May in Sydney arrives with a calendar that refuses to slow down. As the city edges into winter, it lights up (literally) with blockbuster festivals, major exhibitions and a packed lineup of gigs, markets and one-off events that make it one of the most exciting months of the year to get out and about.
From citywide spectacles like Vivid Sydney to cultural heavyweights like the Archibald Prize Exhibition, plus live music, the continuing Sydney Comedy Festival, food pop-ups and even a meteor shower overhead, there’s no shortage of reasons to fill your schedule.
Our city will also be welcoming a whole host of celebrity guests, including the iconic Michelle Obama, the king of dark humour, Jimmy Carr, K-pop queens i-dle and trailblazing female rapper, Lil’ Kim.
Whether you’re chasing late-night lights, planning a weekend market crawl or just looking for something new to do, here’s everything worth adding to your May hit list.
Things to do in Sydney in May
Sydney Staples
Vivid Sydney
The 16th annual Vivid Sydney will take over Sydney this May, once again transforming the city into a smorgasbord of light, music, ideas and food with its world-famous projections, provocative installations and on-the-pulse programming. With the return of its famous drone show, a stacked food program and the introduction of Vivid Minds, this edition of the festival is set to be bigger and brighter than ever.
Where: Citywide.
When: May 22-June 13.
Price: Over 80 per cent of the program is free.
The Archibald Prize Exhibition
Presented by the Art Gallery of New South Wales, the Archibald Prize, Wynne Prize and Sulman Prize offer a vivid snapshot of contemporary Australian art and culture. The Archibald Prize, the country’s most prestigious portrait award, recognises outstanding depictions of notable figures from the worlds of music, journalism, media, stage and screen.
Among the country’s most anticipated exhibitions, the annual showcase returns from May 9 to August 16, after the finalists are announced on Thursday, April 30. Featuring works by some of Australia’s most celebrated artists, it remains an unmissable highlight of the arts calendar.
Where: Art Gallery of NSW, Naala Nura building, lower level 2.
When: May 9-August 16.
Price: Adult tickets start at $30.
AFC Australian Fashion Week
This year, Australian Fashion Week (AFW) will take place at the Museum of Contemporary Art, featuring runway shows, talks, workshops, activations and more. While AFW is an invitation-only industry event, the 2026 edition will feature plenty of opportunities for Sydneysiders and visitors to attend shows, talks and workshops.
Fashion fiends can also enjoy the AFW hub for free, which will feature livestreams of events and information on partner activations. Simply register for the Fashion Pass for early access to tickets, live streams and an invitation to attend the official Welcome to Country opening.
Where: Museum of Contemporary Art, 140 George St, The Rocks NSW 2000.
When: May 11-15.
Price: Prices vary for entry to shows, but you can register for the Fashion Pass for free.
Great Southern Nights
Great Southern Nights is a NSW Government initiative launched in 2020 to support the state’s live music, entertainment and hospitality sectors. This year’s program features more than 300 gigs across the state, including standout Sydney shows from Jessica Mauboy at City Recital Hall, Shady Nasty at Vic on the Park, and Hatchie at The Vanguard.
One of the standout features of Great Southern Nights is its Gig Trails, where pubs, bars and venues team up to create curated routes of live music, drinks and dining. On May 9, Chippendale hosts a special trail, followed by another weaving through Newtown and Enmore on May 16. You can check out the full Great Southern Nights program here.
Where: Great Southern Nights hosts gigs all over NSW.
When: May 1-17.
Price: Some shows are free with an RSVP, while others are ticketed.
Sydney Comedy Festival
The Sydney Comedy Festival keeps the laughs rolling across the city through the first half of May, wrapping up on May 17. From big-name international acts to rising local comics, the program serves up something for every sense of humour.
Highlights this month include the Comedy Cruise on May 9, a harbour spin with drinks and a stacked comedy lineup, plus the ever-popular Comedy Crawls, which are basically just bar hops where you laugh a lot more than usual. You can also catch Sh!tfaced Shakespeare at Darling Quarter Theatre, alongside a packed schedule of multi-comic showcases running through the festival’s final weeks.
Where: Citywide.
When: April 13-May 17.
