Our neighbourhood is home to some of Sydney’s oldest and most iconic pubs.

We dig into the story behind some of east Sydney’s favourite watering holes.

The Woolly Bay Hotel
2 Bourke Street, Woolloomooloo

The first pub on this site on the corner of Bourke Street and Cowper Wharf Road was the Nell Gwynne Hotel (named for one of King Charles II’s mistresses), built in 1873. It was renamed the Macquarie Hotel, possibly around the turn of the century. The first Macquarie Hotel building was demolished in 1920 to make way for the current hotel, designed by architect Ernest Lindsay Thompson. The new building opened in April 1922 and was taken over by Tooth and Co (aka Resch’s) in 1929.

Handily located near the naval base at Garden Island, the ‘Rock n’ Roll’, as the pub was nicknamed, became a notorious sailors’ pub. During the 50s and 60s, a jazz band played classics like ‘Sweet Georgia Brown’ and ‘When the Saints Go Marching In’ in the main bar while the lounge hosted pool competitions and the kitchen served up sausage sangers. Legend has it that ‘the Rockers’ was the scene of some of Sydney’s wildest pub brawls. However, that all changed in 2012 when the pub (which had been renamed the Woolloomooloo Bay Hotel in the 90s) underwent a major renovation. It was transformed from an infamous ‘bloodhouse’ into a chic and trendy watering hole. Late last year, the pub underwent another metamorphosis, emerging as the Woolly Bay Hotel, complete with a new rooftop bar, restaurant and European-inspired fit-out overlooking the sparkling harbour.

The Tilbury Hotel
12-18 Nicholson Street, Woolloomooloo

The Tilbury began life as the Cowper Wharf Hotel in 1868. Woolloomooloo Bay was a growing commercial area thanks to the increasingly busy wharves, making it the perfect spot for an inn. The current building was erected in 1921-22, designed by well-known architects of the day, Copeman and Lemont. Like its neighbour, the Macquarie Hotel (now the Woolly Bay Hotel), the Cowper Wharf Hotel was owned by Tooth and Co. It took on the name Tilbury around 1927. The pub relied on the wharf and shipping trade for its clientele for many years until a new publican introduced a different vibe in the 70s. In 1972, Louis Ardilley took over the Tilbury’s lease, and it became known as ‘Louis at the Loo’, with crowds flocking to hear jazz bands play in the rear courtyard on Sunday afternoons.

Major renovations were undertaken at the Tilbury between 1999 and 2001, with another refurbishment following in 2015. These days the Tilbury is known for its modern contemporary cuisines, sunny outdoor spaces and heritage touches, like timber and brass finishes and original pub wall tiles.

The Courthouse Hotel
189 Oxford Street, Darlinghurst

Named for its proximity to the Darlinghurst Courthouse, this pub has been a major Taylor Square landmark for over a century. Established in 1890, by 1899, the Courthouse Hotel was described in the Sunday Times as ‘one of the best hotels in the city.’ The proprietor, Mr William Cordingley (‘a thoroughly practical man’), was reported to have just carried out extensive renovations. The hotel now boasted ‘all modern comforts’, including a large luncheon room and ‘nothing but the best of liquors’. It was said to be well patronised by the legal fraternity and ‘others doing business at the court during sessions.’ Plans were drawn up for further alterations in 1912 and again in 1914. It’s not known whether these works were carried out, but we do know that the entire pub was rebuilt in 1929. Its owners (Tooth and Co again) commissioned architects Prevost, Synnot and Ruwald, who worked on many hotels across New South Wales in the 1920s and 30s, to design the new building. Today, the Courthouse Hotel is heritage listed as a ‘fine representative example of an Inter-war Free Classical style hotel building’ and is renowned for its late closing time.

The Bourbon Hotel
22 Darlinghurst Road, Potts Point

The Bourbon Hotel began life in 1967 as the Bourbon and Beefsteak, which would go on to become one of Kings Cross’s – if not Australia’s – best-known pubs. It was one of the first venues in NSW to obtain a 24-hour liquor licence, and it was famous for its claim that its doors never closed. The man behind it was Bernie Houghton, an ex-CIA agent from Texas, who became such a respected figure in the local community that, after his death, a bust was erected in Fitzroy Gardens in his honour. The Bourbon and Beefsteak famously became a haven for US servicemen on leave from the Vietnam War, but over the years, it was also frequented by politicians, police, sports people, and hospitality workers, as well as everyday pubgoers.

After Houghton died in 2000, the Bourbon changed hands several times until it was bought by Iris Capital in 2015. The group is now undertaking a major refurbishment of the site, including the Bourbon and Empire Hotels. The end result promises retail shops, a medical centre, hotel accommodation, 52 apartments and revamped versions of the Bourbon and the Empire, both of which will hold 24 hours a day, 7 days a week licences. The design by TZG Architects and Panov Scott Architects promises to reinstate the Bourbon’s original arched openings and its famous three-storey bay window.

The New Hampton Hotel
9-15 Bayswater Road, Potts Point

The New Hampton’s forerunner, the Hampton Court Hotel, was built in 1915 on the site of the grand 1830s villa Goderich, once home to various titans of early Sydney Town. The Hampton Court Hotel began life as an apartment building, but in the 1930s, the flats were converted into hotel accommodations. The Hampton Court became one of Sydney’s leading hotels, hosting Elizabeth Taylor and her husband Mike Todd in 1957, as well as dancers from the Bolshoi Ballet. It made the papers in 1958 when workers threatened to strike if management introduced a six-day working week. A union representative complained that ‘no other residential hotels in Sydney had intentions of introducing a six-day working week’. The classic Australian film ‘They’re a Weird Mob’ was partially shot at the Hampton Court Hotel in 1966, and in the 1970s, the first-known recording of beloved Aussie rock band AC/DC was made there.

The Hampton Court Hotel closed its doors in 1998, and since then, it has been completely refurbished. It’s now a stylish apartment building once again, with the New Hampton pub nestled on the ground floor. The New Hampton prides itself on being Potts Point’s friendly local pub, with an extensive pub food menu and live local music every Friday night.

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Article by Jason Boon

In a real estate market that is the focus of Australian, and indeed worldwide attention, Jason Boon's results in the Sydney scene make him a highly significant figure within the industry. A long-term specialist in the Potts Point and inner eastern suburbs area, he is uniquely placed to leverage his skills and local knowledge as the area undergoes significant change and diversification. Jason ha…