September's biggest events
It’s free to enter this popular harbourside festival, which is now in its ninth year. Sample a few cool-climate vintages, mingle with winemakers, listen to live music and explore more than 100 stalls of regional produce at Pirrama Park.
Sydney's Fringe might not be as old or well-funded as Melbourne's, but it's spreading its footprint much further for its tenth anniversary. While the festival has its traditional hubs of music, theatre, art and performance across the Inner West, it's also taking over the CBD this time around.
Showcasing the latest video games, anime, sci-fi and fantasy stories, the weekend will be a pop-culture hub where attendees can get creative with cosplay and browse exclusive merchandise. Meet stars like the leading lady of the Marvel Cinematic Universe Hayley Atwell, and Rick and Morty contributor Dean Rankine.
Brisbane performers and real-life friends Natalie Bochenski and Amy Currie aren't afraid to ask the tough questions. Namely: is Love Actually a perfect rom-com or does it suck, actually? Amy will advocate for the Christmassy flick while Natalie dismisses the movie as an outdated and awkwardly constructed piece of fluff.
Hop on your bike and explore Mrs Macquarie’s Point at this free, family-friendly bike ride. Riders are encouraged to get glowed-up and enjoy sunset harbour views around the point, the disco dancefloor and glowing art installations.
Why is it that we know so much about NZ’s prime minister Jacinda Ardern and her partner Clarke Gayford’s parenting decisions, but we know so little about Scott Morrison’s? Annabel Crabb is deploying her astute political observation to the ongoing inequality around the social expectations of fatherhood.
If you think you know more about swordplay than John Snow or if your skills with a lance are far superior than William Thatcher’s, head to St Ives Medieval Faire. The ye olde celebration goes back into the Dark Ages and the bloody centuries that followed for a weekend of jousting, feasting and medieval merriment.
Sydney Fringe likes to open with a bit of a bang: a free musician-curated street festival called 'Fringe Ignite'. It's heading back to Newtown, where Fringe was born ten years ago, and joining King Street Crawl to pack every available space on King Street with live music.
Literal angel Troye Sivan is coming to Sydney this month. It will be the first time Sivan has toured on home soil since 2016 and fans will no doubt be frothing to hear hits like ‘My My My!’, ‘Dance to This’ and ‘Bloom’ at the musician’s high-energy show.
A music and arts festival unlike any other in Sydney, Soft Centre whirrs, flashes and throbs through the cement-bound hallows of the Casula Powerhouse. This year the festival is curated by the hot shots behind Dark Mofo's insanely popular Dark Mass, so you know you are in good hands.
Central Coast comedian Celeste Barber is known for her self-deprecating and rib-snortingly funny Instagram influencer parodies. It’s the Challenge Accepted series that Barber has morphed into a stand-up comedy show, which she’s touring around the world – and now bringing home to Sydney.
Packed full of corruption, rape, cannibalism, mutilation and murder, Titus Andronicus is generally considered to be Shakespeare’s most violent play and tells the tale of two families locked in a cycle of bloodthirsty vengeance during the Roman Empire.
Join this fair-weathered outdoor shopping excursion hosted by market masters, the Cambridge Markets. They’re setting up their regular contingent of local, artisanal stalls in Robertson Park on the bay foreshore, offering everything from high-end womenswear to children’s toys, jewellery, art and homewares.
The Big Anxiety is returning to shine a light on mental health. It’s being organised by UNSW in collaboration with the Black Dog Institute and other mental health awareness organisations and practitioners to bring a series of conferences, workshops, exhibitions, performances and interactive experiences to Sydney.
Is it inevitable that somewhere down the line we'll start to see romantic relationships between humans and robots? Of course, sex robots already exist, but what about something deeper? That's one of the questions that's at the core of this comedy (a one-woman, two-hander) from Irish Theatre Company Malaprop.
They’re mixing old-fashioned community fair vibes – think tea cup rides, roller skating, face painting and acrobats – with light shows and after dark fun. There’ll be dancers lit up by LED bulbs, hula hoop performers, fire twirlers, luminescent fairy floss, giant glowing flowers and inflatable mushrooms.
If this bus drops below 50 miles per hour (about 80km/h) we all die. That's the premise of Speed, the 1994 Keanu Reeves and Sandra Bullock action thriller. But what happens when you take the show out of the cinema and put it inside (and around) a vintage Volvo for a theatrical adaptation?
