Your Autumn to Winter Sydney Staycay Guide

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Drumroll, please! Say hello to your ultimate Sydney events guide. The sunny city may be known for its sun-soaked summers, BUT, we’re here to tell you there’s just as much to do as it chills down. It’s time to prepare your eyes, ears and palates for some of the biggest festivities of the year. From mouth-watering food to the silver screen and the comedy stage, over to iconic harbour-side light shows and musical epiphanies — we’ve got you covered. Mark your calendars folks, these events are THE events to add to your calendar. Let’s get into it:


Vivid Sydney 2023

Where: Sydney-Wide — for the light show, head to the Harbour.

When: May 26 – June 17th

Lights, camera, action! Sydney’s most iconic winter festival is back and bigger than ever, with a stunning display of lights, music, and art set to transform the city for 23 days and nights. There’ll be talks, performances and landmarks (the Opera House!) dressed to the nines in spectacular, digitised fashion. Feat. boundary-pushing works from some of the most innovative artists, thinkers, and musicians of our time. Stunning visuals, guaranteed. A highlight? Miss Comedy Queen, Jennifer Coolidge is landing down under to grace the Vivid stage on June 10th. Don’t. Miss. It. 


The National 4: 

Where: Across the Art Gallery of New South Wales, Campbelltown Arts Centre, Carriageworks, and the Museum of Contemporary Art Australia

When: Until June 25th

Calling all art lovers! Here lies a biennial survey of contemporary Australian art, bringing together 48 new artist projects from over 80 artists across the country, generations, and communities. Head here for the ins and outs of Australia’s art scene.


‘Unpopular’ Exhibition:

Where: the Powerhouse Museum, Ultimo

When: Until June 4th

Music fiends, gather round. This exhibition takes you behind-the-scenes of the alternative music scene circa 1990s, drawing on the never-before-seen archive of music promoter, record company founder, and entrepreneur Stephen ‘Pav’ Pavlovic (humble brag: he’s the guy who brought Nirvana to Australia for the first time) A must-see before it wraps in June for all you Sonic Youth, Beastie Boys, Nirvana, Bikini Kill, Fugazi or Pavement fans. 


Semi Permanent Creativity and Design Festival: 

Where: Carriageworks, Redfern

When: May 31 – June 2nd

For the creatively inclined. Semi P returns to Carriageworks as part of Vivid Sydney 2023, bringing together leading designers, artists and industry revolutionaries from across the Asia Pacific. Over three full days of innovative talks, panel discussions, workshops, exhibitions and installations, you’re guaranteed to leave with a new, future-forward perspective.


Sydney Writers Festival: 

Where: Carriageworks, Redfern                                                                                                               

When: May 22 – May 28 

Bookworms, unite! This is surely Australia’s most beloved celebration of writing and ideas. With authors, thinkers, and readers all coming together to share ideas, tell stories and, well, celebrate all things LITERATURE. Bookmark this one, there’s tales to tell. 


Sydney Comedy Festival

Where: From the pub to the more glam stage. Head to their website for ticket details.

When: April 20 — May 21st

*Queue the laffs* for one of the largest comedy festivals in the world, feat. local and international comedians performing stand-up, sketch comedy, and improv galore. If life’s got you stiff, head here to loosen up.


Sydney Film Festival

Where: Cinema-wide, head to their website for showtimes.

When: June 7 – June 18th

Prepare your ears, eyes and hearts movie buffs! Presenting one of Australia’s largest and most prestigious film festivals, showcasing a diverse range of films from around the world. From acclaimed features to indie flicks, there’s something for everyone. Grab your popcorn and settle in for a week of silver screen seduction.


Winterlight Festival:

Where: City-wide. Head to the website for the full guide.

When: June 10 – July 9th

 Embrace the ch* ch* chill with this timely celebration of all things ‘ice, ice baby’. From ice-skating to winter markets and tummy-warming street food, the festival offers a range of activities for all ages. Well worth venturing out of the inner city for. So! Rug up, get snug and come play. Who said Sydney couldn’t do winter?!


Sydney Biennale

Where: From AGNSW to the MCA to smaller, locally run galleries. See website for details.

When: Until June 5th

Australia’s largest contemporary art event, featuring works from local and international artists. Explore installations, sculptures, and multimedia works at various venues across Sydney.



Where: City-wide

When: July 3 – July 10th

Join us in celebrating the history, culture, and achievements of Aboriginal and Torres Strait Islander peoples. Feat. must-see cultural performances, art exhibitions, live music, dance, native ingredients and workshops galore.


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