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The perfect place to wander on foot, Chippendale offers a wonderfully eclectic mix of style, creativity, and innovation. Some of the city’s most loved drinking and dining venues have long called the suburb home but the emergence of newly imagined entertainment precincts has really pushed the locale forward into a vibrant new era.

One of these precincts is the 5-star green-rated Central Park complex, built around the old Kent Street Brewery and home to an eclectic array of restaurants, galleries and shops. The aesthetic of this place is impeccable with green walls seemingly making up most of the external structure of Central Park Mall and a super-sized interactive wall permanently installed as digital art. The creative and forward-thinking design flows through to the retailers and eateries inside and you’ll find offshoots of some of Sydney’s most popular restaurants here. 

Having transformed from a once-grungy industrial neighbourhood into a funky playground of cool cafés, hipster pubs, hawker-style eateries, and artisan food specialists, Chippendale is one of Sydney’s culinary hubs. It is home to some of Sydney’s best loved fine dining, with Ester, Automata and LP’s Quality Meats being the pick of the bunch. All three have perfected the balance between accessibility and sophistication, meaning that while you’re indulging in first-rate food, the ambience is warm, friendly and relaxed. White tablecloths be gone! 

Automata offers a constantly changing five-course degustation, while Ester and LP’s offer a-la-carte and set menus. Just remember to arrive hungry or you’ll be faced with tough decisions around which dishes are worthy of your stomach space. For more casual fare, there’s a great choice of eateries in the hawker-style Spice Alley, where you can BYO wine and enjoy an inexpensive meal with Asian flavours, from roti, rendang and rice paper rolls to dumplings, satays and stir-fries. It’s best enjoyed with a group of friends, sharing plates from different stalls.

If you’re after a good watering hole to end the night, Chippendale has a plethora of options. As a nod to the suburb’s history, a number of old pubs still exist. The Lord Gladstone is one such establishment and is a great option for a relaxed drink. For a completely different ambience, Zigi’s Wine Bar is the kind of place where you pop in for a drink and end up staying all night. The extensive wine and cheese selections reflect Zigi’s Israeli heritage, and the murals on the walls and upstairs art gallery provide food for thought. 

Other Chippendale watering holes to put on your list include The Rose Hotel and The Duck Inn (both with attractive beer gardens), Sneaky Possum (for casual bites and craft beers), and Handpicked Cellar Door. For sweet satisfaction, head to KOI Dessert Bar in Kensington Street, where ex-MasterChef contestant Reynold Poernomo casts a spell over diners with impossibly beautiful cakes and desserts.

One of Chippendale’s biggest surprises is the White Rabbit Gallery, offering four floors of contemporary Chinese art. It’s free to enter and visitors can while away hours inspecting the owner’s private collection as well as displays in the rotating exhibition space. The pieces are unique, thought provoking and always a talking point. Before you leave, stop in at the teahouse on the ground floor where a whole new world of tea awaits, along with delicious handmade dumplings. There is also a mini cinema, library and gift shop.

Delve deep into the fabric of Chippendale on a 90-minute walking tour with the Australian Architecture Association. Its knowledgeable volunteer tour guides reveal aspects of Sydney history that might surprise you, and they’ll tell you all about the incredible amount of planning and design that has gone into the Central Park complex.

When you tire of wandering, escape to the inner sanctum of the Adina Apartment Hotel Sydney Chippendale, in a quiet residential location just metres from the action. Its spacious studio rooms and apartments are set around a leafy courtyard with an outdoor plunge pool. And with a newly-launched program of events - Yoga in the Courtyard anyone? - it's the perfect place to while away those precious holiday hours.

** Peace of mind when you stay with us: Introducing Clean Touch. Note some activities listed may be subject to Covid restrictions. **