Sydney Writers' Festival
Photograph: Supplied | Sydney Writers' Festival
Photograph: Supplied | Sydney Writers' Festival

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

Winnie Stubbs
Advertising

It's no secret that Sydney shines during the summer, but there’s something special about the way the Harbour City turns up its everything-but-the-beach offerings during the cooler months.

This May, we’ve got giggly goodness courtesy of Sydney Comedy Festival, a sparkling line-up of excellent plays and musicals at theatres across the city, Sydney Writers' Festival taking over Carriageworks, a major new exhibition showing at the MCA and free jazz shows in The Rocks every Thursday evening. Oh, and the Archibald.

Adding to the illumination is Vivid 2025 – the immersive wonderland which will be lighting up the city from May 23. Until then, you can get your luminous fix at Nocturnal (lighting up a beautiful prehistoric valley in the Blue Mountains until May 11).

This month, we’ll also be spending our days stocking up on local goods at the best markets in the city, walking it out on one of these beautiful scenic trails in the city, and warming up with a Sunday roast as winter sets in.

May the force be with us.

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.

Want to get away? These are the best weekend breaks near Sydney, these are the best winter getaways in NSW, and these the best hot springs in the state.

The best things in May

  • Musicals
  • Darling Harbour
  • 3 out of 5 stars
  • Recommended
If you’re of a certain age, you have history (HIStory, perhaps?) with Michael Jackson. I remember getting ‘Thriller’ on cassette as a kid. ‘Dangerous’ was one of the first CDs I ever owned. I remember seeing the extended music video for ‘Thriller’ on VHS, which came packaged with a behind-the-scenes documentary. One woman, cornered for a quick vox pop at one of the filming locations, asserted that she loved Jackson because he was “down to earth”, which is darkly hilarious in hindsight.  Down to earth? The press called him “wacko Jacko” – we all did. He slept in a hyperbaric chamber. He owned the Elephant Man’s skeleton. His skin kept getting paler, his nose thinner. What a weird guy! Was any of it true? Hard to say. Even today, when a careless tweet is like a drop of blood in a shark tank to fans and journos alike, the media furor around Michael Jackson stands as one of the most frenetic in living memory, eclipsing the likes of Beatlemania. Jackson wasn’t bigger than God, he was God to a lot of people – the King of Pop, the first Black artist to smash through the MTV colour barrier, an artist, an icon, a living legend. Then came the allegations of child sexual abuse, which first began in August 1993, and continue to this day. For those who were still on the fence, the documentary Leaving Neverland, released in 2019, saw many more fans abandon Jackson, who died in 2009 at the age of 50. And so, it makes sense that MJ the Musical would set Jackson’s relationship with the...
  • Things to do
  • Exhibitions
  • Dawes Point
It has been more than a century since the Titanic sank into the icy depths of the North Atlantic Ocean, claiming the lives of 1,496 people, and the legend continues to captivate us.  Sydneysiders can explore detailed life-size recreations of the ship’s interiors and take a deep dive into the stories of the people on board at Titanic. The Human Story, open from May 30 at the historic Pier 2/3 in the Walsh Bay Arts Precinct. Created by award-winning exhibitions producer Musealia alongside one of the world’s foremost experts on the Titanic, renound Swedish historian and author Claes-Göran Wetterholm, the exhibition features a selection of around 200 never-before-seen objects and personal artefacts that unveil touching human stories of the ship’s passengers and crew. Far more than just a display of historic items, this is a unique narrative experience, sharing tales from history’s most legendary ship and its ill-fated maiden (and final) journey. The experience encourages guests to travel back in time through photographs, handwritten letters, cherished keepsakes, and other personal belongings. Having captivated audiences with previous iterations across America and the UK, this exhibition welcomed more than 146,000 visitors during its Australian debut in Brisbane in 2024. (Not to be confused with the similarly immersive Titanic: The Artefact Exhibition in Melbourne.) Tip: you'll want to allow about an hour and a half to explore the exhibiton, and you can book ahead for sessions...
Advertising
  • Circuses
  • Darling Harbour
It’s time to ring that bell and check in for an intoxicating blend of Parisian cabaret, dazzling aerial artistry and breathtaking burlesque. Following sold-out seasons at the Sydney Opera House and the Adelaide Cabaret Festival, L’Hôtel returns to Sydney this winter, taking over the brand new Foundry Theatre from May 24 to July 6. Sydney’s own enfant terrible prince of pop Brendan Maclean takes centre stage, causing mischief alongside acting legend John Waters (Offspring, All Saints, Bloom) as L’Hôtel’s devoted hotelier, as well as a jaw-dropping cast of multi-talented entertainers.  The creation of visionary director Craig Ilott (Gatsby at the Green Light, Amadeus) and designer Stuart Couzens, this fresh twist on L’Hôtel promises to be more extravagant than ever. The pair describe the show as a world where temptation lurks in every shadow: “L’Hôtel is where elegance meets mischief, where stolen glances turn into whispered confessions, and every doorway leads to desire. It’s transportative, intoxicating, and unlike anything else in Sydney right now. Prepare to check in.” More than a show, L’Hôtel is a feast for the senses. If you choose to level up to the VIP experience, the night begins with a chilled glass of French Champagne, paired with a curated cheese board featuring the finest French selections. As the drama unfolds, guests will savour delicate éclairs and enjoy dedicated table service – fully immersing them in the seductive world of L’Hôtel from the best seats in...
