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Blow your mind at White Rabbit and other art galleries

Start your art exploration at the remarkable (and free) four-storey White Rabbit Gallery, radically transformed from an old knitting factory and now housing the world's largest and most significant collection of contemporary Chinese art outside China. Enjoy a free guided tour to understand the edgy political pop art, enormous sculptures and other eccentric creations on display. The cafe serves fabulous dumplings and a wide range of Chinese and Taiwanese teas including oolong, white teas, chrysanthemum teas and cooling lychee or green iced tea. Visit Galerie Pom Pom for cutting-edge installations from the hottest Sydney and Melbourne-based artists, artist-run Wellington St Projects for its provocative raw works, and Tiny Tailor for artworks and singular design pieces. 

Explore neighbourhood street art

While you're in the neighbourhood, check out its impressive street art. The upstairs Goodspace gallery at the Lord Gladstone Hotel exhibits the work of street artists. If you would rather explore with a local guide, take the Chippendale-Redfern Tour with Culture Scouts, which combines visits to art galleries and shopping boutiques with the insider story on how this area evolved. For more information on the Chippendale arts scene check out the Chippendale Creative Precinct.

Admire the cutting-edge architecture

Since Sydney’s earliest days, Chippendale had been a slum surrounding an enormous brewery. When the brewery closed in 2005, the visionary Dr Stanley Quek decided to transform its heritage buildings into one of Australia’s most exciting urban renewal precincts. Now called Central Park, it is a mixed-use urban village blending apartments, offices, shops, restaurants and a public park. Go for a stroll to admire its sustainable skyscraper covered by the world's tallest vertical garden. Wander around outdoor sculptures, including Turpin and Crawford's minimalist Halo. Across the road at the University of Technology Sydney, is the first Australian building designed by Frank Gehry, nicknamed "the squashed brown paper bag building". As you wander, look out for heritage-listed Strickland House, Sydney’s first public housing project, as well as White Rabbit Gallery owner Judith Neilson’s house Indigo Slam, designed as a piece of sculpture to be lived in.

Feast affordably

Feast on Asian street food at contemporary outdoor foodie destination Spice Alley, where permanent stalls are lined up across the facade of Kensington Street's heritage terrace houses and a small lantern-lit courtyard buzzes with happy diners. The stalls are run by veterans of some of Sydney's most popular South-East Asian restaurants, specialising in everything from Malaysian cuisine to Hong Kong fast food. This vibrant collection of hawker-style eateries is truly one of Sydney's hidden gems.

Or splurge on something more upmarket

For cutting-edge dining, go to Ester, which offers a sublime and reasonably priced experience in a pared-back space with an open kitchen. LP's Quality Meats is the place to go for smoked and cured meats as well as negroni cocktails and classy wines. And for all your bread, pastry and coffee needs, head to Brickfields, which is primarily a bakery and takeaway coffee bar. Must-haves include a ciabatta roll filled with chorizo and spiced red cabbage, and syrup-soaked Persian love cakes. Buzzing Café Giulia, a long narrow space in a renovated 100-year-old butcher shop, offers inspired lunchtime bagels, rolls and burgers plus good coffee, juices, beer and wine. Ippudo, downstairs in the Central Park complex, is the first Australian branch of the famed Japanese ramen stores and does some of the best ramen in Sydney.

Rest your head and dine in-house 

Stay at the edgy, boutique Old Clare Hotel, which has been cleverly created from the historic bricks, concrete and timber of an old pub and the adjacent Carlton United Brewery Administration Building (they’re joined by a glass and steel atrium). The rooms have a pared-back, post-Industrial feel, with much of the original brickwork exposed. Soak up some of Sydney’s famous sunshine at the rooftop lap pool and bar. Enjoy witty dishes at the casual, high-ceiling, stone-pillared, all-day brasserie Kensington Street Social. Or try an inspired seasonal degustation menu (which changes weekly) from Clayton Wells (formerly of Momofuku Seiobo) at sleek, monochromatic Automata

Drink creatively

There are pubs for all persuasions in Chippendale. The Rose Hotel is popular with the university crowd as well as locals watching the rugby league. The beer garden out back is perennially popular. The Duck Inn Pub & Kitchen has been reimagined with an airy, almost beachy decor, complete with board games, a packed bookshelf and a sunny beer garden with umbrellas and picnic tables. Enjoy a great selection of craft beers, interesting wines and a seasonal menu of updated pub classics. Zigi's Art Wine Cheese Bar has an interesting concept while it waits for their liquor licence: it is operating as a bring your own (BYO) wine bar while it supplies the cheese. The selection of Australian and international soft, hard, white mould, and washed rind cow, sheep and goat's cheese is sensational. Freda's is a neighbourhood bar with an artsy vibe that every so often does a zany light installation with sound and video.

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