This year Sydney Fringe is turning its focus to the CBD and making the 120-year-old City Tattersalls Club one of its main hubs. And to help City Tatts feel young again, party people Heaps Gay are taking over the venue for one night of wild debauchery.
Before The Sapphires became a hit film, it was a hugely popular play, telling the story of a group of Yorta Yorta women who travel to Vietnam in 1968 to perform soul classics for the troops. Tony Briggs based the story on the real-life experiences of his mother, and he's returning to direct this new production.
Forks at the ready, Sydney: the Time Out Food Awards are returning. Time Out readers will join the stars of the local restaurant industry to celebrate the city’s best restaurants, cafés and chefs.
The musical was only a minor splash when it premiered in 1975, but when it was given a stripped back and sexed up production in 1996, it became a sensation and eventually the longest running Broadway revival of all time. That's the production which Sydney audiences will see.
The Blackmores Sydney Running Festival has distances to suit all runners – from a family-friendly 3.5k to a leg-wobbling 42.2k. Starting at Milsons Point, the courses offer some of the most scenic routes in Sydney, with each distance crossing the Harbour Bridge.
The Lips are bringing their elaborate, technicolour party to the Opera House for two nights in September and October. They’ll be performing their breakthrough album The Soft Bulletin, channelling all their weirdness into their signature wild stage presence – including props, costumes and confetti cannons.
British author, scientist and physician Michael Mosley is returning to Sydney to reveal secrets about the human body. In this talk, he will share his insights about living a healthy lifestyle at all ages, and footage from his escapades captured while uncovering his ideas.
Cambridge Analytica whistleblower Chris Wylie, Sonic Youth co-founder Kim Gordon, and Black Lives Matter activist DeRay Mckesson are all speaking at the next Antidote – a festival of ideas, action and change. This year’s festival will include solo talks, panels and workshops that respond to our world today.
This show brings together award-winning performer Sandy Greenwood's experiences as a fair-skin Indigenous woman with the stories of four generations of Gumbaynggirr women. Using story, dance, music, traditional language and multimedia, Greenwood is exploring the intergenerational impact of the stolen generation.
This new party on wheels ticks off just about every Sydney-day-out ideal: harbour views, bottomless booze and a retro theme. They’ll be pumping tracks from the ’80s while you zoom around the arena on the rooftop of Cruise Bar in Circular Quay.
This bike-riding bonanza will give you that extra push to get back on the pedals this spring, with more than 40 bike-based events happening across the city, including cycling courses and family-friendly food, art and sporting events.
Full disclaimer: Bill Bryson is not an actual scientist with any kind of professional expertise in human anatomy, but he is an author with a knack for explaining the more complicated things in life with a laugh. Bryson will unravel his investigation into the human body in a live talk with Julia Zemiro.
Kate Miller-Heidke is absolutely dominating our musical worlds right now, from international competitions to hilarious musical theatre. Now, as part of a one-off special performance during her national tour, Kate Miller-Heidke will be performing ‘Zero Gravity’ at the Sydney Opera House.
When you're a teenage boy, just about the last thing you want to do is make and perform a show with your mum. But that's exactly what Raedie Gaizely-Gardiner did with his mum Lucy when he was just 14, with Australian singer Sia as its core.
Aeschylus’ classic Greek tragedy has been transplanted to Sydney and given a distinctly Australian reworking by Ang Collins at the Old Fitz. Agamemnon is a pop star just returned home from a global concert tour to deal with some unfinished business and start her life afresh.
Whether you were enamoured with the sexy-scary story of Twilight, or completely despise the 2008 film and subsequent saga, you’ve got to admit a screening at the Opera House with a full symphony orchestra would be quite a sight to see (and hear).
Artisans Market Glebe is all about handmade and local products, sold direct to you by the artist or designer who created them. The quarterly market takes place at Foley Park and there are around 60 stallholders selling jewellery, plants, furniture, fashion and children's toys.
Geraldine Hakewill and Toby Schmitz will star in this Tom Stoppard play about the nature of real love. Of course, being Tom Stoppard, things aren’t entirely what they seem and there’s a play-within-a-play device happening. But it still ranks as one of his most charming and human stories.
The Manly Fun Run is turning ten in 2019, and amblers of all abilities are invited to celebrate the double digits with 2km, 5km and 10km races. They’ve updated the courses this year, which will start and finish at Hotel Steyne.
While you won’t find the most famed greasy-haired potions masters or boy wizard at this creative drinking experience, you will have a lot of fun if you’re keen on the occult. Channel the powers of your coven idol and brew devilish concoctions in your cauldron.