One of Sydney’s most iconic thoroughfares, Oxford Street is synonymous with art, entertainment and queer pride.

Stretching from Hyde Park all the way to Bondi Junction via Darlinghurst, Paddington, and Woollahra, it is home to heritage Sydney landmarks like the Darlinghurst Courthouse, Victoria Barracks and Taylor Square.

Oxford Street’s origins

Oxford Street’s beginnings can be traced back to an Aboriginal walking path. In 1803, when convicts built a track from the fledgling Sydney Town to a signal station near South Head, it was constructed along an Aboriginal walking path known as the Maroo. Following an upgrade in 1811, the track became known as the South Head Road. Now the road was suitable for wheeled vehicles and the colony’s wealthy used it to access their villas in Darlinghurst, Potts Point, Darling Point, Point Piper and Paddington. Work on the new South Head Road, running closer to the harbour, began in 1831.

The Old South Head Road became an important high street after the construction of the Victoria Barracks in Paddington in the 1840s. This saw the road’s lower part rechristened Oxford Street in 1875 in homage to the London retail street of the same name. By 1932, the entire stretch of road from Hyde Park to Bondi Junction was known as Oxford Street.

A shopping mecca

By the end of the 19th century, Oxford Street was a flourishing commercial hub, home to food purveyors of all types, apothecaries, furniture shops, banks, photographic studios and tearooms. It was also an early bastion of multiculturalism, with many food shops run by Greek and Italian immigrants, Swiss and German-operated precision instrument workshops, and Spanish and Portuguese-run bodegas selling wine and produce. Meanwhile, many old mansions around Darlinghurst had been converted into boarding or lodging houses, and the local population was becoming increasingly working class.

In the early years of the 20th century, grand department stores, like Buckingham’s Department Store, sprang up on lower Oxford Street in Darlinghurst. Buckingham’s traded on Oxford Street for 60 years before it closed in 1968. Its building was destroyed by fire later the same year.

Widening the way

In 1909, Sydney Council decided to widen Oxford Street by 10 metres. As the main road east out of the city, and an increasingly popular shopping destination, it had become congested, noisy and polluted. Between 1910 and 1914, all the buildings on the northern side of the street between Hyde Park and Taylor Square were demolished to make way for the new, wider boulevard. New buildings were erected in the Federation style, most of which still stand today.

Further road widening plans ground to a halt thanks to the Depression and the Second World War, but in the following decades, plans were dreamt up to turn Oxford Street into a freeway running from the city to the eastern beaches. The spectre of these ‘will they, won’t they’ plans discouraged the upkeep of shops on Oxford Street and kept rents in the surrounding suburbs, like Darlinghurst, low. The neighbourhood had been popular with bohemians since the turn of the century, and now the cheap rents attracted migrant families and students too. Entertainment venues, like French’s Tavern and the Oxford Tavern, sprang up on Oxford Street to entertain the area’s young new residents. In the 1970s and 80s, these pubs gave early exposure to some of Australia’s best-known bands, including Midnight Oil, INXS and Cold Chisel.

The ‘Golden Mile’

It was during this era that Oxford Street became known as Sydney’s gay ‘Golden Mile’. Oxford Street’s proximity to the CBD heralded a regeneration for the street that lasted from the mid-70s to the mid-90s. Oxford Street’s first LGBTQ clubs, Capriccio’s and Ivy’s Birdcage, opened in 1969, and in 1978, the street was the setting for Sydney’s first-ever Mardi Gras. By the beginning of the 1980s, Oxford Street was home to gay bars, clubs, saunas and cafes, and the street and the surrounding neighbourhoods of Darlinghurst and Paddington became known as safe and welcoming areas.

Looking to the future

Since the turn of the millennium, Oxford Street’s fortunes have been mixed. Many businesses and venues have closed, while the nightclubs and bars that remained suffered through lockout laws and lockdowns. Now, Sydney’s main business group, Business Sydney, is proposing that responsibility for the street be handed over entirely to the City of Sydney. At the moment, the northern side of Oxford Street in Paddington is the responsibility of Woollahra Council, while the southern side lies with the City of Sydney and the road itself is owned by the state government. Business Sydney suggests that the fragmented management of Oxford Street is muddying its future and “transferring ownership and responsibility to a single council is an important first step in making Oxford Street a go-to place in its own right.”

There are also high hopes that WorldPride will draw visitors back to Oxford Street this year. Sydney is hosting the global LGBTQIA+ festival over two weeks in February and March to coincide with Mardi Gras. It’s expected the event will attract 500,000 people to the more than 200 events that make up its program. Here’s hoping it gives Oxford Street, still to this day one of Sydney’s most iconic addresses, a much-needed shot in the arm.

If you’re thinking about buying, selling or investing on Oxford Street or the surrounding Darlinghurst neighbourhood, get in touch today.

Photo credit: Wikipedia

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…