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The best events in May

There's a glowing line-up of festivals and events to explore this month
MCA Sculpture Terrace outdoors music
Photograph: Sam Whiteside
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Put on your thinking caps and practice your belly laughs for this huge month of intrigue and chilly adventures. While April saw the opening nights of the Sydney Writers’ Festival and Sydney Comedy Festival, there’s more on the way in May, plus the glittering beginning of Vivid Sydney.

When you’re not all cosied up inside well-heated theatres, hit the unpaved roads on some of the best walks in Sydney. Don’t forget to bring your binoculars, as it’s also the start of whale-watching season. And double don't forget it's Mother's Day this month, too.

RECOMMENDED: Food and drink festival in Sydney.

The best things to do in May

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Theatre

Puffs, or: Seven Increasingly Eventful Years at a Certain School of Magic and Magic

icon-location-pin The Entertainment Quarter, Moore Park
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The universe of Harry Potter truly is a magical place. Unless you spend a few seconds really thinking about it. The kids are armed at 11, there’s mass slavery, rampant racism and a huge class divide. Puffs takes every plot hole to task with a hilariously enchanting mix of parody and homage.  

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People clapping at a Sydney Writers' Festival talk
Photograph: Prudence Upton
Things to do, Talks and discussions

Lie to Me: An Evening of Storytelling at Sydney Town Hall

icon-location-pin Sydney Town Hall, Sydney
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Keeping in mind the Sydney Writers' Festival theme, 'Lie to me', Benjamin Law will be wrangling questions and answers, stories and songs, from Oyinkan Braithwaite (My Sister, the Serial Killer), former Greens senator Scott Ludlam, playwright Patricia Cornelius, writers Nayuka Gorrie and Ece Temelkuran, political theorist Tim Soutphommasane, and musician Megan Washington.

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Alice in Slasherland Old Fitz Theatre 2019 image supplied
Photograph: Supplied
Theatre, Drama

Alice in Slasherland

icon-location-pin Old Fitzroy Theatre, Wooloomooloo
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Meet Lewis, whose love for his best friend has opened a literal portal to hell and resurrected the soul of a brutally slain girl called Alice. With demons on their trail, it’s up to Lewis, Alice and her trash-talking demonic teddy bear to save the town before senior prom is ruined. 

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Three women on a panel about podcasts
Photograph: Bryce Thomas
Things to do, Fairs and festivals

Audiocraft Podcast Festival

icon-location-pin Multiple venues
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Whatever podcast topics you fill your ears with, there’s bound to be a speaker or event that pricks those little listeners at Audiocraft Podcast Festival. They’ve lined some of the best in the audio game to lead masterclasses, panel discussions, workshops, guided listening experiences, and live podcast recordings across three locations over the three-day festival. 

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Vivid sydney 2018
Photograph: Daniel Boud
Things to do, Fairs and festivals

Vivid Sydney

icon-location-pin Around Sydney, Sydney
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The world’s largest festival of light, music and ideas is now in its 11th year. Last year, the annual winter festival received 2.25 million visitors to the city for free illuminations from 6pm every night, plus headline music acts and talks and workshops to stretch those mind muscles.

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Photograph: Steffen Pedersen
Things to do, Food and drink

Mould: A Cheese Festival

icon-location-pin Carriageworks, Eveleigh
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Mould: A Cheese Festival is exactly what it says on the tin – a joyous celebration of handmade Australian cheeses. Over two days, you’ll be meeting a more than 60 members of the cheese family, from tart blue veined varieties to crumbling aged cheddars, washed rind numbers and super smooth soft rounds.

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Woman shopping at MCA Zine Fair 2016
Photograph: Jacquie Manning
Things to do, Exhibitions

MCA Zine Fair

icon-location-pin Museum of Contemporary Art (MCA), The Rocks
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The MCA will become a marketplace of independent self-published zines exploring visual arts, poetry, politics, fanfiction and personal experiences. Meet the makers behind niche reads, hear from creatives and industry professionals and fill your minds with new stories and ideas at the free event on the MCA lawn.

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Rhys Nicholson Nice People Nice Things Nice Situations 2019
Photograph: Supplied
Comedy, Stand Up

Rhys Nicholson: Nice People Nice Things Nice Situations

icon-location-pin The Enmore Theatre, Newtown
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When we saw Rhys Nicholson’s last stand-up show, we said: “Most comedians would kill to hear the almost unending screams of laughter Nicholson manages to extract from a crowd.” We're looking forward to seeing what subjects he’ll wrap his sharp tongue and lightning-fast acerbic wit around in May.