Price: Ticket prices vary, with some shows free.
Sydney Writers’ Festival
Delivering over 200 events from more than 250 authors, the Sydney Writers’ Festival will transform the city into a week-long celebration of storytelling this May.
Headline festival guests include former New Zealand Prime Minister Jacinda Ardern, who will discuss her path to global leadership and speak on her deeply personal memoir A Different Kind of Power. Yann Martel, the Author of Life of Pi, shares his latest book, Son of Nobody, which reimagines the Trojan War. You can check out the full program here.
Where: Main hub: Carriageworks (245 Wilson Street, Eveleigh), other key venues include Sydney Town Hall, State Library of NSW, and community libraries.
When: May 17-24.
Price: Tickets generally range from $25 to $75.
Spot shooting stars above Sydney
The Eta Aquariids meteor shower will make its way across Sydney’s sky from late April to early May again this year, creating a celestial spectacle before sunrise. Formed from trails of debris left behind by Halley’s Comet, this meteor shower is regarded as one of the strongest in the Southern Hemisphere.
Astronomy enthusiasts should set their alarms for 2am and 5:45am on Thursday, May 7, when viewing conditions are expected to be at their peak for spotting shooting stars.
Where: Visible across Sydney, although you should head to the Blue Mountains for the best view.
When: Viewing conditions are best at 2am and 5:45am on Thursday, May 7.
Price: Free to watch (obviously).
Must-visit Markets
The Great Artist Market
Kicking off at 8am this Saturday, The Great Artist Market will take over Felons Barrel Room on Manly Wharf until 3pm. More than 40 artists and makers have been selected to take part in the waterfront market, selling everything from handmade glass pieces and functional ceramics to contemporary paintings.
Where: The Great Artist Market, Felons Barrel Room.
When: May 2, 8am-3pm.
Price: Free entry.
The Pyrmont Festival
The Pyrmont Festival returns to Pirrama Park on May 23 and 24, bringing together more than 25 wineries, breweries and distilleries alongside some of the best produce from across NSW. Think cheese, chilli oil, chocolate, seafood and premium meats. Beyond the tasting stalls, expect a kids’ zone, family-friendly entertainment, food and wine masterclasses, art workshops and more. The best part? Entry is free.
Where: Pirrama Park, Pirrama Road, Pyrmont.
When: May 23 and 24, 11am-5pm.
Price: Free entry.
The Finders Keepers Sydney Design Market
Beloved institution, The Finders Keepers Market returns to Carriageworks for the entire weekend. As always, the large-scale event is the ultimate collection of Australia’s best and brightest designers, including indie labels ready to showcase their latest projects.
The design market is always such a big shopping event for Sydney’s well-dressed that organisers make a full day of it with live local DJs, fresh food stalls, pop-up bars and more shopping than you could ask for.
Where: Carriageworks, 245 Wilson St, Eveleigh NSW 2015.
When: May 1-3, Friday: 4pm-9pm, Saturday: 10am-5pm, Sunday: 10am-5pm.
Price: From $7.
Barangaroo Artisan Market
The Streets of Barangaroo will turn into a bustling marketplace on Mother’s Day weekend, serving up a day of entertainment, food and shopping. Over 70 artisan stallholders will sell a curated selection of locally made goods, from handcrafted jewellery, textiles and ceramics to chocolate, candles and unique gifts.
The markets will also bring in an exciting lineup of roving entertainment, gourmet food offerings and a dynamic DJ set from deep house duo YDKR (Rick and Johnny) and experimental saxophonist Gab Zak.
Where: Barangaroo Artisan Markets, The Streets of Barangaroo, Barangaroo Ave, Barangaroo NSW 2000.
When: May 9, 10am-3pm.
Price: Free.
Watsons Bay Autumn Market
One of Sydney’s most scenic markets returns for its autumn edition, set against the stunning harbour backdrop of Watsons Bay. Featuring over 150 stalls, visitors can peruse artisan products, jewellery, fashion, fresh produce, gourmet food and sweet treats, while younger market-goers can enjoy kids’ rides and family-friendly entertainment.
Where: Robertson Park, Watsons Bay.
When: May 31, 9am-3pm.
