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Paddington terraces1/2
Photograph: Supplied/Woollhara Muncipal Council
Paddington five ways2/2
Photograph: Supplied/Woollhara Muncipal Council

A local's guide to Paddington

Wander the heritage terraced streets of Sydney's fashion village and discover great coffee, fine dining, and quirky enclaves

By Alannah Maher and Time Out editors
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Paddington, or “Paddo” as it is lovingly known, is nowadays one of Sydney’s most desirable suburbs. A heritage village dotted with boutique stores and hemmed by rows of Victorian-era houses, the streets combine old-world influences with modern flair. You’ll find some of the city’s most well-dressed (and well-heeled) folk here, walking the pavements with their equally fashionable designer dogs.

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EAT DRINK COFFEE THINGS TO DO SHOPPING

What’s Paddington known for?

At the heart of Paddington is ‘the Intersection’, a high street retail precinct with a village feel where Oxford Street and Glenmore Road meet. The area first began to emerge as a destination for local and international fashion in the 1960s – before this, it was largely regarded as a working-class suburb. 

By the ’90s, the Paddington end of Oxford Street was established as Sydney's fashion epicentre. The area’s terrace-converted shops have long been a breeding ground for up-and-coming design talent, able to retail on street level and use the upstairs as spaces for manufacturing, offices, or living. 

The land now known as Paddington traditionally belongs to the Dharug (or Eora) language group, and is associated with the stories of the Cadigal people. The ridge on which Oxford Street was built was also an efficient walking track used by the area’s original inhabitants. 

Why do the locals love it?

Husband and wife Joe and Rose Cipri have lived in Paddington for 20 odd years, and Joe and his brothers, Carmelo and Anthony, opened their first restaurant in Paddington ten years ago after three decades in the restaurant business. So what drew them to Sydney’s east? “For me, it's the community,” says Joe. “I feel like it's a friendly, lively, well-travelled community.” Rose adds: “They appreciate good quality food and good quality wine, and they love having a chat about food, travel and culture. That’s what we love doing as well.” 

Tucked away around a corner and up a set of stairs, Cipri (10 Elizabeth St) is a restaurant with a genuine family feel. Any night you can walk in and one or all three of the brothers will be there, the walls are covered with a selection of family photos from over the years, and on the menu are Italian dishes inspired by their Calabrian parents. After having run three other restaurants around Sydney, Joe says this is the first place where they felt confident giving it the family name: “It's the one restaurant where I really feel like we’ve immersed ourselves in the community. Everyone who walks past waves and says 'G’day'.” 

The family opened their second restaurant, Barbetta (2 Elizabeth St), right next door as a daytime café counterpart after customers expressed their desire to see the Cipri’s for their morning coffee. Here you can find an Italian take on the Aussie café brekkie, fresh pasta for lunch, and a wall of house-made and imported European groceries and ready-made meals. Barbetta is also where the family runs pasta making classes, cooking workshops, and Italian language classes. Joe and Rose say people from all over Sydney, who’ve had their 2020 European travel plans cancelled for the foreseeable future, have been coming to them to get a taste of bella Italia in the meantime. 

How do I get to Paddington?

Busses running from Central serve Paddington well; the 440 from Eddy Avenue will get you to Paddington Town Hall in 10 minutes, and the 389 line between Bondi Junction and Pyrmont has six stops in Paddington. From Central Station, you can take the T4 line towards Bondi Junction and get off the train at Edgecliff Station (5 minutes), from there the Paddington end of Oxford Street is about a 20 minute walk. 

What’s nearby?

Sandwiched in the middle of Sydney’s Eastern Suburbs, Paddington is just three kilometres east of the Sydney CBD. Follow Oxford Street to the west and you’ll hit Darlinghurst, with the city’s epicenter of gay bars and nightlife; follow Oxford Street in the opposite direction past Centennial Park and Woollhara and you’ll reach Bondi with its refined take on relaxed beachside living. To the south is Moore Park.

Map of Paddington

If you only do one thing

You can easily while away a day in Paddington, admiring the architecture of the terraced streets and popping into shops and cafés. But if you can only pick one day for it, go there on a Saturday and check out the Paddington Markets (395 Oxford St), which takes over the grounds of Paddington Uniting Church and the neighbouring public school with more than 100 stalls selling Australian-made fashion, handmade crockery and metal costume jewellery. The markets re-launch on September 26 after lockdowns with a new growers market for all your fresh produce desires. 

Upstairs in Opus store, Paddington
Upstairs in Opus store, Paddington
Photograph: Supplied/Cipri

Eat

In addition to the fashion and shopping, deluxe restaurant dining is another of Paddington’s major drawcards. Fred’s (380 Oxford St) is an inclusive fine diner with a rustic heart that has taken the open kitchen concept to its apex, removing the walls entirely so that the dining room and kitchen are one and the same.

