May – always a spectacular month for live events in Sydney. Look it's no January, but for a soggy autumn month with short days and zero public holidays, it holds its own.  

The city hosts Sydney Comedy Festival, Sydney Writers' Festival, the beaming cultural behemoth that is Vivid Sydney, National Reconciliation Week, plus plenty more live music, theatre, art fairs and cultural gatherings. 

No more time for full sentences with all this live performance to get to. We’re switching to list format for this What’s On. 

First Nations highlights 

22 May – Past and Future of Indigenous Recognition, talk with Thomas Mayo and Clare Wright, at Carriageworks (Sydney Writers’ Festival) 

22–27 May  – Ngana Birrung (Dharug for Black Stars), First Nations music events in Parramatta, Penrith and Campbeltown

23 May – First Light Live, featuring Rona, Akala Newman and more, at Campbell’s Cove (Vivid Sydney)

24 May – Afloat: Storytime with Kirli Saunders – childrens’ event at Parramatta Library (Sydney Writers’ Festival) 

24 May – Emily Wurrumara, live music at Sydney Opera House Utzon Room (Vivid Sydney) 

26 May – National Sorry Day, gatherings across the country including at Parramatta Square, Blacktown City Festival and Royal Botanic Gardens in the CBD.  

27 May–3 June – National Reconciliation Week, varied events across the country 

28 May – 3%, live music at Sydney Opera House Utzon Room (Vivid Sydney) 

29 May – Sing with Barayagal Choir, community event at Green Square Library. 

29 May – Velvet Trip, live music at Sydney Opera House Utzon Room (Vivid Sydney) 

29 May – Sea Gathering, family-friendly light show, live music and activities, at Australian National Maritime Museum (Vivid Sydney) 

30 May – Miss Kaninna, live music at Sydney Opera House Drama Theatre (Vivid Sydney) 

3 Jun – Native Food Experience, First Nations fine dining at NSW Parliament House (Vivid Sydney) 

Vivid Sydney highlights 

23 May–14 Jun – Neon Dreams, Roller disco and vegan food fair, at Tumbalong Boulevard 

23–25 May – Sigur Ros with Sydney Symphony Orchestra, at Sydney Opera House Concert Hall 

24 May – PASIFIX | Tumbalong Nights, free event celebrating Pacific Islander music and dance, at Tumbalong Park 

25 May – Studio Party by House of Mince, featuring Berlin DJ Boris, at Sydney Opera House Studio 

26–27 May – ANOHNI and the Johnsons, at Sydney Opera House Concert Hall 

27 May – Why We Sleep, talk with Professor Matthew Walker 27 may, at Sydney Town Hall (presented with Sydney Writers’ Festival) 

29 May – Where Do Ideas Come From? Creativity inside TIME’s Cover, at Sydney Town Hall 

28 May – In Conversation with Martha Stewart and Benjamin Law, at ICC Sydney Theatre

28 May – Jessica Pratt, at Sydney Opera House Joan Sutherland Theatre 

29 May – Marlon Williams, at Sydney Opera House Concert Hall  

29 May–12 June – Inside the Dream Factory (I Don’t Dream, I Float), immersive soundscape, at Sydney Theatre Company 

31 May – Studio Party by Mad Racket, featuring UK DJ Red Rackem, at Sydney Opera House Studio  

31 May – Ezra Collective, at Sydney Opera House Concert Hall 

Sydney Writers’ Festival highlights 

21 May – The Art and Science of AI, with Jeanette Winterson and Toby Walsh at Carriageworks

21 May – Queer Love and Longing, with Dylin Hardcastle Alan Hollinghurst and Yael Van der Wouden, at Carriageworks 

22 May: SWF Great Debate: True Friends Stab You in the Front, with David Marr, Annabel Crabb and more, at Sydney Town Hall

22 May – Markus Zusak: Three Wild Dogs and the Truth, with Richard Glover, at Carriageworks

22 May – Jeanette Winterson: 40 Years of Oranges are Not The Only Fruit, at Sydney Town Hall 

23 May – Bankstown Poetry Slam, with Plestia Alaqad, at Sydney Town Hall 

23 May – Samantha Harvey: Orbital, at Sydney Town Hall

23 May – The Power of Choice, with Andrew Denton and more, at Carriageworks

24 May – A.C. Grayling on Cancel Culture, at Carriageworks

25 May – Making A Writer, with Colm Toibin, at Carriageworks  

Sydney Comedy Festival highlights

1–4 May – Akmal, at The Foundry 

2–11 May – An Evening Without Kate Bush, multiple locations

3–4 May – Aditya Gautam: Unskilled Immigrant, at Enmore Theatre

7–11 May – Ruby Teys – Cheryl Vinyl: Coober Pedy's Last Showgirl, Factory Theatre

10 May – Ashwin Singh: The Audacity, Enmore Theatre

15–18 May – Chris Ryan: Extreme Tenant, Enmore Theatre

16–17 May – Arj Barker: The Mind Field, multiple locations

Highlights from beyond the festivals

Until 3 May – The Princess, the Pea and the Great Escapee with Australian Chamber Orchestra, at Riverside Theatres

2–4 May – The Finders Keepers Design Market, at Carriageworks

8–11 May – The Other Art Fair, at White Bay Cruise Terminal 

Until 11 May – Bloom by Sydney Theatre Company, at Roslyn Packer Theatre

10–14 May – Theramin & Beyond with ACO, multiple venues

16 May – Skeleten (live) with Shady Nasty and more, at Liberty Hall

16 May – Ewan McVicar (DJ set), at The Roundhouse

16–17 May – Ruel with Ensemble Apex, at Sydney Town Hall 

Until 17 May – RBG: Of Many, One by Sydney Theatre Company, at Sydney Opera House Drama Theatre