The best gigs to see in Sydney this winter

Get to Darling Harbour on Sunday, March 1 and say 'Opa' to the Greek Festival of Sydney. It's free, it's fun and it's filled with all your Hellenic favourites. Now in its 22nd year, this celebration of Greek-Australian culture will have Tumbalong Park buzzing from 10am to 10pm.  Feast on yum souvlaki and syrupy loukoumades, watch different dance troupes perform traditional Greek dances like the Sirtaki (yes, the same one in Zorba the Greek) and the Kalamatianos (in a circle) and let the kids enjoy face painting while you browse the many pop-up stalls for handcrafted trinkets. There'll be live music, entertainment and dancing throughout the day. And at 7pm, singer Ioulia Karapataki will perform directly from Greece, so make sure to catch that.   Learn more about the Greek Festival of Sydney and plan your visit here. Stay in the loop: sign up for our free Time Out Sydney newsletter for more news, travel inspo and activity ideas, straight to your inbox. RECOMMENDED: Jetstar has just dropped a huge sale with international flights for less than $200 NSW will get 24,000 more trees thanks to a $10m tree planting program Wowsers – the median house price in Sydney is now $1.76 million

Sydney’s fave foodie playground is about to step up its entertainment offering. The new Sydney Fish Market’s New Wave Concert Series kicks off this Feb, transforming the architecturally impressive foodie mecca into a harbourside stage for three golden-hour Saturdays. From 5pm-8pm for the next three Saturdays, visitors can pair fresh seafood with live performances from some of Australia’s brightest emerging talent. The best news? It’s completely free – meaning more cash left over for sashimi.RELATED READ: These are our fave waterfront restaurants in the city Across the three-night series, we can expect a mix of genres: February 21 brings big country-folk energy, February 28 leans into indie dream-pop, and the March 7 line-up will feature a fusion of R&B, jazz and indie pop. Headliners include powerhouse rock duo Big Wheels, disco-funk faves Bread Club, and indie-pop angel Yorke. Each gig will be steered by Ifeoma (Ify) Peace Obiegbu, the South West Sydney-based creative, poet and storyteller with a knack for making every mic moment feel electric (you might know her from her stint as host of FBi’s Up For It!, where she spent two years championing local talent).If you ask us, it’s the perfect excuse to eat oysters in the open air and people-watch as the sun drops over Blackwattle Bay. As you’d expect, there’s no need to book or register – just rock up with an appetite between 5 and 8pm.RELATED READ: These are our fave things to eat at the new Sydney Fish Market Stay in the...

The Twilight at Taronga 2026 Summer Concert Series ticks off a hefty amount of Sydney summer ideals – harbour views at dusk, alfresco live music and a zoo-fringed lawn to sprawl out on with shared treats and mates. Add in a diverse line-up of top Aussie artists, and you've got yourself a pretty great way to spend a waterfront sunset.  Running over five back-to-back weekends from February 6 to March 7, Twilight at Taronga will complement the growls, roars and hisses of the menagerie with old-time faves and newer artists. Things kick off on February 6 with indie folk-rock band The Paper Kites, followed by every toddler's favourite Emma Memma who's performing for 'Lil’ Twilight' – a special morning shows at 10am on February 7. February 20-22 is all about performances by singer, songwriter, musician and multi-instrumentalist Xavier Rudd. Other drawcards include Sons of the East, Vera Blue, The Reubens, Dope Lemon and more, ending with Bjorn Again on March 7 (yep, it's sold out already).  What's more, every ticket purchased before Christmas will go into the draw to win an overnight stay at Taronga Zoo’s Roar and Snore for two, valued at $800.  Every ticket does more than give you a fun night out – it helps protect Australia’s precious wildlife. By attending Twilight at Taronga, you’re supporting the Wildlife Veterinary Teaching Hospital that provides care for thousands of animals. Ticket prices start at $79 for adults, and you can add on optional extras like picnic rugs,...

If there’s one thing Sydney does spectacularly well, it’s slow summer evenings – the kinds that see the sky turn sherbet-pink and the whole city look a little softer around the edges. This summer, Cockatoo Island/ Wareamah is handing us a very solid excuse to make the most of it: Sunset Sessions is back, taking over the lawn of historic Biloela House with a weekly dose of live music in the open air. Running on Saturday evenings from January 10 2025 to April 4 2026, the island’s curated open-air gig series is one of those annual events that reliably sells out – and for good reason. The formula is foolproof: pack a picnic rug, stretch out on the grass and let a line-up of emerging local artists soundtrack the slow fade into night as the sun sets behind the city. RELATED READ: These are the best sunset spots in Sydney This year brings a particularly juicy mix of genres and rising talent to Sydney Harbour’s largest island. Expect lush vocals from Charlie Collins, dreamy pop by Mia Lovelock, and globe-spanning grooves courtesy of Immy Owusu and Dom Diaz. You’ll also catch Merpire, Joel Leggett, William Alexander, Dave Graney, Joe Mungovan, Clay Western, Cooee and Luke Saunders – with more artists still to be announced. If you’re not the type to pack your own snacks, Biloela House will have refreshments ready to go – or you can pre-order a hamper of treats when you book your ticket. And if you’ve ever entertained the fantasy of running away to an island for the night, Cockatoo...