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 By 1891 it had been replaced by a new building and a new name—the ASN Hotel, after the Australasian Steam Navigation Company whose monumental offices still stand nearby.The ASN quickly became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.
Playfair Terraces: From Meat Trade to Movie Nights
On the corner of Atherden and Playfair Streets sits a row of terraces with a story as rich as The Rocks itself. Known as the Playfair Terraces, they date back to the 19th century and the era of Alderman Thomas Playfair, a well-regarded butcher and local politician. Playfair was a key supplier of meat to Sydney’s maritime industry, and these modest sandstone and brick homes were built to accommodate the workers who kept the waterfront’s trade moving.
By the 1970s, the terraces still stood as reminders of a working-class past, their narrow facades and close-knit design reflecting the simple but vital lives of those who lived there. Today, they form part of the treasured streetscape that makes The Rocks one of Sydney’s most atmospheric precincts, blending heritage character with contemporary life.
Each Wednesday evening in the warmer months, the terraces and surrounding laneway take on a new role as the backdrop for open-air cinema nights. Visitors stretch out on bean bags beneath the stars, nibbling popcorn and sipping cocktails or craft drinks from Hickson House Distilling Co. It’s a modern twist on the tradition of gathering in The Rocks—a place where stories of the past meet the vibrancy of the present.
Endeavour Tap Rooms: A Pub with a Brewing Past
On the bustling corner of Argyle and Harrington Streets stands the Endeavour Tap Rooms, a venue that continues The Rocks’ long tradition of hospitality. The site first poured drinks in 1922 as the British Seaman’s Hotel, a favourite stop for sailors, dock workers, and travellers seeking refreshment after long days on Sydney’s busy harbour. Its heritage façade still recalls that era, offering a glimpse into the precinct’s enduring pub culture.
Today, the Endeavour Tap Rooms reimagines that history with a distinctly modern twist. Step inside and you’ll discover a working brewery, bar, and restaurant where craft and creativity take centre stage. House-brewed beers flow alongside New South Wales wines on tap, seasonal cocktails, and an inventive food menu built around smoked meats, fresh seafood, and shared plates designed to linger over.
The atmosphere spills naturally onto the cobblestoned streets, with outdoor seating that invites you to settle in and soak up The Rocks’ vibrant character. Whether you’re a history enthusiast, a craft beer lover, or simply in search of a relaxed spot to meet friends, the Endeavour Tap Rooms captures the best of old and new—a place where heritage and hospitality come together in perfect harmony.