Things to do in Sydney in May

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...

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.  Local distillery Hickson House Distilling Co will be slinging gin-based cocktails, and there are a host of excellent restaurants in the area to keep you nourished pre and post show. 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

Call it “One Flew Over the Old Bird’s Nest”, if you like. Following its hugely successful debut with Melbourne Theatre Company in 2023, veteran comedian and Working Dog mainstay Tom Gleisner’s (The Castle, ABC television's Utopia) catchy new musical comedy set in a nursing home (and seasoned with a dash of tears, as expected) is now Sydney Theatre Company’s latest and very welcome offering. Directed by Dean Bryant (Dear Evan Hansen) with music by Katie Weston, Bloom is an across-the-board crowd-pleaser, the kind of popular four-quadrant gem that’s almost impossible to dislike. It even has a few pointed comments to make about the fraught state of aged care in Australia, but these never overwhelm the palpable sense of fun. What more could you want? We get two fish out of water (or Randle McMurphys, if you will) for the price of one here, both arriving at the understaffed, underfunded (and, as it eventuates, underestimated) Pine Grove Aged Care facility on the same day. One is new resident (or possibly inmate?) Rose (played by Evelyn Krape, reprising her role from the Melbourne run) – a feisty-to-the-point-of-prickly old dame, age has not wearied Rose, but it did lead to an accidental fire that made her an unwilling candidate for permanent care. The other is stoner/slacker/music student Finn (Sloan Sudiro), who was drawn here by the promise of a free room and board in exchange for some light duties. The duties turn out to be anything but light, as the frazzled staff –...

Real ale fanatic? Craft brew aficionado? We’ve got news. The GABS Beer Festival – the most anticipated event on Australia’s beer calendar – is heading back to Sydney this May. Complete with a 30-metre bar (the longest in Australia) GABS will bring more than 500 brews to the Harbour City for festival goers to have a crack at. Attendees of GABS25 can head along to the International Convention Centre to sample the extensive selection of daring, out-of-the-box concoctions. Among the line-up of funky frothies will be some seriously unique tipples like the Broken Bay Pearl Beer from Six String Brewing Co in Erina that was made using 1000 shucked oysters. If you’re not saying “what a pearler” two pints in, that’s on you. Elsewhere on offer you can get your laughing gear around the Gingerbread Pastry Beer (yes) from Shout Brewing Co in Newcastle or the Pickle Beer (double yes!) from Stoic Brewing in Gerringong.  The creativity of these breweries knows no bounds, with the likes of The Socials Brewers in Mortdale heading to GABS25 to show off their Vegemite, stale bread and Indigenous macadamia nuts beer. Sounds yeasty. For the sweet toothed among us, there’s a Rainbow Ice Cream Cone beer by Good Land Brewing which is stacked full of strawberries, bananas, cherries, blueberries, vanilla ice cream and bubblegum.  There will also be some European guest breweries at the festival including the world’s oldest brewery, Weihenstephan, all the way from Germany. With 500+ beer taps on offer,...

To the common eye, the scene laid out in the Old Fitz Theatre (designed by Soham Apte) may appear lavish: a long oak table prepared for a feast; walls of wooden panelling and patterned green wallpaper; gilded portraits of dead aristocrats; an icy chandelier glittering above it all. But to the Oxford boys of the Riot Club, this private dining room of a regional gastro pub is a humiliating exile. Not only that – staffed by a father and daughter who aren’t educated in the natural, money-greased rules of subordination to their ‘betters’ – it’s an existential threat. The ten members of this exclusive club were banished here, on the outskirts of London, to host their next dinner (a quarterly custom) after one of them breached the strict pact of absolute secrecy. Once open and proud, their bizarre rituals of excess must now keep to the shadows. Gone are the days of legendary mayhem and glorious carnage without consequence; when their promised inheritance of seats of national power was iron-clad. (Or are they?)  As entertaining as it is savage... A dark comedy turned social horror over two acts penned by UK playwright Laura Wade in 2014, Posh is a study into how the “good old boys” have survived society’s staggered lunges towards equality over the last century. Inspired by real-life events, we see two generations conspiring to uphold the obscene traditions of class entitlement, patriarchal privilege, and their cashed-up “right” to do whatever they want. Director Margaret Thanos...

