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Many of Paddington’s lovely terrace houses, with their narrow frontages, iron-work verandahs and pocket-handkerchief gardens, were erected following the construction of the Victoria Barracks in the 1840s. The area went into decline during 1931′s Great Depression, but an influx of migrants revitalized the area after WWII. Many of those migrants moved out following the suburb’s gentrification in the 1960s and ’70s. Some of the most interesting examples of the Victorian terrace style are found in Glenmore and Jersey Roads, and Cascade, Liverpool, Windsor and Paddington Streets.

Victorian terrace houses in Paddington

This just might be Sydney’s best loved weekend market. It’s held every Saturday in the pleasant, shaded grounds of Paddington Village’s St. John’s Uniting Church. Ever since 1973, this al fresco bazaar has been a great place to shop for jewellery, crafts, fashion, pottery, soaps, second-hand clothing and the like. It’s always had a New Age bent, so you’re also likely to find someone who can massage those travel-weary shoulders, read your tarot cards or fine-tune your chakras.

This Classical Revival Town Hall on Oxford Street was designed by J Kemp, a local architect who won an international competition to design a civic centre that matched the suburb’s increasing status. The main building was completed in 1891, and the clock tower that now dominates was added several years later. The hall underwent extensive restoration work in the 1990s and is no longer used by the council. But it does house the suburb’s library, offices, cinemas and a radio station. It is also a regular venue for private functions and corporate events.

Robert Cooper (1776–1857) was one of Sydney’s more successful emancipists and a self-confessed smuggler. Originally sent down for receiving stolen goods, he made a small fortune as Sydney’s first distiller, specializing in gin flavoured with juniper berries: hence the name of this residence. Diagonally opposite the Town Hall, it was built in 1824 to house his 28 children from three marriages. The house was threatened with demolition for several years, but finally spared in the 1980s and restored by the National Trust. It is closed to the public, but you can view it from Oxford Street.

Occupying 12 ha (30 acres), these barracks were built between 1841 and 1848. They are immediately recognizable from Oxford Street by their high sandstone walls; many regard this complex of late Georgian buildings as one of the finest military barracks in the world. The architect was Major George Barney, who also designed Fort Denison. Until 1870 the barracks were home to British troops; today they are an Australian Army facility. The Army Museum is housed in the former military prison and contains several interesting exhibits tracing the military heritage of New South Wales.

Oxford Street is Sydney’s most fashion-conscious shopping strip. Although it runs all the way from Hyde Park to Bondi Junction, the prime shopping drag is on the north side of the road between Barcom Avenue and Queen Street, which runs down to Woollahra. Surry Hills’ Crown Street is less conspicuous and polished than its northern rival, but it’s gaining a reputation as a good spot to source homewares, designer and retro furniture and fashion items. It has some great cafés, ethnic restaurants and grocers, pubs and factory outlets, and its grunginess is the perfect antidote to Oxford Street’s fashionista frenzy.

Stationed at Victoria Barracks in 1851, the British Army were told to take their bats and balls and entertain themselves on the empty land south of the barracks. Ever since, this site has been the spiritual home for millions of cricket-mad Sydneysiders. In January 1928, fans saw Sir Donald Bradman’s first-class cricket debut and, in January 2004, Australian test captain Steve Waugh took his final bow here. It has also hosted concerts by the Rolling Stones, Madonna and others, as well as the occasional Australian Rules football match.

Sydney Cricket Ground

Designed by Phillip Cox, this stadium (see Tankstream & Aussie Stadium) was completed in 1988 to coincide with Australia’s Bicentenary. Although the ground was ostensibly designed for Sydney’s preferred football code, Rugby League, it has occasionally permitted upstarts from the southern code, Australian Rules, to take to the field. During the 2000 Sydney Olympics it even allowed its turf to be trampled by soccer players. Aussie Stadium has also held several concert performances, which have included shows by U2, Robbie Williams and Barbara Streisand.

Since opening in 1998 these studios have created Moulin Rouge , The Matrix series, Mission Impossible II and Star Wars: Episode II . The massive entertainment complex houses 15 restaurants, bars and cafés serving everything from Asian to Mediterranean fare. For the kids there’s mini golf, cinemas, bungy trampolines, seasonal ice skating, an interactive TV studio, an indoor playgound, bowling and electronic games. There are also four live performance venues and numerous shopping options. The Farmers Market offers gourmet delights from the country, and the Weekend Market has gifts, clothes, movie memorabilia and crafts.

Tucked down a Surry Hills backstreet, the former studio of artist Brett Whiteley is now a public museum and art gallery. Whiteley painted some of Sydney’s most iconic works. He loved the harbour and the nude, and both feature in his paintings. In 1985 he converted this former factory into a studio but, just seven years later, he was found dead from a heroin overdose in a motel room in the south coast township of Thirroul. The gallery has regular exhibitions and displays the artist’s studio much as it was before he died.