Australia’s biggest city is also the country’s oldest, and as long as Sydney has existed, its inhabitants have enjoyed a tipple. Pour yourself a schooner and raise a glass to these 10 historic Sydney pubs, dating back to the early 19th century. Cheers!
The Lord is proud of its title as Sydney’s oldest continually licensed hotel, pulling beers non-stop since 1841. A plasterer named William Wells converted his home into a three-storey sandstone hostel in the 1840s and the pub has remained in its original skin ever since, benefiting from significant renovations and the addition of a brewery in the 1980s and 90s. Today, the Lord serves a range of brews, plus modern Australian cuisine, and also offers accommodation.
Not far from the upmarket Lord is a pub with a more ‘colourful’ history that also claims to be the oldest hotel in Sydney, originally built by a former convict in 1828. Local brewery Tooth & Co rebuilt the rundown property in the 1920s, which challenges the ‘continuously licensed’ label, but that facelift doesn’t diminish the Fortune of War’s two centuries of history in the heart of the Rocks precinct, especially the strong ties to the Australian Armed Forces.
This pub began life on George St in 1824 before a plague outbreak in 1900 forced the government to tear down the building, and made the licensees shift their business to a site on nearby Cumberland St where the Australian Heritage Hotel remains today. Don’t miss the ‘Coat of Arms’ pizza — featuring kangaroo and emu meat — for a patriotic meal in this well-preserved Edwardian watering hole.
Named after the Duke of Wellington, this grand old sandstone pub has been an icon of Millers Point for more than 170 years. The heritage-listed Hero of Waterloo was built by convicts in the 1840s and has been described as Australia’s most haunted pub, thanks to the trapdoor used to shanghai sailors and the ghost of Anne Kirkman, the murdered wife of a former publican.
Yet another Rocks establishment with history stretching back to Sydney’s colonial era, this quaint pub is now dedicated to serving a selection of quality craft beers. The property was originally a private residence and has gone through many pairs of hands before being renovated into one of Sydney’s premier boutique beer venues, boasting 12 rotating taps, two hand pumps and brewery-fresh products from the Rocks Brewing Co in Alexandria.
Not all of Sydney’s historic pubs are located in the Rocks, and this Parramatta institution has been around since 1796. The Woolpack was originally founded in the late 18th Century as the Freemasons Arms Inn before being rebuilt across the road from its original location in the 1890s, then recently transforming into a contemporary bar complete with a trendy beer garden and a modern Thai restaurant.
Back in horse-and-cart days, travellers needed somewhere to stop for refreshment midway between Sydney and Parramatta — hence the foundation of the Half Way House Hotel on Parramatta Road in 1809. The pub was renamed the Britannia, the Homebush Inn, Abrahams Family Inn and Jockey Club Hotel, then survived a series of rebuilds to emerge as the modern Horse & Jockey Hotel, a local favourite featuring a sunny beer garden and family-friendly bistro.
The oldest pub on the Australian mainland is perched on the banks of the Hawkesbury River, a storied sandstone structure in Windsor, west of Sydney city. Built by an ex-convict under orders from Governor Lachlan Macquarie (who humbly named the place after himself), the Macquarie Arms Hotel is the oldest continually licensed pub on the Australian mainland, shaded only by a small handful of pubs in Tasmania.
Occupying its current site since 1860, the Rag is one of the most historic watering holes located north of the Sydney Harbour Bridge. This North Sydney institution began as a thatched-roof single-storey inn called the Sailors Return, before taking on a new name in 1866. As the skyscrapers of North Sydney have gradually sprung up around it, the pub has retained much of its original 19th century character.
The Metro bills itself as “Sydney’s newest old pub” — old because it was first established in 1834, new because it boasts a stylish rooftop terrace following a recent facelift. The four-storey venue contains a public bar, gaming room, restaurant and rooftop beer garden, linked by 87 infamous stairs that are a lot easier to navigate prior to indulging in a schooner — or seven.