The best gigs to see in Sydney this winter

Vivid Sydney is back in action, but it’s not just the sparkly lights and foodie offerings that have caught our attention. The Vivid Music program is back with a vengeance, and between free outdoor concerts, exclusive gigs, sweaty dance parties, iconic international acts and local legends, there’s a whole lot of noise to get around.  We've done the browse work for you and unearthed the acts, venues and big nights out you should put your coin behind (or even enjoy for nix). Take your pick, and light up your winter with one of these bespoke gigs going down between May 23 and June 14. Photograph: Anna Kucera | Ayesha Madon Tumbalong Nights will return to Darling Harbour, with free entertainment hitting the outdoor stage every night. DJs will keep the party going from Sunday to Wednesday, while live music starts at 7.30pm every Thursday to Saturday (plus Sunday 8 and Monday 9 June for the long weekend), with kids’ shows from 5–6pm on Saturdays. Rising star and Time Out Sydney cover girl Ayesha Madon will kick things off, sharing a double bill with fellow Sydney pop singer Charley (Fri, May 23). The free concert series also features local surf-rock darlings Winston Surfshirt, Sydney rockers Body Type, V-Pop sensations Mỹ Anh and Chi Xê, Grammy-winning African artist Dobet Gnahoré, Stella Jang from Korea, India’s Zaeden and former bass player for Prince, MonoNeon. (Check out all the acts and dates over here.) Photograph: SOH/Dean Tirkot | Lady Fur for House of Mince At the...

Just as winter begins to rear its head in the Emerald City, the annual festival of lights, music, ideas and more rolls around: lighting up the city with a multidisciplinary program that gets bigger and brighter every season. Vivid Sydney 2025 is no exception, with a glittering program of lights, music, food and ideas that’s not only sparkly, but surprisingly subversive. Inspired by the theme of Dream, Vivid Sydney 2025 will use art and experience to interrogate and expand our understanding of what it means to dream: literally and figuratively. From Friday, May 23 until Saturday, June 14 2025, expect the city to be transformed into a glittering wonderland of art, inspiration and ideas – with Vivid’s signature light displays acting as a vehicle to usher in a boundary-pushing series of events. This year’s program features thought-provoking discussions, insightful film screenings, immersive street kitchens, interactive artworks and so much more. This year, Vivid-goers can expect a redesigned festival footprint, with the (totally free) light walk being presented across five distinctive zones including eight buildings and landmarks that have never been illuminated before (as well as the return of some old favourites, like Martin Place). For Vivid Sydney 2025, there’s also an expanded Vivid Music program (with Vivid Live returning to the Opera House with big names including Sigur Ros, Marlon Williams and Ezra Collective. We can also expect an interactive Stranger Things...

To bring a little musical joy to the Harbour City through the cooler months, Sydney’s historic waterside precinct The Rocks is hosting free jazz performances every Thursday throughout autumn and winter – with live performances by musicians from around Australia. Jazz Sessions in The Rocks will run from 6pm until 8.30pm every Thursday from Thursday, April 3 until Thursday, September 25 – so there’s plenty of time to catch the star-lit shows.  Want to keep the music going? From 8.30pm until 10.30pm every Thursday, ocal distillery Hickson House Distilling Co  will be hosting a later-night jazz set, and serving up an excellent dinner deal: $35 for a signature cheeseburger and fries, paired with a masterfully crafted gin and tonic. The line-up so far includes harmonic duo Aaron Flower and Kate Wadey, the dynamic vocalist Leah Berry and Sydney-based ensemble Zodiac Quartet.The events are free to attend and there’s no need to book. You can learn more over here. Stay in the loop: sign up for our free Time Out Sydney newsletter for more news, food & drink inspo and activity ideas, straight to your inbox.   RECOMMENDED:  Want more evening entertainment? These are the best bars and pubs in Sydney for live music. And these are the best shows to catch in Sydney this month. Need fun now? Here’s what’s on in Sydney this week