Saint Peter (362 Oxford St) is devoted wholly and exclusively to the fruits of the sea. Under the direction of chef Josh Niland, who has committed his career to seafood, brunch becomes a pescatarian dream with smoked eel served on pikelets and uni on crumpets, and at dinner time, a tangle of octopus legs are punked up with a feisty XO and silky squid ink. A couple of doors up, Fish Butchery (388 Oxford St) is the expansion of Niland’s empire, serving sustainable prime cuts from the ocean and the best takeaway fish and chips in town.

The Cipri family also has you taken care of for soul-warming Italian food. Of an evening, Cipri is a welcoming place to sit down to a plate housemade pasta, Rose and Joe’s top pick is the ‘Pappardelle con ragu d’anatra e funghi’ with thyme pappardelle, slow braised duck, and swiss brown mushroom ragu. At Barbetta, they say you can’t go past the ‘Best ever lasagne’ for lunch. For fresh South East Asian food, Joe and Rose also love to get down to Chubby Cheeks (437 Oxford Street) for modern Thai dishes designed to share. 

Across the road from the UNSW Art & Design campus, Indian Home Diner (86 Oxford St) is a popular port of call for those on a student budget to pick up a late-night Indian kebab.

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People sitting inside of restaurant at 10 William Street
People sitting inside of restaurant at 10 William Street
Photograph: Anna Kucera

Drink

In more usual times, Paddington is begging to be explored via bar and/or pub crawl. You have a selection of wine bars and fancier drinking dens that pair harmoniously with the neighbourhood’s finer dining establishments, as well as a collection of characterful pubs. With a reputation that precedes it, 10 William Street (10 William St) is an Italian wine bar that holds its own. Order a glass of natural wine, something like a Timo Mayer Yarra Valley Cabernet, and just try to resist chasing it down with a steamy bowl of pasta or a tiramisu. The Wine Library (18 Oxford St) is a learned seat of good vines and snacks, and arguably the best place along Oxford Street for a deep dive with wine-loving bartenders. Tequila Mockingbird (6 Heeley St) a 100-seat, two-storey terrace where the retractable rooftop lets in the midday sun (perfect for sipping fruity house cocktails under), and downstairs is an eight-seat bar where you can work your way through the 32 tequilas and 10 mezcals on the menu, plus rums from Guatemala and around Central America.

When it comes to pubs, The Intersection’s Village Inn (9-11 Glenmore Rd) is the area’s oldest, and like many of Paddo’s old faithfuls has had a modern makeover that still preserves the heritage. Upstairs at the Village Inn you’ll also find the Print Room, a hidden cocktail bar with pretty drinks and old-world glamour. For a more chilled out pub vibe, the Light Brigade (Cnr Oxford St and Jersey Rd) is where it's at, with a rooftop boasting some of the best city views you’ll find. The Paddo Inn (338 Oxford St) is another old pub with a modern makeover, serving up a no-fuss bar and grill menu with all the greatest hits. If darts is the name of the game, The Lord Dudley (236 Jersey Rd) has one of the best dartboards in the city, and plenty of cute plants to boot. The Unicorn Hotel (106 Oxford St) is a true-blue, dinky-di Aussie watering hole from the Mary’s Burgers gang.

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Making coffee at Ampersand
Making coffee at Ampersand
Photograph: Cassandra Hannagan

Coffee

You won’t get far in Paddington without running into a café. From quick caffeine hits to coffee houses where you can linger, this ‘burb has you covered. Head down a street art-covered alleyway to find Not Just Coffee (264 Oxford St), serving Single O brews along with soulful bites like sandwiches and peanut butter and jelly muffins. If you have some time to sip away, we highly recommend finding a quiet corner of Ampersand Bookstore Café (78 Oxford St) to tuck away with a first edition and a cuppa brewed on Little Marionette beans (brunch is also top shelf here), in this multi-level enclave you can peruse the bookshelves, soak up that musky, comforting second-hand book store smell, and even bring some titles to part with if you’re so inclined.

A handful of small delicatessens and cafés call back to Paddington’s European immigrant roots. Omeio (31 McDonald St) is a prime example, while many of the cheeses and cured meats on offer are sourced from Europe, the coffee beans are Australian-grown, from the Big Marquee in Queensland. Paddington Alimentari (2 Hopetoun St) is a neighbourhood café that bridges the divide where the retail stretch of William Street meets the residential, serving Allpress coffee under hanging salamis and prosciutto. 