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...

  So, who else could use a laugh? Good news for us, the Sydney Comedy Festival is gearing up to celebrate its 20th anniversary with its biggest program ever in 2025 (from April 21 to May 18). With brand-new experiences and more than 350 acts from near and far to get around, it’s time for you to prepare yourself for some next-level laughs and silly shenanigans. We’re particularly keen on the brand-new Sydney Comedy Festival Comedy Crawl that will come to life amongst the top-notch bars in the YCK Laneways precinct in the CBD. Led by a host, you can join a group of punters and take a chance on a surprise line-up in surprise venues, moving from bar-to-bar for each comedy set. The Festival’s inaugural ‘One Night Stand’ will also bring Daniel Sloss to town (with some friends) for an Australian exclusive performance at the Sydney Opera House for one night only on April 24, marking the beginning of annual Sydney-only shows. (That’s right, he’s not even going to MICF this year!) Sloss joins a colossal list of big names appearing in the Festival, including Aussie comedy legend Rhys Nicholson (Drag Race Down Under), Guy Montgomery, Jimeoin, Arj Barker, Melanie Bracewell, Nazeem Hussain, Becky Lucas, Joel Creasey, Rhys Darby and Steph Broadbridge – whose brand new Raygun-inspired show Breaking the Musical has already made quite a bit of noise.  You can find also check out our list of 14 top shows to see at Sydney Comedy Festival in 2025 for more inspo.   Another Festival first is...

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. 

A neat little parcel enclosed in a perfect pink box from Pandora is already a fabulous enough gift for your nearest and dearest women, but this Mother’s Day, you can get a piece of jewellery engraved and wrapped up extra nice so it’s even more meaningful. For a limited time, the flagship David Jones on Elizabeth Street is hosting a Pandora pop-up where you can get your piece of jewellery engraved with initials, special messages and even sentimental drawings just in time for Mother’s Day. Getting a special person in your life a personalised (and very thoughtful, may we add) gift can start from as little as $50. Purchase a delicate item from the Pandora engravable range at David Jones and you can get it engraved for free on the spot. Take a browse of engravable pieces, including everything from bracelet charms and necklace pendants to signet rings.  Just make your way to the top of the David Jones elevators and you’ll find the station set up on level one. Don’t leave this one ’til late – the pop-up is open now for a limited time. You can find out more about the pop-up here.

April 27, 2025 update: Transcend by Penfolds will also included a dedicated pop-up Bar, the Penfolds Lounge, open to walk ins and serving a range of wines by the glass.  Forget everything you’ve ever known about a normal, run-of-the-mill wine tasting session, because this exclusive 45-minute, multi-sensory experience is set to change the game. Transcend by Penfolds is a wine tasting reimagined, and offers the opportunity to sample Penfolds wines made in some of the best winemaking regions around the world, including Australia, France and the USA – as well as a taste of Penfolds' flagship Grange.  But that’s not all – everything about this highly immersive spectacle has been designed to enhance your sensory experience. Expect a unique soundscape accompanied by storytelling elements, plus dazzling visuals and lighting. The guided tasting will also be narrated by Penfolds senior winemaker, Steph Dutton. The experience will hit its crescendo with a ‘Grange palate cleanser’, which has been specifically designed to reinvigorate the palate ahead of tasting the Penfolds Flagship, Grange. It will leave you well and truly prepped to enjoy the gamut of complex aromas and flavours that Grange is most famous for. It’s all happening from May 2-11 in Sydney Arcade at 400 George Street, with multiple sessions available per day. To ensure you don’t miss out on this opportunity to try some really special tipples and throw around some fancy wine words, book your spot via the website.