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A man watching the Vivid Sydney lights from across the hardbour
Photograph: Destination NSW

Things to do in Sydney in May

The temperatures outside may be dropping, but things are really hotting up in the city during the last month of autumn

Maxim Boon
Written by
Time Out editors
&
Maxim Boon
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It's no secret that Sydney shines during the summer. But that's not to say that the colder months aren't also packed with good times in the Harbour City. May is chock-full of festivals, shows, exhibitions, pop-ups, markets, parties and other fun happenings, including the return of Vivid, after a two-year hiatus.

Don't forget to treat your mum to a day she'll remember on Mother's Day, May 8. We've put together a bunch of ways that you can spoil her rotten, from a swanky high tea, to a pampering at a spa, or even just a beautiful bunch of blooms from one of Sydney's finest florists.

Get your culture fix with our pick of the very best theatre and art to see this month.

The best things in May

  • 5 out of 5 stars
  • Theatre
  • Musicals
  • Elizabeth Bay

Blood, sweat, tears, thumbtacks, rollicking rock ballads, questionable costumes and a fully ocker vernacular – this show has it all. Dubbo Championship Wrestling (DCW) is absolutely over the top, and it’s just about the most bloody fun you can have on a night at the theatre.  Rose (Zoe Ioannou), a young woman who grew up in Dubbo with wrestling in her blood, has long ago turned her back on the family business and Dubbo’s stifling smalltown ways. When circumstances lead her back to her hometown on the eve of Dubbomaina, the biggest wrestling tournament of the year, Rose is drawn into a monumental smackdown over family and identity. There are three things that can undo any musical: drawn-out songs that don't further the story, central romances with no palpable chemistry, and second acts where the action stalls and the audience gets bored. DCW powerfully gut punches all those potential pitfalls, pulls a cheesegrater out of nowhere, and goes back for seconds.  Each and every one of the performers on stage commits to their larger-than-life character with just the right amount of earnestness (including the on-stage rock band and the techie in the “Dubbo TAFE” T-shirt). I say “larger than life”, but if you’ve ever spent time with people who live outside the metropolitan centres, these “cashed-up bogans” don’t feel like too much of a reach.  Ellen Simpson’s (Little Shop of Horrors, Dream Lover) choreography and Tim Dashwood’s (Julius Caesar, Death of a Salesman) fight direction are p

  • Things to do
  • Chatswood

Revel with family and friends this autumn as Willoughby City Council treats Sydneysiders to 23 days of fun curated specially to remind us of Chatswood’s rich, colourful and vibrant culture. Starting on May 6 and running right through until May 29, Chatswood Nights features a food trail that pays homage to the local businesses affected by the pandemic while also celebrating the diversity of the suburb’s food precinct. From Korean to Malaysian and North American bites, you’ll be spoiled for choice.  Prepare to be transported to Paris, Rome or Barcelona as different artists playing world music take to the stage every Friday as part of the Chatswood Live at Night program.  And you won’t want to miss the world-class 3D animation projection created by Limelight (a Hungarian 3D projection-mapping team) and Ukrainian refugee animator Svetlana Reinish. It will light up the Concourse Concert Hall facade nightly, and follows the journey of a gnome escaping its garden to explore the world. That’s not all – follow the map of discovery to find 12 giant lit-up inflatable gnomes scattered throughout Chatswood’s key public spaces. They all have their own unique personalities, and are inspired by the suburb’s ethnic diversity. Snap yourself with the gnomes to enter the Roaming Gnomes competition, with a massive $20,000 in prizes up for grabs. The more gnomes you visit the more chances you have to win. Chatswood Nights is all about community, inclusivity, good vibes and even better food. For mo

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  • Art
  • Galleries
  • price 0 of 4
  • Sydney

Australia’s favourite portrait prize is back for 2022, and as always it's a delight to see which famous faces have made it into the mix of painterly interpretations. This year over 800 paintings were submitted, and you can peruse the top 52 at the Art Gallery of New South Wales until August 28, when they ship off around the country. This year Koori artist Blak Douglas took out the top gong, the $100,000 Archibald Prize, for a painting of his good friend and fellow artist Karla Dickens, depicted looking grumpy and holding leaking buckets as she stands in muddy water during the recent devastating floods in her hometown of Lismore in northern New South Wales.  The much-anticipated Packing Room Prize, which is judged by the Art Gallery staff who receive, unpack and hang the entries, was awarded this year to Sydney-based artist Claus Stangl for his impressive 3D-style painting of beloved New Zealander writer, director, actor (and everyone’s crush) Taika Waititi. A highly commended honour was awarded this year to Sydney artist Jude Rae for her portrait of scientist, engineer and inventor Dr Saul Griffith. Rae is also a finalist in this year’s Wynne Prize with her landscape The white fig (Ficus cirens), Royal Botanic Gardens, Sydney. Other notable portraits this year include a colourful depiction of Shane Jenek standing shoulder to shoulder with his drag alter-ego Courtney Act, a realistic painting of actor Hugh Jackman posed with his wife Deborra-Lee Furness, a cheeky lounging nude

