The five coolest streets in Sydney – as voted for by Time Out’s readers

While King Street claims a lot of the glory, the other main artery of Newtown – joining up with Enmore (of course) and Marrickville – is a haven of excellent restaurants, bars and pubs and boutiques with a taste of the local ‘weird is welcome’ edge. If you could eat your way through every single place to grab a bite on this strip, we’d be impressed. The action centres around the historic Enmore Theatre (118-132 Enmore Rd). The Art Deco landmark is a legendary culture hub with creds in live music and comedy gigs. While some of the portals to the street’s old character have succumbed to shiny new fit-outs (RIP, Sly Fox Hotel) there are still remnants of Enmore Road’s rough-n-ready, laid-back charm and inclusive spirit. 

EAT Behind the beautiful pink and purple, retro curved glass façade of the Marie-Louise Salon you’ll find Stanbuli (135 Enmore Rd), a good-time restaurant from the Porteño team serving proper Turkish food. Order up some midya dolma to sate your rumbling tum while you have a pre-dinner drink. They’re little mussels stuffed with peppery, allspice-scented rice and they’re stupidly delicious. Get at least two apiece.

DRINK Start your drink crawl (or finish your night) at Jacoby’s (154 Enmore Rd), a party-starting Tiki bar decked out in glowing fishing floats, dried pufferfish, and flocked banana palm wallpaper. They’re also sporting some of the city’s most ridiculous cocktails, and a whole lot of Twin Peaks references for die-hard fans.

BUY Get your kicks, and a hit of Wild Western Americana, at Route 66 (2/82-84 Enmore Road). Many a cowboy boot-clad scallywag has entered this boutique on the hunt for a perfectly aged Creedence tee or a frilly rockabilly dress. 

Discover the best of the neighborhood: a local’s guide to Newtown

In 2020, Time Out named Marrickville as the coolest neighbourhood in Sydney (and the tenth coolest in the world), so it’s little wonder that the main street through the heart of this suburb should make this list. Marrickville is a cultural melting pot, and that is on full display along its namesake road. Heavily influenced by waves of Greek and Vietnamese residents, with a healthy dose of creative colour on top from the Inner West’s rainbow and arts communities, it’s a street where you’ll meet a dynamic mix of people and businesses – a true snapshot of Sydney’s multicultural soul. 

EAT It smells like heaven in the Lamia Super Deli (270 Marrickville Rd), where they've wedged a king's ransom in cheese and meats into the glass counters and the fridges are stocked with house-made dips (the taramasalata is particularly good). Top tip: you can apply those dips to the souvlaki skewers from Souvlaki Boys (179 Marrickville Rd), making dinner a fast and delicious cinch.

DRINK For truly local vibes, cheap-but-good cocktails and can't-resist toasties, the Marrickville Hotel (244 Marrickville Rd) is an ideal place to settle in for an arvo. If vino is your vice and you're particular about your wines you'll find natural and new world drops in casual, non-pretentious surrounds at Where's Nick (236 Marrickville Rd), a little wine bar with a lot going for it. 

DO If you're looking for live music, you've come to the right street. You can catch gigs galore at Lazy Bones Lounge (294 Marrickville Rd), Camelot Lounge (Cnr Marrickville Rd & Railway Pde) and Gasoline Pony (115 Marrickville Rd), and even more live performances at the Factory Theatre on nearby Victoria Rd.

Discover the best of the neighbourhood: a local's guide to Marrickville.

Sydney’s historical and spiritual home for the LGBTQIA+ community undoubtedly centres around the ‘Pink Mile’ of Oxford Street. On the Darlinghurst end, you’ll find the city’s main drag of gay bars and nightlife venues – a stretch that has featured in every Sydney Gay and Lesbian Mardi Gras parade since 1979 (with the notable exception of 2021, when the parade was relocated to the SGC). Beyond Taylor Square, as you enter the des-res neighbourhood of Paddington, the street shifts into a very different gear. Here you’ll find some of the swankiest boutiques in the city, where bespoke fashions and high-end homewares make for some of Sydney’s most luxurious retail experiences.