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Person walking through park at Paddington Reservoir Gardens
Person walking through park at Paddington Reservoir Gardens
Photograph: Cassandra Hannagan

Things to do

Culture is more than fashion and lattes in Paddington. Contemporary art is a huge part of the local vibe. UNSW Galleries (cnr Oxford St and Greens Rd) on the UNSW Art & Design campus hosts major exhibitions from Australia and overseas as well as student showcases. Until November 2020, the gallery is exhibiting the provocative and heartfelt collection Friendship As a Way of Life, which explores queer kinship and has transformed the foyer into a colourful “dyke bar”. The small but mighty Roslyn Oxley9 Gallery (8 Soudan Ln) also features top-flight local and international artists, currently showing The Gardener’s Eye, the latest glimpse into the weird and wonderful world of artist Patricia Piccinini. Saint Cloche (37 MacDonald St) is a light-filled space that elevates emerging artists and showcases mid-career movers and shakers. If you’re looking to flesh out your own art collection, Paddington is dotted with a smattering of small, specialised commercial galleries. Blender Gallery (16 Elizabeth St) has fine art music photography and limited edition rock n’ roll prints; Cooee Art Gallery (326 Oxford St) hand-picks Aboriginal art; Blinq Art (84 Oxford St) does prints by Aussie artists; Juniper Hall (250 Oxford St) is the permanent home of the Moran Arts Foundation Collection and the Moran Prizes; and Lyons Gallery (248 Glenmore Rd) has you covered for celebrity and fine art photography.

If you’re looking for somewhere peaceful to pass some time without spending any money, Paddington Reservoir Gardens (251-255 Oxford St) is the area’s hidden gem. This sunken Romanesque garden has in previous incarnations served as an early 19th-century water reservoir, a garage, a petrol station, and a hub for budding graffiti artists. This otherworldly underground oasis is now a cultural precinct hosting markets, art and film festivals – however, it can be best enjoyed as a shady green retreat on a quiet day. The sprawling Centennial Parklands (between Oxford St, York, Darley, Alison and Lang Rds) is also one of Sydney’s finest places to take a picnic or sit under the shade of a tree with a book.

Want a flick? The Palace Verona (17 Oxford St) cinema shows the latest arthouse and foreign flicks and the historic, beautiful Chauvel (cnr Oxford St and Oatley Rd) in the old Town Hall will transport you back in time.

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Upstairs in Opus store, Paddington
Upstairs in Opus store, Paddington
Photograph: Alannah Maher

Shopping

We’ve already touched on Paddington’s focal point for shopping and fashion, The Intersection. The precinct was given a makeover during the late ’90s and early ’00s to concrete its place as an Australian fashion precinct, after a mass exodus of international retailers to the malls that bookend Oxford Street. Now you’ll find boutiques from some of Aussie fashion’s major players like Sass & Bide, Alice McCall and Camilla rubbing elbows with young up-starts. Some of the best curated fashion stores in the area include Parlour X (261 Oxford St), which resides in the architecturally beautiful, historic St Johns Church building; Incu (258 Oxford St); and Come as You Are (443 Oxford St).

While the high fashion may be the drawcard for many of Paddo’s visitors, that’s not all you’ll find on a shopping expedition. Heading east from The Intersection, the fashion boutiques mix in with stores sporting stylish homewares and some more common high-street brands like Country Road and Birkenstock can be sighted. The op shops are also great places to rummage for bargains and designer finds surrendered from the well-heeled wardrobes of the locals. Paddington has the only Vinnies (292 Oxford St) we know of with three storeys and an aesthetically pleasing annex.

Among the very Paddo-feeling shops is Bag-All (400 Oxford St), a store flagshipped in New York that specialises in fashionable bags (you guessed it) and cases in reusable fabric to organize all aspects of your life, from customizable totes to specific travel cases. Opus (354 Oxford St) has been a fixture of Paddington for more than 50 years. A hub of gifting and homewares, you’ll find novelty finds downstairs and more refined finds from local designers and makers upstairs (Inner Westies may recognise the vibe from their smaller Newtown outpost, Octopus). Another more unconventional find is Aquadisiac (448 Oxford St), the dancing jellyfish in the front window draw customers into this aquarium store, which also maintains many of the fish ponds of Eastern Suburbs yards. Heading west towards Darlinghurst, you’ll find treasures like Berkleouw Books (19 Oxford St), a three-level emporium of readables and curios with a café and wine bar within (stay tuned for this to return to serving, pending restrictions). 

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William Street Festival Paddington jeans
William Street Festival Paddington jeans
Photograph: Kelly Hulme

Mark your calendar

Paddington has many charming side streets latching off the main drag of Oxford Street, but William Street is arguably the king of them. This boutique shopping lane hosts an annual event, William Street Festival, blocking off traffic and filling up the lane with fashion markets, food stalls and music from just before lunch and into the evening. Many of the street’s much-loved retailers usually offer special discounts on the day too. In 2020 the festival will not be going ahead due restrictions in place regarding you-know-what, but the locals will be waiting with bated breath for the next edition.

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