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Alma Har'el portrait.
Photograph: Supplied
Things to do, Talks and discussions

Semi Permanent

icon-location-pin Carriageworks, Eveleigh
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The three-day design summit Semi Permanent has announced its 17th annual series of talks, workshops, exhibitions, screenings and parties. Anchored on a theme truth, Semi Permanent will investigate how designers can shape and support the creative and economic future they believe in. 

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Things to do

The Million Paws Walk

icon-location-pin Sydney Olympic Park, Sydney Olympic Park
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Sydney’s good boys and girls will be stepping it out in a floof pack for the Million Paws Walk. This annual walk for doggos and their owners raises money for the RSPCA in their efforts to rescue, rehabilitate and rehome animals across Australia. Sydney walkers will be romping around Cathy Freeman Park.

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Audience at TEDxSydney 2017
Photograph: Supplied
Things to do, Talks and discussions

TEDxSydney

icon-location-pin International Convention Centre, Darling Harbour
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TEDxSydney will be inviting creatives, industry change-makers and cultural leaders to share their insights in relation to the theme of ‘legacy’. What will this amount to? A full day of talks and performances exploring humanity’s past triumphs and failings, what the future may hold and what we want to be remembered for.

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Winyanboga Yurringa Belvoir 2019
Photograph: Daniel Boud
Theatre, Drama

Winyanboga Yurringa

icon-location-pin Belvoir St Theatre, Surry Hills
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In 1981, a groundbreaking miniseries called Women of the Sun aired on SBS, telling the story of four Aboriginal women living in Australia between the 1820s and 1980s. Andrea James’ new play was inspired by the series and acts as a kind of fifth chapter, adding another generation to the fold.

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The singer Hatchie in a great jacket with embroidery.
Photograph: Supplied
Music, Pop

Hatchie

icon-location-pin The Lansdowne Hotel, Chippendale
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Hatchie’s creations are the kind you listen to when you’re pinning after a prospective love interest or trying to forget past heartache. Her debut EP Sugar & Spice went through the full rotation of love found and lost, and her new album Keepsake will keep riding that emotional rollercoaster. 

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Nina Oyama Needs a Lift 2019
Photograph: Supplied
Comedy, Stand Up

Nina Oyama Needs a Lift

icon-location-pin The Factory Theatre, Marrickville
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Nina Oyama is making her solo stand-up show debut with this set about her journeys as a black market taxi driver. But she’s definitely not a newcomer to comedy, having appeared at Just For Laughs at the Sydney Opera House, on the ABC series Utopia, and as a reporter for Tonightly with Tom Ballard.

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Stall holder at the Westies Markets displaying her fashion designs
Photograph: Supplied
Shopping, Markets

The Westies Markets

icon-location-pin Nepean Creative and Performing Arts High School, Western Sydney
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The non-for-profit collective behind this quarterly market, the Westies, is all about showcasing the Penrith region while giving local growers and makers the opportunity to sell their products. They want to create a lazy Sunday atmosphere, where you get to know the community rather than fight over the bargain bin.

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People showing their artworks in an art class.
Photograph: Supplied
Things to do, Classes and workshops

Boozy Finger Painting

icon-location-pin Work-Shop Sydney, Chippendale
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This pop-up painting course at Redfern’s Workshop HQ replaces brushes and sponges with your very own phalanges, so you can get really messy making some high concept (read: indistinguishable) artworks. You'll be given step-by-step instruction in creating a specific masterpiece, but in the end you wield creative control.

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People shopping at Sydney Writers' Festival 2018 Carriageworks
Photograph: Prudence Upton
Things to do, Fairs and festivals

Sydney Writers’ Festival

icon-location-pin Carriageworks, Eveleigh
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Each year Sydney welcomes hundreds of authors, journalists, writers and public intellectuals to speak at the weeklong festival. This year, artistic director Michaela McGuire is inviting 45 international guests and 350 homegrown writers to Carriageworks, and other venues across Sydney. See more of the program in May.

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Stephen K Amos: The Story So Far 2019
Photograph: James Penlidis
Comedy, Stand Up

Stephen K Amos: The Story So Far

icon-location-pin Multiple venues
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Comedy giant and honorary Australian Stephen K Amos is back with a show that’s all about the last ten years on stage. It will feature new material alongside some classic bits and the incisively funny – but never threatening – audience participation for which Amos is best known. 