EAT Josh Niland's revolutionary gill-to-tail approach to seafood has made Saint Peter (362 Oxford St) one of the most hallowed food destinations in Sydney. During the national shutdown in 2020, the restaurant underwent a major overhaul, giving the space an open plan concept that allows diners to see this culinary magician revealing his tricks. 

DRINK During the six years of the lockout era, Oxford Street lost a bit of its sparkle. Under the stranglehold of the wildly unpopular nightlife regulations, the carefree spirit that made this strip such a late-night playground began to wane and punters slowly dwindled. However, Oxford Street’s Darlinghurst end is now enjoying a welcome renaissance, and venues are taking full advantage. Two new rooftop bars, at the Burdekin (2-4 Oxford St) and the Columbian Hotel (117-125 Oxford St), are a signal that post-lockouts and lockdowns, this happening ‘hood is ready to get the party started once again.

DO Live music is also enjoying a comeback in Sydney, and one of the city’s most trusted gig venues, the Oxford Art Factory (38-46 Oxford St), is proof positive. Here you can discover some of Sydney’s hottest indie talents every week, Wednesday to Saturday. 

Discover the best of the neighbourhood: a local's guide to Paddington.

The hospo heart of the Inner East is a stretch of Sydney that all foodies worth their salt will be familiar with. Along the 1.5km from its boundary with Darlinghurst at Oxford Street to its end at Cleveland Street, you’ll find the world on a plate, courtesy of Crown Street’s eclectic, multicultural mix of eateries, bars, pubs, cafés and speciality grocers.

EAT With such a rich array of restaurants to sample here, there could never be just a single recommendation for Crown Street. If you’re looking for an affordable feed with flavour that punches well above its price tag, Pizza Fritta (428 Crown St) on the corner of Crown and Foveaux is the go. It has become one of the neighbourhoods most popular casual diners since opening in 2019. Mid-level budgets are best spent at stylish Indian eatery Foreign Return (527 Crown St), a relative newcomer to the street that has already earned a major following. If you’ve got money to burn, the extraordinary menus at mod-Japanese Toko (Unit 3, 490 Crown St) or Middle Eastern fine diner Nour (Unit 2, 490 Crown St) will happily help you part with your cash in exchange for some of the best eating in Surry Hills.

DRINK Every good neighbourhood needs a good pub, and on Crown Street, that also happens to be one of the best boozers in the city. The Clock Hotel (470 Crown St) is a Surry Hills institution, serving the good people of Sydney since 1863. Of course, it’s had more than a few facelifts in the century-and-a-half since it first rolled out the barrels, and its current incarnation has carefully carved up the pub's large footprint to create a series of intimate spaces and discreet bars. Prime position has to be on the balcony overlooking the street: pints and people watching FTW.

DO While the company may be a Victorian import, the Gin Lab at the Four Pillars micro-distillery (410 Crown St) feels right at home amongst the drinking dens and dining destinations of Crown Street. Book in for a Martini masterclass and learn to master the subtle complexities of this classic cocktail. 

Discover the best of the neighbourhood: a local’s guide to Surry Hills.

It may not quite be the grungy counter-culture hub it was a couple of decades ago, but the gentle gentrification of Newtown’s major artery has done little to dull its indie creds. If Bondi is a morning town, King Street is where Sydneysiders flock after dark, thanks to its densely packed pub and bar offering, excellent live music venues and a curious collection of restaurants (ranging from cheap Thai for under a tenner to higher-end foodie destinations). Whether you’re after a knees-up, a hot date, a pre-show bev or dinner after the credits have rolled, King Street has a perch for every kind of night owl.

EAT The Finnish-Italo-Australian food at Cafe Paci (131 King St) has to be some of the city’s most creative cooking and well worth the wait for a table. 

DRINK Earl’s Juke Joint (407 King St) ranks as one of the most unerringly excellent cocktail bars in Australia, let alone on King Street. Head down for exacting classics or brazen creative flair, set to an old-school bluesy soundtrack.

DO Want to piss off your folks? Just been through a break-up? Midlife crisis? Just fancy a change? Whatever the reason, the place to get something pierced, implanted or inked is Industrial Strength Body Piercing Studio (192 King St).

Discover the best of the neighborhood: a local’s guide to Newtown