Things to do in Sydney in May

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...

The opening note of ‘The Circle of Life’ may just be one of the most recognisable in a Disney musical. If you don’t agree, then you may have to convince the entire theatre-going audience who were at Disney’s The Lion King on opening night. The full house’s roars could be heard all the way out of the Capitol Theatre’s front doors as the king of musicals triumphantly returns to Sydney – the first time in more than a decade. What type of show is The Lion King? It’s called The King of Musicals for a reason. If it’s not Elton John’s iconically recognisable music, or Tim Rice’s lyrics you’ve sung over a late-night karaoke session, then its Roger Allers and Irene Mecchi’s book featuring the characters you love, the characters you hate, and the ones you undoubtedly cry over – tears were definitely still shed during that scene. What’s so beautiful about The Lion King is the blurring of worlds and culture that merges in between all of these. Julie Taymor’s directorial conception blends African culture, language, movement and costume underneath masks and puppetry of the animal characters. Mufasa’s “crown” is a stoic, strong and towering headdress. The elegant lionesses soar and leap through the sky through Garth Fagan’s choreography as wing-like gowns flow behind them. The animals of Pride Rock are adorned with larger-than-life puppets of intricate designs and architecture: a re-engineered bicycle becomes leaping antelope, birds fly above the crowd on poles manipulated by performers,...

Love, for all its risks, is rarely framed as something unsettling or dangerous. Desire, hope and care are often gathered together in pursuit of joy. Though sometimes what emerges is darker: love can shift your sense of self, clouded by danger, deceit and dread. The River, directed by Margaret Thanos, explores the space between desire and deceit in an evocative introspection on love. Written by Tony Award-winning playwright Jez Butterworth, the production forces the audience to confront not only what love reveals, but what it conceals. What is the premise of The River? The Man (Ewen Leslie) and The Woman (Miranda Otto) spend a weekend together at his remote cabin by a river. He is eager to share a particular fishing expedition with her – one that can only happen at night, with no moon. As the play unfolds, what begins as ripples of a tender, romantic escape becomes more uncertain – an estuary sifting through contradiction, manipulation and honesty. The production never fully decides what it wants to be – a romance, a tragedy, or something in between. While these questions linger, Thanos’s creative vision allows the ambiguities to become an asset, giving the audience space to remain in the uneasy territory between desire and distrust, where each confession feels both revelatory and suspect. Rather than resolving its tensions, the production lets them pool and deepen, leaving the audience suspended – albeit a little too long – in its murky emotional currents. Who are the cast...

Thought-provoking. Boundary-pushing. Unapologetically disruptive. The elusive yet world-famous street artist Banksy has another exhibition coming to Sydney. If you missed the chance to see The Art of Banksy: Without Limits at Sydney Town Hall in 2024, you’re in luck. Banksy Limitless opens at The Rocks (155 George Street) on April 1, 2026 for a limited season, following a sold-out run in London.  This new showcase features more than 250 works, large-scale installations, sculptures, digital displays – plus an impressive state-of-the-art hologram experience. Visitors can uncover untold stories behind iconic works including Cinderella at Dismaland, London Zoo and Ice Cream Van, while immersive rooms and bold visual storytelling invite audiences to step inside Banksy’s provocative universe. Renowned for his sharp wit and unflinching social commentary, Banksy continues to challenge perspectives on politics, culture and human rights. In keeping with his humanitarian ethos, a portion of proceeds from Banksy Limitless will support the M.V. Louise Michel, an independent high-speed lifeboat rescuing migrants in distress. So much more than a traditional exhibition, Banksy Limitless is a powerful, multi-sensory experience that will pull you in. Don't miss it.  Ticket prices are from $42 for adults, $30 for children. Get your tickets 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....

Anastasia (1997) was among the first musical films I knew in its entirety. While many children frolicked to Timon and Pumbaa’s playful anthem in The Lion King, I was instead reenacting “Once Upon a December” in my living room, captivated by a heroine whose quiet determination carried her through danger and uncertainty. At the time, I could not have anticipated how deeply this film would shape my relationship with musical theatre. “Journey to the Past” soon became a staple audition piece, and Anya’s unwavering belief in her own worth quietly informed my own developing sense of confidence.  What I did not yet understand, however, was the historical context behind the story: the execution of the Russian imperial family in 1918 and the long-standing myth that Grand Duchess Anastasia Romanov survived. The 1997 animated film leans fully into fantasy, using magic and spectacle to distance itself from historical reality. The stage musical, which premiered on Broadway in 2017 with a book by Terrence McNally and music and lyrics by Stephen Flaherty and Lynn Ahrens, takes a different approach, removing the supernatural elements in favour of a more realistic political setting. This creative decision has lingered uneasily over the production since its premiere, inviting criticism for its revisionist narrative – a species of theatrical “fake news,” further undermined by the musical’s questionable commitment to American accents. In performance, now at Sydney Lyric Theatre, this shift...