  • Music
  • Rock and indie
  • Parramatta

Singer, songwriter and composer Martha Marlow has made waves amongst the industry thanks to her arresting vocals, poignant lyricism and cinematic orchestral arrangements. The Sydney-raised artist was recently shortlisted for the 2022 Australian Music Prize, Triple J's Richard Kingsmill labelling her “one of the year’s best kept secrets”. It's only a matter of time before the rest of the world cottons onto Marlow – a polymath who includes landscape painting among her accomplishments – and now you have the opportunity to see her live at Riverside Theatres' Sunday afternoon music series. On May 29 at 4pm, Martha and her band (which includes a string quartet) will perform songs from her ARIA-nominated debut album Medicine Man at Parramatta’s beloved performing arts centre. Visit Riverside Paramatta to book tickets.

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  • Things to do
  • Bungarribee

It may be time to start screaming hysterically (with joy) because Sydney Zoo is set to become the brilliantly lit, glow-in-the-dark backdrop for Glow, a massive light festival that will very possibly blow your socks off – or at the very least, give you a wintery night filled with far more neon rainbows and glow tunnels than usual.  Think Vivid, but add in a sparkly ice rink, glowing carnival rides and Australia’s biggest reptile and nocturnal animal house. Like, it’s pretty good. (Taronga isn't the only zoo getting in on the glowing nighttime action). This interactive experience will be on at Sydney Zoo in Bungarribee, Western Sydney, from May 13 to June 5. You'll be able to explore this new zoo after dark while also getting to twirl, whirl and swirl your way around a number of wild and incandescent night activities that are perfect for the whole family, with the zoo having undergone a magical, fairyland-esque transformation bound to delight anyone who sees it.  Get ready to follow a luminous light trail filled with interactive installation pieces, ride on a giant Ferris wheel and skate on a twinkling ice rink – all while guzzling an iridescent variety of food and drink in the presence of a number of exotic animals that you normally only get to glimpse in the controlled light of day.  This bright night out has been designed to be as accessible as possible (no steps or hills allowed) and will be open each night from 5.30-9.30pm. Tickets are $25 online and $30 at the gate, whil

  • 4 out of 5 stars
  • Theatre
  • Musicals
  • Sydney

A magnificent piece of stagecraft opens the orchestral work-turned-movie-turned ballet-infused musical theatre show An American in Paris. Jonathan Hickey sits alone at a spotlit piano dwarfed by the darkness of the theatre. He portrays Adam Hochberg, our narrator, an American Jewish man and gifted musician with a wounded leg and heart. He reminds us that while the war may be over, with Paris of 1945 finally liberated, there’s no magic switch to make everything right after this nightmarish cataclysm. The city is still standing, but its citizens are starving and great swathes of the country lie in ruins.  Setting the scene for us, Adam and his piano are then magically whisked away as the first jaw-dropping use of the production’s vast digital sets bathes the theatre in hellfire. The terrifying red of Nazi flags that sweep upwards to the heavens are seconds later pulled down and replaced by the Tricolore. This digital iteration, conjured by set and costume designer Bob Crowley, is seamlessly replaced by a physical French flag borne aloft by the gifted (and marvelously attired) ensemble. Suddenly, the computer-generated backdrop depicts a phalanx of five fighter jets flying high over l’Arc de Triomphe.  This moment is our goosebump-inducing introduction to dashing star Robbie Fairchild. He plays American GI Jerry Mulligan – famously depicted by Gene Kelly in the Oscar-laden 1951 movie by Vincente Minnelli – who turns to the audience with a jaunty salute. Fairchild, a former princ

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  • Museums
  • History
  • Circular Quay