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MCA Artbar 2015 Vivid Sydney edition curated by Rebecca Baumann image feat artwork by Rosie Deacon (c) Museum of Contemporary Art Australia photographer credit Jacquie Manning
Art, Digital and interactive

MCA Artbar

icon-location-pin Museum of Contemporary Art (MCA), The Rocks
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The MCA's party series used to be held once a month, but as of 2019 is only taking place four times a year. It's the same basic idea: a night curated by a different artist or collective each edition, featuring art, performance and design – with killer views, party tunes and hands-on activities with artists.

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at Finders Keepers Market
Shopping, Markets

Finders Keepers

icon-location-pin The Cutaway, Barangaroo
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Australia’s longest running indie design and art market is returning to the Barangaroo Cutaway for three days of refreshing retail that'll match the cool kick of May weather. A line-up of more than 200 stallholders will show off their handcrafted and meticulously designed goods. 

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Jane Goodall's profile.
Photograph: Supplied
Things to do, Talks and discussions

Dr Jane Goodall: Rewind the Future

icon-location-pin International Convention Centre, Darling Harbour
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The work of anthropologist and primatologist Dr Jane Goodall has become synonymous with animal welfare and environmental conservation. In this discussion, Goodall will reflect on her contributions to science and consider humanity’s role in correcting the course climate change.

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Lou Wall's Drag Race - Melbourne Fringe 2018
Photograph: Alexis Desaulniers-Lea
Theatre

Batch Festival

icon-location-pin Multiple venues
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Griffin Theatre Company has been churning out new Australian plays for more than three decades, but what about the creations that don't quite fit into the neat and tidy "play" category? Last year it launched the brilliant Batch Festival, an alternative performance festival that features everything from plays to poetry, burlesque and comedy.

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Jan van de Stool: Parting the Red Curtains 2019
Photograph: James Penlidis
Comedy, Stand Up

Jan van de Stool: Parting the Red Curtains

icon-location-pin Giant Dwarf, Redfern
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Jan Van de Stool is an international musical therapist and the alter-ego of musical theatre and cabaret star Queenie van de Zandt. If you’re into character-based comedy, killer singing and showtunes, head along to one of the Woy Woy-based guru's “workshops”.

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People running in a fun run dressed in pink.
Photograph: Supplied
Sport and fitness, Running

Mother's Day Classic

icon-location-pin Around Sydney, Sydney
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This year marks the 22nd anniversary for the fun run that raises money for the National Breast Cancer Foundation. There are two courses to have a crack at in Sydney: one around Mrs Macquarie's Chair and one in Parramatta Park. You’re encouraged to donate or commit to fundraising when you register. 

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Athlete and model Casey Legler in black and white photo
Photograph: Peter Lindbergh
Things to do, Talks and discussions

Casey Legler: Godspeed

icon-location-pin Carriageworks, Eveleigh
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Former French Olympic swimmer and the first woman to sign a male modelling contract with Ford Models, Casey Legler, has an interesting life story to share. Legler will be at the Sydney Writers’ Festival to talk about their unflinching memoir that covers the public life of a competitive swimmer and the private struggle of alcohol and substance abuse.

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Nazeem Hussain: Basic Idiot 2019
Photograph: Supplied
Comedy, Stand Up

Nazeem Hussain: Basic Idiot

icon-location-pin The Enmore Theatre, Newtown
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In the last year, Nazeem Hussain became a father, starred in his own sketch series (Orange is the New Brown), and scored a stand-up special on Netflix. Now he’s returning to his stand-up roots with a show that’s sure to tackle all of the recent developments in his life. 

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Head On Photo Festival 2019
Photograph: Dina Golstein
Art, Photography

Head On Photo Festival

icon-location-pin Around Sydney, Sydney
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This year Head On Photo Festival is turning ten and bringing out some big guns to celebrate, with 12 international photographers headlining at exhibitions across the city. Six of those will be showing at the festival's hub at Paddington Town Hall, while others will be spread across town.

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Nick Murphy with yellow flowers in his mouth (weird).
Photograph: Supplied
Music, Pop

Nick Murphy

icon-location-pin The Enmore Theatre, Newtown
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The seven-time ARIA Award-winning Melbourne artist formerly known as Chet Faker has made monumental leaps of success since his cover of Blackstreet’s ‘No Diggity’ went viral in 2011. The electro-soul music maker will showcase this artistic development and his new album Run Fast Sleep Naked in Sydney on May 14. 