As the nights grow colder and my toddler at home seems permanently on the brink of the next illness, the effort it takes to leave the house can feel outsized. There is comfort in staying put, wrapped in something soft, conserving energy for the long nights ahead. What tempts me out anyway is the possibility that a show might meet me where I am (usually tired, frayed, vulnerable) and change my mood or shift my mindset. Gutenberg! The Musical!, now showing at Hayes Theatre, does exactly that, reminding me how deeply restorative it can be to laugh, to be surprised, and to feel briefly, gloriously lighter. What is the premise of Gutenberg! The Musical!? Gutenberg! The Musical! centres on two hopelessly enthusiastic writers, Bud (Ryan Gonzalez, In The Heights) and Doug (Stephen Anderson, Titanique), who have created a loose, logistically impossible musical about the life of Johannes Gutenberg, the inventor of the printing press, and are desperate to get it produced. The premise is gleefully meta: the audience is positioned as a room full of potential Broadway producers invited to a showcase, while the two performers play not only themselves but every role in their historically questionable show. Armed with nothing but baseball caps to signify characters and an unwavering belief in their own genius, Bud and Doug’s earnest ambition drives the comedy, as the musical becomes less about Gutenberg himself and more about the absurd, scrappy devotion of theatre-makers willing to do...

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...

Few songs embed themselves into the cultural DNA quite like Jeff Buckley’s cover of “Hallelujah”. While younger generations are discovering his talent through TikTok, Oscar-nominated filmmaker Amy Berg, who grew up on the grunge and punk of the ‘90s, revisits his life in a tender new documentary It’s Never Over, Jeff Buckley. Pieced together through curated footage of the late singer-songwriter both onstage and off, the documentary is told in large part by the women in his life. We hear from his single mother, Mary Guibert, his good friend Aimee Mann, his former girlfriend Rebecca Moore, and his longtime partner Joan Wasser, who each offer emotional memories and thoughtful insights.  What’s undeniable through their recounts is Buckley’s talent, as Time Out reviewer Elizabeth Weitzman writes: “The punk angel with the four-octave range also had a rare and remarkable mimetic gift – which made him an unusually skilled interpreter of other artists, from Nina Simone to MC5 to Nusrat Fateh Ali Khan.”  Whether you know him for the myth forged by his untimely death – echoing that of his musician father, Tim Buckley – or for his elegiac take on Leonard Cohen’s “Hallelujah,” a rendition that has moved millions, It’s Never Over, Jeff Buckley offers another side of the story. “Fans, of course, will fiercely argue that Buckley has so much more to offer. And in the strongest compliment to Berg’s affectionate portrait, she makes a similarly convincing case, with ample and tender grace.”...

If you've ever wondered what would happen if a kid's drawing of their wildest dream utopia suddenly came off the page and into real life, you're in luck, because that's pretty much what's happening right now beneath the Art Gallery of NSW.  Artist and professional disruptor Mike Hewson has taken over the weird subterranean world of The Tank with his one-of-a-kind new exhibition, Mike Hewson: The Key's Under the Mat, where for the first time ever, all the main lights in the normally pitch-dark Tank will be switched on, revealing a weird wonderland of interactive art pieces and play equipment that have to be seen to be believed. We're talking: A steam room with stained glass windows that you can actually sit in, a functioning sauna with bespoke church pews, five actual operating public barbeques that you can cook on, rushing water to play in (seriously, bring your swimmers), a working laundry,  and a free-to-use recording studio, plus a whole plethora of bright and delightful surprises that are all about getting community together, to do cool stuff, for free. Basically, break your imagination and delete all adult expectations. This is unlike anything we've ever seen.  Kids who aren't afraid of some risk are also one of Hewson's big targets with this show (although parents, rest easy, the floor is specially made out of recycled soft rubber that's rated for use in public playgrounds), with the space also home to a wild children's playground. Intrepid kidlets can test their...

Can’t wait until Vivid to get your fix of luminous fun? We’ve got you. From May 8 to June 14, the outdoor light show known as Glow is coming back to Western Sydney’s Sydney Zoo – and for its fifth year, it’s going bigger, brighter and a whole lot more immersive. The reimagined night trail transforms familiar enclosures at the zoo into glowing, atmospheric scenes – with large-scale light installations and layered soundscapes guiding you through a completely different world after dark. The headline act this year is the Luna Light Journey – an all-sensory experience curated by Laservision (the team behind some of the country’s most impressive light-based artworks, including Echoes and Scenic World’s Nocturnal). Expect an extended illuminated trail along the boardwalk and plenty of interactive moments as you wander through the forest of colour and sound. It’s part art installation, part night safari – designed to keep all ages entertained. Beyond the light trail, there’s a carnival-style precinct at the entrance of the zoo (open even if you’re not heading into Glow), plus food and drink options to keep things cosy as the temperature drops. With more than 100,000 visitors heading to Glow last year, this one tends to sell fast – so you’ll want to book tickets ($35 for adults, $19.99 for kids) ahead of time.You can learn more and book over here.Stay in the loop: sign up for our free Time Out Sydney newsletter for more news, straight to your inbox.RECOMMENDED: Want fun now? Here’s...