  • Art
  • Galleries
  • Sydney
  • Recommended
Australia’s most popular arts event is back in action for 2025, with the Archibald, Wynne and Sulman Prizes bringing a fresh batch of painterly expressions to the walls of the Art Gallery of NSW from May 10 to August 17.  They call it “the face that stops the nation”, and the Archibald Prize has indeed been courting controversy and conversation for more than a century now. This popular portrait prize is always filled with famous faces, with artists from all over Australia (and also New Zealand) capturing the spirit of the times through paintings that capture the likeness of the personalities that define their communities. Julie Fragar is the winner of the 2025 Archibald Prize – she won over the judges with a stunning portrait of fellow artist Justene Williams (read more). RECOMMENDED: A beginner's guide to the Archibald Prize. The winner of the 2025 Packing Room Prize was announced a week earlier, with the Packing Room Pickers (a.k.a. the Art Gallery staff who receive, unpack and hang the entries) selecting Abdul Abdullah's striking painting of fellow finalist Jason Phu as their favourite Archibald portrait this year (read more here). Meanwhile, the Wynne Prize awards the best landscape painting of Australian scenery or figurative sculpture, and the Sulman is awarded to the best genre painting, subject painting or mural project. (Find out more about the 2025 winners over here.) The annual finalists exhibition is a real must-see, with each prize attracting diverse entries...
Advertising
  • Musicals
  • Haymarket
  • 4 out of 5 stars
  • Recommended
Just over a decade since it was last seen in Australia, Annie is back – bursting onto the Capitol Theatre stage filled with optimism, joy, and hope. Director Karen Mortimer revives this quintessential piece of musical theatre with a sentimental production that preserves the charm and flair found in Thomas Meehan’s book. For those living under a rock (mainly me), this Tony Award-winning musical follows the story of 11-year-old Annie, who is growing up in an orphanage in 1930s New York, under the cruel eye of Miss Hannigan. In the midst of the Great Depression, pessimism is all around, but chipper young Annie has the antidote: hope. Encouraging others to believe that “the sun will come out tomorrow”, Annie’s enduringly positive spirit seems to finally pay off, when billionaire Oliver Warbucks chooses to take her in for two weeks over Christmas. Four spirited young performers share the titular role in this production, alongside an alternating cast of child actors. On opening night, Dakota Chanel’s Annie is a ray of sunshine, fully embodying the doe-eyed optimism of the character, balancing warmth and comedy with the more tender and emotional segments. The whole ensemble of “orphans” share an incredible chemistry, which is strongly on display in their performance of ‘It’s The Hard Knock Life’. The stakes are high when it comes to such a well-known and well-loved song, but this ensemble more than meets the challenge with a passionate and committed performance.  Annie is the...
  • Art
  • Sculpture and installations
  • Waterloo
You know you’re adulting when you find joy in browsing through homewares and furniture stores. Supa Centa Moore Park is like a massive playground for adults and it’s just been made even more of a great day out thanks to an immersive sculpture trail throughout the centre's public spaces.  This autumn, more than 25 contemporary sculptures crafted by renowned Australian artists will be arranged throughout the space in the Supa Sculpted Moments exhibition. The free, public collection includes work from artists Stephen Glassborow, Sonia Payes, Michael Vaynman, Margaret Sheridan, Mela Cooke and Hugh McLachlan, whose works have been displayed in some of Australia’s best galleries and prestigious exhibitions like Sculpture by the Sea.  There’s even an opportunity to get the scoop from the artists themselves, with a Meet the Makers series. For $10 (which includes a coupon for The Depot Cafe – so it’s basically free, right?) you can snag a limited spot for insight on the creative process (hello, home decor inspo).  Like what you see? Tell Supa Centa Moore Park which work is your favourite and you’ll go in the running to win a $2,500 art curation package including a discovery session, site inspection with an art curator and digital mock-up of suggested artworks for your home, bringing the spirit of Supa Sculpted Moments into your everyday living spaces. Supa Sculpted Moments is showing at the Supa Centa Moore Park from May 3 to July 20. It’s free to check out. You can find out more...
Paid content
Advertising
  • Shopping
  • Markets
  • Eveleigh
Carriageworks Farmers Market
Carriageworks Farmers Market