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Head shot of Omar Musa.
Photograph: Supplied
Things to do, Talks and discussions

Vivid After Hours at AGNSW

icon-location-pin Art Gallery of NSW, Sydney
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We’re a big fan of the Art Gallery of NSW’s free Wednesday night art series. But for Vivid, they’re curating some pretty special nights, each led by a discussion about personal histories, spirituality and cultural and social identity, before art-seeking night owls enjoy live music, interactive workshops and gallery excursions. 

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Alice Fraser Mythos 2019
Photograph: Supplied
Comedy, Stand Up

Alice Fraser: Mythos

icon-location-pin The Enmore Theatre, Newtown
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Alice Fraser is an ex-corporate lawyer who quit the profession when she found she was writing more jokes than contracts. She’s had a fast rise in comedy, having gained a significant following thanks to her stand-up gigs and podcasts. Her upcoming show is all about the lies we tell about ourselves.

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Spanish Film Festival
Photograph: Supplied
Film, Film festivals

Spanish Film Festival

icon-location-pin Multiple venues
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This year's festival arrives with one big change – the Cine Latino Film Festival has been added to the run, providing an enriched experience for those who want to get their Spanish-speaking film fix in one place. On top of that, the biggest Spanish film of the year, Campeones (Champions), is opening the festival nationwide. 

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People taking photos of the nights sky from a lookout in the bush.
Photograph: Richard Bulley Photography
Things to do, Classes and workshops

Astrophotography Nightscape Workshop

icon-location-pin Wentworth Falls,
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In this photography course, you'll learn how to immortalise nightscapes through a lens. Keen astrophotographer Steven Morris will be teaching you how to focus manually on the stars, expose those shining beauties at the right level, shoot panoramic nightscapes, choose the correct lens for the job and read the tonal values on your histogram. 

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33
Author Kristen Roupenian (Cat Person) looking at the camera
Photograph: Urszula Soltys
Things to do, Talks and discussions

Kristen Roupenian: Cat Person and Other Stories

icon-location-pin Carriageworks, Eveleigh
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Remember the wave of excitement when The New Yorker published short story ‘Cat Person’, their most shared piece of fiction in the website’s history? Writer Kristen Roupenian is following up on her viral short story with her debut collection of funny and explicit stories exploring gender, sex and power.

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Sydney Comedy Festival
Comedy

Sydney Comedy Festival

icon-location-pin Around Sydney, Sydney
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Sydney Comedy Festival will continue its take-over of key Inner West venues in May, with a line-up of international, local and interstate comedians across all genres. While not quite as big as its Melbourne counterpart, the Sydney Comedy Festival is still packed with goodies and plenty of high-profile acts.

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Glasses of sparkling wine.
Photograph: Supplied
Things to do, Fairs and festivals

Sparkling Sydney

icon-location-pin Pirrama Park, Darling Harbour
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Our harbourside town is a primo spot to toss back a prosecco with brunch or a sneaky sparkling accompanied by a salty oyster. So it feels very appropriate that a festival honouring sparkling wine will soon arrive at our shores. It'll offer tastings of more than 60 fizzy pours plus a gin bar and gourmet snacks.

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MCA Sculpture Terrace outdoors music
Photograph: Sam Whiteside
Music, Rock and indie

Sounds on the Terrace

icon-location-pin Museum of Contemporary Art (MCA), The Rocks
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Newtown beer barons Young Henrys will be joining forces with the MCA for this season of mid-week art and music parties. The free gigs coincide with the gallery's Wednesday night Lights on Later program, which sees the MCA swing open its doors until 9pm.

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Audrey Hepburn in Breakfast at Tiffany's
Photograph: Supplied
Film, Special screenings

Breakfast at Tiffany's in Concert

icon-location-pin Sydney Opera House, Sydney
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These days, no one would invent a romance for the movie that did not exist in Truman Capote’s source novella, and certainly nobody would cast a white actor in a Japanese part. And yet Blake Edwards’ film exercises an appeal that is truly iconic. Now the Sydney Symphony is presenting Breakfast at Tiffany’s in Concert.

The 50 best bars in Sydney right now

'Tis the season to carb load

Spaghetti prawns at Fratelli Paradiso
Photograph: Anna Kucera
Restaurants, Italian

The best Italian restaurants in Sydney

While good pizzerias and dirt-cheap red sauces places are harder to find than the poshest stuff, there are still spades of options to choose from. We've picked our favourites from every style.

More to explore

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