Stories in Stone: Exploring The Rocks’ Historic Landmarks

The Argyle Cut: Sydney’s Rock-Carved Gateway

Before the mid-nineteenth century, Argyle Street was split in two, separated by a towering ridge of sandstone. Anyone wanting to travel between The Rocks and Millers Point had to make a lengthy detour around the waterfront—unless they dared to scramble across the rocky barrier.

Calls for a direct route came early in the colony’s history, but it wasn’t until 1842 that convict chain gangs began hacking into the stone with crude picks. The task proved too much, and the work was abandoned until the Sydney City Council took over in 1859, using explosives to blast through the rock. The sandstone debris filled parts of Circular Quay and reshaped the foreshore, linking the Cut to other feats of early engineering such as Busby’s Bore and Fort Denison.

Over the decades, new bridges reunited severed streets above the Cut, while later roadworks widened the opening to accommodate the growing city. The completion of the Bradfield Highway in 1932—giving access to the Sydney Harbour Bridge—cemented the Argyle Cut’s role as one of Sydney’s most significant engineering achievements. Today, its dramatic sandstone walls remain an imposing reminder of the challenges early Sydney faced in overcoming its natural landscape.

The ASN Hotel: Tales of Tricksters and Ties to America

On the corner of George and Argyle Streets once stood the New York Hotel, a pub operating since 1839. By 1891 it had been replaced by a new building and a new name—the ASN Hotel, after the Australasian Steam Navigation Company whose monumental offices still stand nearby.

The ASN quickly became part of The Rocks’ colourful character. In 1902, it was the scene of an elaborate robbery when two well-dressed tricksters faked a medical emergency, distracting the publican long enough to steal £40 from under his pillow. Although one man was arrested, he denied ever staying at the ASN and later attempted to sue for damages, turning the saga into a legal spectacle.

Under licensee Harvey Taft (a cousin of U.S. President William Howard Taft), the pub was said to double as the American Consulate. But it wasn’t all diplomacy—its location near the wharves made it a flashpoint for tension. In 1907, a brawl linked to union disputes saw a local tailor assaulted and the courts embroiled in conflicting testimony.

Despite its lively reputation, the ASN Hotel was also a family place, with the Taft family living upstairs and running the venue until 1916. Though the pub is gone, the stories remain—reflecting The Rocks’ role as a hub of maritime, social, and political life.

The Australian Hotel: Built to Last

The Australian Hotel has been a cornerstone of The Rocks for more than a century. The original hotel, leased to John Murray, once stood on Cumberland Street but was demolished in 1907 as part of government plans to realign the road. Refusing to give up, Murray successfully lobbied for a new site at the corner of Cumberland and Gloucester Streets.

In 1912 he was granted a fresh lease, and by 1914 a two-storey hotel with a cellar and adjoining shops stood proudly on its new foundations. Since then, the Australian has cemented itself as a true Sydney institution—welcoming generations of locals, sailors, and visitors with good food, live music, and games of two-up.

Still trading today, the Australian Hotel embodies both resilience and continuity: a place that has adapted to the times while keeping its role as one of Sydney’s great gathering places.

The Orient Hotel: A Living Piece of History

The Orient Hotel, occupying its prominent corner on George and Argyle Streets, is one of Sydney’s oldest surviving pubs. Built as a private residence around 1842, it became licensed premises in 1851 under the name Marine Hotel before adopting the name we know today. This early conversion of a home into a pub was common in the colony, but few examples remain in continuous operation like the Orient.

The hotel’s Colonial Georgian character, later complemented by sympathetic Federation details, makes it a standout in The Rocks’ heritage streetscape. Its history is tied to notable figures such as merchant Mary Reiby, solicitor Frederick Wright Unwin, and brewing powerhouse Tooth & Co. Beyond its architecture, the site may also conceal archaeological links to the area’s convict hospital, offering research potential into Sydney’s earliest years.

Over its long life, the Orient has reflected changing social and legal trends. Parlours and accommodation once formed part of the business, but by the late 20th century its focus shifted to community, dining, and tourism—helped by conservation works in the 1970s that emphasised its Georgian streetscape character.

Listed on the NSW State Heritage Register in 2002, the Orient continues to thrive as both a historic landmark and a popular gathering place. It embodies the resilience of Sydney’s pub culture and remains one of The Rocks’ most enduring meeting spots.

Gannon House: From Shelter to Showcase

Behind the sandstone façade at 45 Argyle Street lies one of The Rocks’ most quietly remarkable stories. Built in 1839, this two-storey building has witnessed almost two centuries of change, its walls carrying the imprint of those who lived, worked, and found refuge within. In 1935, during the difficult years of the Great Depression, Susan Francis transformed the property into a women’s hostel. For over four decades, four generations of her family provided food, shelter, and support to vulnerable women and girls, turning the house into a lifeline for those with nowhere else to go.

As Sydney evolved, so too did the uses of the building. It became home to a marine conservationist, a bookshop, a specialist map and print dealer, and even wine cellars. Each new chapter reflected the shifting needs and interests of the community, while the sandstone walls stood as steadfast witnesses to change.

Most recently, the property became Gannon House Gallery, a celebrated space dedicated to showcasing contemporary and Indigenous Australian art. Here, creativity replaced survival as the central theme, allowing visitors to engage with stories told through painting, sculpture, and design—all while preserving the heritage of the building itself. Gannon House remains proof that The Rocks’ past is never static, but continually reimagined through the lives it touches.

On the corner of Atherden and Playfair Streets stands a row of Playfair Terraces, dating back to the days of Alderman Thomas Playfair—a prominent butcher who supplied meat to Sydney’s maritime industry. These modest terraces, built in the 19th century, once housed workers tied to the bustling trade of the waterfront.

In the 1970s, the terraces were still standing as echoes of an older way of life. Today, they remain part of The Rocks’ unique fabric, but with a new twist: every Wednesday evening, the laneway transforms into an open-air cinema. Visitors lounge on bean bags under the stars, enjoy popcorn, and sip refreshing drinks from Hickson House, keeping the tradition of community gathering alive in a thoroughly modern way.

On the corner of Argyle and Harrington Streets sits the Endeavour Tap Rooms, once known as the British Seaman’s Hotel in 1922. This spot has long offered refreshment to locals and travellers, but today it combines history with craft flair.

Inside, you’ll find a working brewery, bar, and restaurant serving up NSW wines on tap and seasonal cocktails alongside a menu famous for its smoked produce. With seating spilling onto the cobblestones, the Tap Rooms are a place where history meets hospitality—proof that The Rocks’ long tradition of good pubs and good company is alive and well.

Living Heritage

Together, these landmarks—the Argyle Cut, ASN Hotel, Australian Hotel, Orient Hotel, Gannon House Gallery, Playfair Terraces, and Endeavour Tap Rooms—capture the spirit of The Rocks as a place where Sydney’s past is not only preserved but still lived and enjoyed. Whether it’s the dramatic sandstone passageways carved by convicts, the rowdy tales of waterfront pubs, or the evolving uses of terrace houses and galleries, The Rocks offers a rare chance to step back in time while standing at the heart of a modern city.