Neighbourly love
Heading to Sydney any time soon? Make sure you make a beeline for Paddington
The now sought-after Paddington neighbourhood was once considered by most Sydneysiders as a slum. Impoverished tenants crowded into the higglegy-piggledy Victorian terraces. As is the way in so many urban areas, think New York City’s Meatpacking District, the affordability of these areas attracted creatives and outliers. By the 1990s ‘Paddo’, as it’s fondly referred to, was home to iconic clubs including Patches, The Abury, and the Sleaze Ball at Paddington Hotel where pop queen Kylie performed a surprise gig in 1994. Wheels and Dolly Baby and Route 66 rockabilly-style fashion stores popped up along with the Ariel Bookstore and a slew of pubs and late-night cafes including Jackies with its red booths and thick shakes, and Home Diner, a renowned post clubbing spot. As Bart Celestino, Editor of Sydney-based contemporary art, photography and fashion magazine, LoveWant said, “Back then you were just as likely to run into Bono as you were to Ru Paul. We used to say you will meet everyone you know on Oxford Street at 3am on a Saturday morning!”
Paddo is where creativity hums quietly on the side streets
These days, those once humble workers houses are heritage-listed homes, laced with intricate ironwork balconies, woven with lilac wisteria. Walk up to William Street for a stunning collection of terraces-turned-shops and cafes, and weave your way through the backstreets to view some of the most covetable houses. Breakfast here is legendary, especially where Paddington bumps up against Darlington. Local secret Tenacious Bakehouse delivers the best French pastry with a Korean twist. Whilst the Organic Bread Bar on South Dowling Street is the place to head for its famed croissant-pretzel hybrid and crusty sourdough loaves. Just opposite is Sydney’s most famous sandwich shop, South Dowling Sandwiches, (don’t skip the caramalised carrots). As evening draws in and the streetlights blink on, order a natural wine and an Italian dish at Paski Vineria Popolare. The ‘P’ in Paddington probably stands for pub. Stand out spots include The London, The Paddo Inn, The Village Inn and The Unicorn.
While Paddington is known for its sandstone pubs and perfectly peeled lattes, it’s also where creativity hums quietly in the backstreets—best discovered on foot, flat white in hand. Recently opened Qtopia Sydney occupies the former Darlinghurst Police Station—a site historically associated with the oppression of Sydney’s LGBTQIA+ community. The new transformation of this space into a centre for education and celebration symbolizes a reclamation and acknowledgment of past injustices. Over the road The National Art School, operated within the old goal and hosts open days and nights throughout the year, displaying student works alongside food and bar pop-ups and live music.
The Sherman Contemporary Art Foundation (SCAF) is tucked behind a discreet brick façade on Goodhope Street. Founded by arts patron Dr. Gene Sherman, this thoughtful gallery space punches well above its weight, hosting bold, often provocative contemporary art installations from around the world. The leafy courtyard often features site-specific sculpture, and entry is free.
A short walk away, Paddington Reservoir Gardens offers more than just a quiet moment. The beautifully restored 19th-century reservoir blends industrial ruins with manicured gardens and floating walkways, creating a space that feels part Roman ruin, part design installation. It’s often described as Paddington’s answer to New York’s High Line—minus the crowds.
If you fancy a brilliant secondhand bookstore browse, head to Berkelouw Books, Australia’s oldest and largest independent bookseller, or Ampersand is three-stories of over 30,000 secondhand books across various genres. And if clothes are more your thing, the heart of Australian fashion designers beats on the corner of Glenmore and Oxford. This small intersection houses Sydney’s biggest international exports including Zimmermann, Scanlan Theodore, Bassike, Aje, Camilla and Marc, Ginger & Smart, Venroy and more. Compliment this with accessories a little further up Oxford street at Sarah and Sebastian (where you can solder to order) and famed Dinosaur Designs, proving everything looks better in resin.
