To the east of the city centre the adjacent districts of Kings Cross and Potts Point comprise one of the city’s major entertainment districts and a popular spot for tourists (particularly backpackers). To the north you can descend a series of steps to Woolloomooloo with its busy naval dockyards and stylish Finger Wharf. South of Kings Cross, Darlinghurst and Paddington were once rather scruffy working-class suburbs, but were gradually taken over and revamped by the young, arty and upwardly mobile.
Oxford Street runs from the city southeast through Taylor Square, the heart of gay Sydney and on through the designer shopping and art gallery areas of Darlinghurst and Paddington to old-money Woolahra and the open grasslands of Centennial Park.
Oxford Street marks the northern boundary of rapidly gentrifying Surry Hills. While cutting-edge galleries and bars are still filling the area’s backstreets, others are looking south to go-ahead Waterloo and even edgier Redfern.Read More
Paddington, a slum at the turn of the twentieth century, became a popular hangout for hipsters during the late 1960s and 1970s. Yuppies took over in the 1980s and turned Paddington into the smart and fashionable suburb it is today: the Victorian-era terraced houses, with their iron-lace verandas reminiscent of New Orleans, have been beautifully restored. Many of the terraces were originally built in the 1840s to house the artisans who worked on the graceful, sandstone Victoria Barracks on the southern side of Oxford Street, its walls stretching seven blocks, from Greens Road to just before the Paddington Town Hall on Oatley Road. The barracks are still used by the army, though you can visit a small museum of uniforms, medals and firearms. Free tours include an army band recital.
Shadforth Street, opposite the entrance gates, has many examples of the original artisans’ homes. Follow this street north then turn right onto Glenmore Road to reach Five Ways, the focus of an area of pleasant, winding, tree-lined streets that make a great place for a stroll, and offer a chance to wander into speciality stores, cafés and numerous small art galleries.
The area’s swankiest clothes shopping is around the junction of Glenmore Road and Oxford Street, and there are more classy shops further east on Elizabeth Street, which runs off Oxford Street almost 1km further southeast. Always bustling, the area comes alive on Saturday when everyone descends on Paddington Markets in the church grounds at no. 395. The markets just keep getting bigger, selling everything from handmade jewellery to local artwork, cheap but fresh flowers and vintage clothes.
South of Darlinghurst’s Oxford Street and due east of Central Station, Surry Hills was traditionally the centre of the rag trade. Rows of tiny terraces once housed its poor, working-class population, many of them of Irish origin. Considered a slum by the rest of Sydney, the dire and overcrowded conditions were given fictional life in Ruth Park’s The Harp in the South trilogy, set in the Surry Hills of the 1940s. The area became something of a cultural melting pot with European postwar immigration, and doubled as a grungy, student heartland in the 1980s.
By the mid-1990s, the slickly fashionable scene of neighbouring Darlinghurst and Paddington had finally taken over Surry Hills’ twin focal points of Crown Street, filled with cafés, swanky restaurants, funky clothes shops and designer galleries, and parallel Bourke Street, where a couple of Sydney’s best cafés lurk among the trees. As rents have gone up, only Cleveland Street, running west to Redfern and east towards Moore Park and the Sydney Cricket Ground, traffic-snarled and lined with cheap Indian, Lebanese and Turkish restaurants, retains its ethnically varied population.