It’s imperative that you do not eat before you visit the Carriageworks Farmers Markets. You’ll want to save maximum belly space for your personal version of The Bachelorette where you decide who gets your dollars and what delicious produce gets to come home with you. Maybe you like something soupy and savoury first thing? In that case head to Bar Pho for a traditional Vietnamese start to the day. On the veggie train? Hit up Keppos St Kitchen for a falafel breakfast, or head to Food Farm for a classic bacon and egg roll.Once the hounds of your hunger have been quieted it’s time to prepare for your next meal, or seven. Stock up on artisan cheese from Leaning Oak, smoked salmon from Brilliant Foods and Sydney’s favourite sourdough from AP Bakery and brunch is sorted. You can spend a whole lot of money if you want to here, but equally you could just grab a kombucha on tap from Herbs of Life and find a chair for some of the best dog-watching in the city.  Stay in the loop: sign up for our free Time Out Sydney newsletter for more news, travel tips and city insights, straight to your inbox. Hungry for more? Look at our list of the best markets in Sydney – produce or otherwise. 
  • Musicals
  • Redfern
  • 5 out of 5 stars
  • Recommended
Ah, the Titanic. An unsinkable cultural icon, the “Ship of Dreams” has appeared in almost as many movies and stage productions as the songs of Canada’s queen of the power ballad, Céline Dion. It’s even got a two-and-a-half-hour (surprisingly serious) movie musical adaptation based on Maury Yeston’s Titanic: the Musical. Although, none can hold a candle to the cultural impact of James Cameron’s 1997 blockbuster – you know, the one with Kate Winslet and Leonardo DiCaprio. So, with nostalgia being such hot property right now, it was only a matter of time before we got the camp-as-hell musical fantasia made-for-and-by-the-gays that is Titanique. Created by Marla Mindelle (who originated the role of Céline Dion – well, as imagined in this show), Constantine Rousouli (who originated the role of Jack) and director Tye Blue (whose countless industry credits include working on the casting team of RuPaul’s Drag Race), Titanique is revisionist history at its best. Loaded with Céline Dion’s greatest bangers, it casts Queen Dion herself (played so wonderfully by cabaret legend Marney McQueen here in Aus) as the narrator of the tragic tale, who continuously places herself at the center of the action – quite literally – much to Jack and Rose’s repeated dismay. It brings the campness of the film to the front, with Stephen Anderson (Mary Poppins) playing Rose’s awful mother Ruth (complete with a bird’s nest headpiece), and Abu Kebe (Choirboy) playing a brilliant, tear-jerking drag parody...
Advertising
  • Art
  • Galleries
  • Darling Harbour
If you can’t quite hack the requisite international airfare and/or annual leave to explore the Amazon, meet polar bears, or go deep sea diving right now, there is another method for getting up close and personal with some of the world’s most incredible animals.  For the 60th year in a row, the Wildlife Photographer of the Year exhibition will arrive in Sydney on loan from London’s Natural History Museum. Taking root at the National Maritime Museum, this stunning collection of photographs will be on show in Sydney from Thursday, May 15 until Sunday, October 19.  This incredibly prestigious photography event is centred on drawing attention to the wild beauty and fragility of the natural world. This year, judges had to look at a baffling 59,228 entries from photographers of all ages and experience levels from 117 countries and territories, and were faced with the near-impossible task of whittling these down to just over 100 photo finalists. The images that made this year’s exhibition captures mesmerising snapshots of fascinating animal behaviour and stunning secret moments in the hearts of the world’s most unreachable places.The prestigious Grand Title this year went to Canadian Marine Conservation Photojournalist, Shane Gross, for his incredible underwater image of a community of western toad tadpoles. The award for Young Wildlife Photographer of the Year went to German photographer Alexis Tinker-Tsavalas for his up-close image Life Under Dead Wood. Of the talented Aussie...
Paid content
  • Shopping
  • Markets
  • Paddington
Paddington Markets
Paddington Markets
Every Saturday, more than 100 stalls line the grounds of Paddington Uniting Church and the neighbouring public school selling Australian-made fashion, handmade crockery and metal costume jewellery. The market has been operating on the same day since 1973, and the all-weather event is a profitable fundraiser for the church. Many of the stallholders return week on week, like the elderly Japanese couple selling Bonsai trees and the Spanish shoemakers selling espadrilles. It’s predominantly an art, clothing and design market – and alongside the kitsch bric-à-brac and Australiana-print tea towels you’ll find straw hats from local milliners and soft Tunisian-made ‘Turkish’ towels from young Eastern Suburb entrepreneurs. Antique, vinyl and vintage stalls are few and far between, but leather satchels, beach photography prints and patterned baby rompers are two a penny. On a hot day locals gather at the shaded tables and stools by the snack stalls. Turkish women hand roll yufka dough at the gözleme tent and vegetables are blitzed in a blender at the fresh juice stand. Chin’s Laksa stall, proudly MSG and gluten free, is a popular choice – as are the vegan cookies and sourdough scones on offer at the bakery stalls. It has a bohemian flair compared to its Oxford Street location and customers joyfully take up fortune readings, as well as reiki and Japanese massage. It’s an oddball mix, but one that works strangely well in an area known for its designer boutiques and gentrified pubs....
Recommended
    You may also like
    You may also like
    Advertising