Price: Free entry.
Wentworth Point Autumn Market
The Wentworth Point Autumn Market lands this Sunday, bringing a lively mix of curated stalls to the waterfront community, which is just a short walk from Sydney Olympic Park. Expect family-friendly entertainment, free kids’ activities, and a strong lineup of food and drink vendors, alongside local businesses showcasing their goods.
Where: Wentworth Point Town Square.
When: May 3, 9am-3pm.
Price: Free entry.
Where to Eat and Sip
Mezcal May at Cantina OK!
Self-described “Micro Mezcal Mecca” Cantina OK! serve Sydneysiders world-renowned margaritas and cocktails with hand-shaved ice and hand-pressed limes. This May, the MUCHO Group bar is serving up its rare agave spirits for a fraction of the usual price, with a trio of hand-selected mezcals available for just $10 each all month long.
We can’t wait to try their ‘Bondi Beach’ Mezcal, which has been discounted from $28 to $10, transported from San Luis Amatlán in southwestern Mexico.
Where: Council Pl, Sydney NSW 2000.
When: All of May.
Price: $10 each for the Mezcal.
Free cone day at Ben & Jerry’s
Ben & Jerry’s is serving up free scoops for one day only, on Thursday, May 5. Free cone day has actually been a thing since 1979, when the ice cream team thanked its customers with free scoops from its first outpost in a renovated gas station in Burlington, Vermont.
Now available to ice cream lovers across Australia and Sydney, you can head to their stores in Darling Harbour, Hoyts Broadway, Bondi Beach, Manly, Parramatta and Hoyts Blacktown to grab your free scoop, no strings attached.
Where: Available at stores in Darling Harbour, Hoyts Broadway, Bondi Beach, Manly, Parramatta and Hoyts Blacktown.
When: May 5, 12pm-8pm.
Price: Free.
Fever-Tree G&T Week
Celebrate the beautiful creation that is a gin and tonic this month as part of Fever-Tree G&T week, which will run from May 18-24. Bars, restaurants and distilleries across Sydney will showcase G&T serves with curated menus and special pricing. Participating venues include the iconic Icebergs Dining Room and Bar in Bondi, Ester Spirits in Marrickville, Duke of Clarence in the CBD and Silvers Motel in Enmore.
The week also includes the inaugural Fever-Tree G&T Cup, a competition to crown the best gin and tonic in Australia and New Zealand, plus a chance for attendees to win a year’s supply of G&Ts.
Where: Citywide.
When: May 18-24.
Price: Free entry.
Mother’s Day dining specials
Mother’s Day falls on Sunday, May 10 this year, so make sure you’ve got your plans in order, so you can commemorate her special day with some quality time (and delicious food). We’ve rounded up the best high teas in Sydney, from boujie spreads and live opera at the Castlereagh Hotel to a decadent, English-style offering at the Langham.
If high teas are not her thing, treat your mumma to lunch at one of these top Sydney venues, which are offering up limited-edition Mother’s Day menus to make her day extra special.
Where: Citywide.
When: Sunday, May 10.
Gigs, Concerts and Talks
In Conversation with Michelle Obama
One of the most inspirational and compelling women of our century, Michelle Obama, is gracing Sydneysiders with her presence at the TikTok Entertainment Centre. She’ll be appearing to audiences in Sydney and Melbourne for the first time, sharing her extraordinary story from her childhood on the South Side of Chicago to her years in the White House.
Where: TikTok Entertainment Centre, 14 Darling Drive, Sydney, NSW, 2000.
When: May 20 and 21 at 7:30pm.
Price: From $195.
Jimmy Carr
One of Britain’s most popular comedians, famed for his one-of-a-kind laugh and dark humour, Jimmy Carr will take to the stage for two comedy shows at Darling Harbour Theatre this May. His brand-new tour, Laughs Funny, is sure to be packed full of hilarious, fast-paced jokes and edgy one-liners that will have you cackling and groaning. Tickets are sure to sell out, so make sure to secure them now!
Where: Darling Harbour Theatre at ICC Sydney, Sydney, NSW 2000.
When: May 10, 6:45pm and 9:45pm.
