met every ANZAC Day in the Fortune of War since 1948.

Daintree Sydney and The Keel

Today 106 George Street in The Rocks is home to two cocktail bars, Daintree Sydney and The Keel. They both focus on using native ingredients and donate 50% of their profits to support reforestation and returning Australia's rainforests back to the indigenous people.

When the structure was built in 1860, it also served a benevolent purpose - to elevate the living conditions of working sailors by providing them a clean, inexpensive home when they were ashore in Sydney.