The best gigs to see in Sydney this winter

To bring a little musical joy to the Harbour City through the cooler months, Sydney’s historic waterside precinct The Rocks is once again transforming Thursday evenings into a free, open-air jazz experience – with Jazz Sessions in The Rocks returning for its third year in 2026. Running from Thursday May 7 until Thursday September 24, the series will take over The Rocks Square each week, delivering intimate live performances set against cobblestone laneways and heritage buildings in the heart of Sydney. Curated in partnership with SIMA (Sydney Improvised Music Association), the program spotlights Australia’s thriving contemporary jazz scene, with a rotating monthly line-up of artists. The opening month features standout acts including the Harley Coleman Trio and Billie McCarthy, with new performers announced at the start of each month to keep things fresh, spontaneous and ever-evolving. Event times (every Thursday) 6:30pm – 7:15pm – First set 7:15pm – 7:30pm – Interval 7:30pm – 8:15pm – Second set 8:30pm – Event concludes To complement the music, visitors can explore a range of nearby food and drink offerings across The Rocks, from fiery Thai at Snake Bark, freshly shucked oysters at Hooked & Harvest, and classic Italian at Sicilian. Pisa Slice will also be serving a $10 slice and soft drink combo every Thursday, while a pop-up bar will be pouring everything from mulled wine to and Spicy Mango Margaritas. Free entry. No bookings required. Sign us up. Find out more over...

If the end of Sydney Observatory’s summer music series has left a hole in your Friday schedule, the 2026 Biennale of Sydney is here to fill it. From 6pm every Friday night for the next couple of months, the Biennale’s Art After Dark program will transform White Bay Power Station into a boundary-blending live music venue – with an impressive line-up of acts set to light up the cavernous industrial space (along with bars serving local pours and food stalls serving up your Friday night feed).Curated by Naarm/ Melbourne-based outfit Liquid Architecture, the first three events will feature the likes of Tujiko Noriko, Mara Schwerdtfeger, Ruhail Qaisar, Marcus Whale, Liam Keenan and Allara Briggs-Pattison. Next up, the Inner West Council will present three more nights of live music, with Body Type, Yes Boone and BOY SODA bringing home-grown talent to the historic Rozelle site. The final three nights, curated by Vivid Sydney, will include ambient techno trio Purelink, French-Senegalese singer-songwriter anaiis, and the festival’s closing night party on Friday, June 12, which promises to be a multi-stage celebration of global music (with extended hours until 11pm). Beyond the Friday night fun (and the art, obvs), the three-month festival will also operate Memory Lane Food Markets every Saturday, Africa Day celebrations, six new performance commissions, guided tours of White Bay’s historic spaces, Family Days, youth and education programs, and access initiatives. Art After Dark will...

When winter rolls around in Sydney, Vivid steps in to bring a little light to our streets for those first chilly weeks. And while Circular Quay sparkles with kaleidoscopic projections, the real magic often happens indoors – on the stages and dancefloors where the festival’s music program comes to life. Keen to plan ahead this year? Two of the city’s most iconic live music venues – Sydney Opera House and Carriageworks – have just dropped the details of their music programs for 2026. From May 22 to June 13, Vivid Live will take over Sydney Opera House, with more than 50 artists lighting up every corner of the World Heritage-listed landmark. Masterful tastemaker Ben Marshall (Head of Contemporary Music at the house) has curated another divinely diverse program spanning genres, generations and geographies – featuring everything from Detroit techno to Arnhem Land surf rock and the one and only Erika de Casier. In the Concert Hall, indie icon Mitski will headline four sold-out nights, performing in-the-round with songs from her new album Nothing’s About to Happen to Me alongside all-time fan faves. Meanwhile, Matt Berninger – best known as the frontman of The National – will deliver a rare, intimate set featuring material from his reflective solo album Get Sunk. Scottish post-rock pioneers Mogwai will celebrate 30 years together with a career-spanning performance, while Yolŋu rock heroes King Stingray make their Opera House debut (indoors at least, they opened for Parcels on the...