Price: Tickets from $91.65.
Beck
Genre-defying musician Beck heads to Sydney in May for three nights performing with the Sydney Symphony Orchestra. Expect sweeping arrangements and cinematic reinterpretations from his back catalogue of much-loved hits from albums including Sea Change, Mutations, and Odelay, plus the odd surprise cover or two.
Only a handful of tickets remain, but it’s worth trying to secure one if you can.
Where: Concert Hall, Sydney Opera House.
When: May 7, 8, 9.
Price: From $110.
Thundercat
Los Angeles bassist, singer and producer brings his genre-defying sound to the Hordern Pavilion for one night only after the long-awaited release of his album Distracted.
The Grammy-winning artist, known for his collaborations with Kendrick Lamar and Flying Lotus, blends jazz, funk, soul and electronic music into something entirely original and his own. Expect six-string bass solos (lots of them), falsetto vocals, and tracks from his early catalogue.
Where: The Hordern Pavilion, Driver Ave, Moore Park NSW 2021.
When: May 13.
Price: From $99.90.
Peking Duck
This Hordern Pavilion gig marks a landmark Sydney homecoming for Peking Duck, as the band debuts brand-new music plus a new live show with epic in-the-round production.
The electronic duo is made up of Reuben Styles and Adam Hyde, who also perform under the name Keli Holiday and are behind the smash-hit “Dancing2”. They’ll both be bringing that signature Peking Duck energy to Hordern Pavilion for their special, one-night-only show.
Where: Hordern Pavilion, Gate C/3 Driver Ave, Moore Park NSW 2021.
When: May 15.
Price: From $74.99.
KT Tunstall
Live out your The Devil Wears Prada fantasy as you bop along to KT Tunstall’s “Suddenly I See” at the Metro Theatre. She’s celebrating the 20th anniversary of her groundbreaking, multi-million-selling debut album, Eye To The Telescope, and will play the five-times-platinum album in its entirety.
The Scottish singer-songwriter has a whole heap of iconic noughties songs (like “Black Horse and the Cherry Tree”) that will be sure to get the nostalgic crowd dancing.
Where: G2/624 George St, Sydney NSW 2000.
When: May 23.
Price: From $89.90.
i-dle
i-dle are heading Down Under for their fourth global tour, 2026 i-dle WORLD TOUR [Syncopation], set to light up Qudos Bank Arena for a one-night-only spectacle that’s sure to be on every K-pop fan’s radar (just ask their 13.3 million Instagram followers).
Renowned for their bold, empowering concepts and viral hits like Tomboy, Queencard and Nxde, the group continues to defy industry norms. With a hands-on approach to songwriting and production, i-dle have carved out a distinct creative identity, cementing their status as one of South Korea’s most influential and successful girl groups.
Where: Qudos Bank Arena, 19 Edwin Flack Ave, Sydney Olympic Park NSW 2127.
When: May 30, 7:30pm.
Price: From $189.
Lil’ Kim
Lil’ Kim will be performing a huge landmark show as part of Vivid Sydney 2026, taking over Carriageworks for a huge show on May 29. The trailblazing female rapper changed the music industry, with her bold sexuality, killer confidence and undeniable talent.
She’ll be celebrating her two albums, Hard Core and The Notorious K.I.M., in Carriagework’s iconic warehouse-style music space, with tickets starting at $99 plus a booking fee.
Where: Carriageworks, 245 Wilson St, Eveleigh NSW 2015.
When: May 29 at 5pm.
Price: From $99, plus a booking fee.
What’s on in Theatre
The Lion King
In very exciting news for Sydney’s theatre fanatics, blockbuster musical The Lion King has returned to the Harbour City. The original Australian production of The Lion King premiered at the Capitol Theatre in Sydney in October 2003, returning for a second run 10 years later in 2013, and is now back again at the iconic venue 13 years later.
You can read our review of the stunning show here.
Where: Capitol Theatre, 13 Campbell St, Haymarket NSW 2000.
When: April 18-August 9, 2026.
Price: From $165.
Anastasia
Since its Broadway debut in 2017, Anastasia has captivated sold-out audiences and collected more than 15 major international awards, and it has now finally made its debut Down Under.