Ready to cross over to the dark side? Then After Dark at the Justice & Police Museum is the place to be. Guided by guest speakers, artists and performers, you’ll immerse yourself in Sydney’s depraved world of crime, social alienation, indecency and the occasional miscarriage of justice.  Running 5-8pm most Fridays from May 6 to June 24, 2022, this after-hours series promises a unique way to kick off your weekend down at Circular Quay. Bookings are essential, so check out the event details below and grab your tickets while you can. Sly Grog: Razor Gangs When: May 6 & Jun 10 With alcohol sales heavily regulated in the early 20th century, Sydney’s gangsters made a fortune by unlawfully selling liquor, known then as ‘sly grog’. Opt for the May 6 session and you’ll be guided on a journey back in time to the 1920s and 30s by Larry Writer, journalist and author of Razor. Learn about the dark history of these bandits as Writer details the history of sly groggers and razor gangs through these periods. If you attend the June 10 event, historian and raconteur Max Burns-McRuvie will bring to life the sensational stories behind the bordellos and 'bruisers' of Sydney in the 1920s and ‘30s.  Tickets are $30 each and include a cocktail on arrival, museum entry and access to all the entertainment. Book now Femme Fatale  When: May 13 & Jun 17 You know what they say: well-behaved women rarely make history. Sexy, sinful and deliciously dangerous – it’s time to delve into the facade of the ‘femm

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  • Things to do
  • Fairs and festivals
  • Sydney

Vivid is back. No really, we mean it this time! Sydney’s ill-fated flagship winter festival of lights, entertainment and ideas has had a rough couple of years, with its 2020 iteration cancelled due to the first lockdown, and then its 2021 program, which had been billed as its triumphant return with a line-up bigger than any previous outing, was derailed by the Delta surge that thrust the city into another large scale lockdown for more than quarter of a year. After such a long hiatus, the return of this familiar stalwart of Sydney’s cultural calendar is ready to make up for lost time, with a program on a scale never before attempted by Vivid. Which stands to reason, given that this is the debut program from Vivid’s latest director Gill Minervini, who clearly hopes to make a good first impression on the Sydneysiders who have been fangin’ for the fest for more than two years. The festivities commence on May 27 through to June 18, with mesmerising art displays, 3D light projections, uplifting live music performances and deep-dive discussions lighting up 11 locations over 23 nights.  The longest continuous light walk in Vivid history will illuminate the Sydney foreshore, stretching over eight kilometres, linking the Sydney Opera House to Central Station, with more than 200 LED sculptural birds guiding the way as part of the Future Natives installation. “Vivid Sydney’s Light collection features work from a vast array of artists, from the renowned Ken Done and Ramesh Mario Nithiyend

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  • Art
  • price 0 of 4
  • Barangaroo

This year marks the first time that the Cutaway – the cavernous, below-ground concrete space used for large-scale events underneath the Barangaroo headland – has been used as a venue for the Biennale. It's a match made in edgy, arty, below-ground heaven, and it has all the earthy industrial chic of Cockatoo Island, without the ferry ride. An open-air valley along the edge of the space allows outside air to flow through and any rain to thunder down beside you without disturbing the artworks or perusers. Take your time exploring works from some 25 artists and participants, and relax with a drink and a snack in the pop-up bar with refreshments provided by P&V, Mary’s and Campari.  A huge site-specific and immersive bamboo installation weaves its way throughout the architecture of the Cutaway and the other artworks contained there. Spanning 600m2 and inspired by the flow of a river, Flow is the largest project ever undertaken by Sydney-based multidisciplinary studio Cave Urban, and one of the largest bamboo structures ever produced in Australia.  Kick off your shoes and curl up on the rug to soak up Pink Steam, a film and sound installation by Blue Mountains duo David Haines and Joyce Hinterding. Filmed on the Fish River in Wiradjuri country, specially modified radioactive cameras reveal parts of the spectrum that transmit beyond visible light. Mexican artist Tania Candiani presents a hovering sculptural sound installation. The sculpture appears as branches, symbolising waterway

  • 4 out of 5 stars
  • Theatre
  • Drama
  • Dawes Point

In early June of 2020, playwright and actor Meyne Wyatt delivered a performance on ABC’s Q&A that was hailed as a watershed wake-up call to the reductive ways First Nations people are misrepresented and commodified through the white gaze. This blazing monologue, an excerpt from City of Gold, became an instant viral moment, not only for the content's raw truth but also for its delivery's gut-punch power. But as urgent and sobering as this speech is in isolation, it gains an extra dimension of emotional heft within the context of the story from which it's lifted. Wyatt’s debut play, which premiered in 2019 at Sydney’s Griffin Theatre before touring across the country, offers the experience of a grieving family as the microcosm to unlock a much broader discussion about identity and discrimination. Preservation of culture, the struggle to hold onto country and community, and the myriad entrenched systems of violence and mistreatment faced by First Nations people are brought into harrowing focus through the fractious relationship of three siblings struggling to cope in the wake of their father’s death. The play opens with a warped vision of Aboriginality, a figment of colonial myth that still persists as true blue Australiana today. Breythe Black (Wyatt) is an actor on the set of an ad promoting lamb for Australia Day barbies, spear in hand and a canoe at his feet. While the storyline claims to be about unity and reconciliation, its hamfisted imagery is offensively white-washed. B

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