Rising star Georgina Hopson will lead the cast as Anya, alongside international stage sensation Robert Tripolino as Dmitry. Showbiz legend Rhonda Burchmore will take to the stage as Countess Lily, with Australian theatre royalty Nancye Hayes AM as the Dowager Empress.
Where: Sydney Lyric Theatre, Pyrmont.
When: April-July 19.
Price: Tickets from $69.90.
Romeo and Juliet
Watch one of the world’s greatest love stories come to life on the stage of the Joan Sutherland Theatre. Renowned dancer and choreographer John Cranko reimagined William Shakespeare’s iconic tale as a sweeping classical ballet, transforming the stage into medieval Verona and bringing themes of love, rivalry, and tragedy to life.
Whether you’re a devoted ballet enthusiast or new to the art form, it’s a truly captivating production not to miss.
Where: Joan Sutherland Theatre, Sydney Opera House, Macquarie St, Sydney NSW 2000.
When: April 24-May 13.
Price: Tickets from $56.
84 Charing Cross Road
Adapted from Helene Hanff’s beloved non-fiction book, 84 Charing Cross Road comes to life on stage at Ensemble Theatre for a limited season. The story follows a sharp-tongued New York writer and a reserved London bookseller who begin a correspondence over their shared love of rare books, only to discover an unexpected lifelong friendship.
Where: Ensemble Theatre, 78 McDougall St, Kirribilli NSW 2061.
When: May 1-June 13.
Price: Adult tickets start at $95.
An Iliad
A weary, sharp-tongued poet (played by international star David Wenham) takes the stage at Wharf 1 Theatre to retell the story of the Trojan War, a tale he has carried across centuries of human conflict.
In Lisa Peterson and Denis O’Hare’s powerful adaptation of Homer’s epic, the ancient myth is reimagined as an intimate, urgent reflection on war, division, and humanity’s enduring cycles of violence.
Where: Wharf 1 Theatre, The Wharf, Wharf 4/5/15 Hickson Rd, Dawes Point NSW 2000.
When: April 13-June 21, 2026.
Price: Tickets from $79.
The River
Miranda Otto returns to the stage with Sydney Theatre Company in The River, a haunting and intimate drama by acclaimed playwright Jez Butterworth. Set in a remote cliffside cabin, the play follows a fisherman (Ewen Leslie) and a woman whose romantic weekend begins to unravel as unsettling truths emerge.
Directed by Margaret Thanos and co-starring Andrea Demetriades, the production blends poetry and mystery to explore love, intimacy, and human connection.
Where: Drama Theatre, Sydney Opera House, Sydney NSW 2000.
When: April 13-May 16.
Price: Tickets from $59.
Cluedo The Play
Cluedo, the iconic whodunnit that has long captivated audiences on the tabletop and on screen (including the 1985 film from Paramount Pictures), has arrived on stage in Sydney.
When six intriguing guests gather at Boddy Manor, secrets unravel, and murder is on the menu, with the audience invited to piece together the mystery. Packed with sharp wit, twists, and theatrical flair, Cluedo delivers a laugh-out-loud night of suspense that will keep you guessing until the very end.
Where: 108 King St, Sydney NSW 2000.
When: Playing until May 10.
Price: Tickets from $69.90.
Sport and Events
NRL State of Origin, Game 1
The NRL State of Origin series is one of Australia’s greatest sporting rivalries, as the NSW Blues take on the QLD Maroons. As rugby league boss Peter V’landys puts it, “State of Origin isn’t just a football match – it’s a cultural phenomenon.” NSW will be looking to reclaim the series after losing to QLD in 2025, and the all-important Game 1 will be played under lights at Accor Stadium.
While being part of the crowd is a bucket-list experience for any sports lover, tickets can be scarce. Luckily, pubs and clubs from Bondi to Penrith will fire up the big screens, so if you can’t make it to the stadium, standing shoulder-to-shoulder in a packed sports bar is an excellent second-best option.
When: Wednesday, May 27, 2026.
Where: Accor Stadium, 15 Edwin Flack Avenue, Sydney Olympic Park, NSW 2127.
Price: Stadium tickets start from $39.75.
