May sees Sydney fast marching toward winter, which begins next month. The days are shorter, temperatures drop, and it’s unlikely you will swim outdoors this month.

Visiting in May can be great value for money, with accommodation prices low for all but the last week of the month when they begin to rise with events like Vivid starting.

This is a lovely time of year for walking, so check out some of our most popular walks, including The Rock’s self-guided walk and Cremorne Point on the lower north shore of Sydney Harbour.

Average Temperatures: 19.8 – 11.8 °C 54-67 °F
While each year varies the last May saw only one day of rain. This year we are expecting a little more.

New events and updated content are added to these pages as it becomes available. Please contact us if you have an event you would like to share.

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Major Annual Events in May

• Vivid Sydney – 24 May – 15 June 2024
• Sydney Writers Festival – 20-26 May 2024
• Australian Fashion Week
• Mother’s Day – Sunday 12 May

Check out our guide to the best places to head for Mother’s Day dining

Sydney Writers Festival

With a range of free and ticketed events the Sydney Writers Festvial is accessible to all.With 309 writers appearing as part of the event you are bound to find something of interest.

Highlights include:

• Australia’s largest poetry slam, The Bankstown Poetry Slam ($25)
• Jake Adelstein – Author of Tokyo Vice and his new book Tokyo Noir ($25)
• Phosphorescence author Julia Baird talking about her new novel Bright Shining.
• Bonnie Garmus author of Lessons in Chemistry ($40)

The full program is available here.

When: 20-26 May 2024
Where: Sydney Town Hall, Sydney Opera House, Carriageworks and more

Vivid Sydney

Quite possibly the most popular event in Sydney. The Vivid Festival sees art installations and 3D projections light up the city’s landmarks.

But it is so much more. This year the festival’s theme is Humanity and along with the art and projections the theme will be live music and performances showcasing a mix of emerging and well-known artist.

Delight in the diversity of flavours at pop-up markets and dining events, celebrating our community’s cultural richness.

When: 24 May – 15 June 2024
Where: Sydney Town Hall, Sydney Opera House and more

Afterpay Australian Fashion Week (AAFW)

Celebrate Afterpay Australian Fashion Week with a week of non-stop style featuring some of Australia’s top fashion labels. Featuring 45 designer runway shows and presentations from new and notable names live at Carriageworks in Sydney showcasing 11 First Nations fashion designers and curated conversations and special events.

When: 13-17 May 2024
Where: Carriageworks

Festivals, Fairs and community events

The Other Art Fair 

The Other Art Fair challenging elitism and embraces diversity. Art breaks free from rules, and so should your experience. No VIP ropes here; everyone is welcome.

Discover a unique blend of affordable art, immersive installations, performances, DJs, and a vibrant bar. Go along and discover recent works by established and emerging artists. 

When: 16-19 May
Where: White Bay Cruise Terminal Rozelle

Cronulla Jazz and Blues Festival

Eleven stages, over 100 artists, and everything from Jazz, Blues, Funk Soul, Alt-Country & Americana. Head to Dunningham Park, Monro Park, street buskers, or one of the ticketed performances at local venues.

When: 29 May – 2 June 2024
Where: Cronulla Street Cronulla l Cost: Most events are free
More: Check the official website for the schedule.

Markets

Woodstock Artisan Market

The perfect opportunity to find a unique gift from the heart for Mum as the pre-Mother’s Day Woodstock Artisans Market is always a very special event.

Filled with quality goods crafted by local makers and designers, there’s no reason you cannot find amazing handmade homewares, jewellery, body care products, gourmet food and wine, ceramics, fashion, art, curios, and much more.

When: 5 May 2024
Where: Woodstock Community Centre, 22 Church St, Burwood
Tickets: Free Entry.

Musicals and Theatre

Death of a Salesman 

This May the Theatre Royal Sydney presents Arthur Miller’s “Death of a Salesman,” featuring Emmy, Golden Globe, and Tony Award-winner Anthony LaPaglia. This production, directed by Neil Armfield, has already received critical acclaim in Melbourne.

Recognised as one of the 20th century’s greatest plays, it stars some of Australia’s top actors, including Alison Whyte and Josh Helman. Don’t miss this timeless masterpiece that has enthralled audiences for generations, promising a theatrical event of a lifetime.

When: 17 May to 16 June 2024
Where: Theatre Royal

Parade 

Set in early 20th century Atlanta, Georgia, amidst the shadows of slavery and the Civil War, the narrative revolves around Leo Frank, a Jew from Brooklyn, accused of the murder of 13-year-old Mary Phagan. Amidst racial tensions and a biased trial, Frank faces condemnation in a conservative society still reeling from the aftermath of the 1906 Atlanta race riots.

Exploiting religious fears, a sensationalist publisher unfairly portrays Frank as a villain using stereotypes. False evidence seals his fate, despite support from a governor and his Jewish wife, who becomes his staunchest supporter, driven by love and conviction.

When:  From 9 May 2024 
Where: Everest Theatre, Seymour Centre, Chippendale
Tickets: From $99 Adult, From $69 Concession, $89 Early Bird, From $79 Preview

Don Juan

Say hello to theatre at its most fun, with Don Juan – a ludicrously sexy tale of the original master of seduction. This gaggle of “French” performers bring together brilliant physical comedy, twisted pop songs and explosive wit for a hilarious and irreverent show.

With rave reviews from Edinburgh to Adelaide, the Fringe comedy darlings from New Zealand (A Slightly Isolated Dog) bring an extra dose of joy and frivolity to Bondi Pavilion this May with Don Juan. Three nights only!

When: 23 – 25 May
Where: Bondi Pavilion Theatre I Recommended 15+ Strong language and adult themes

& JUliet

“& JULIET” reimagines Shakespeare’s classic tale with a twist, asking what if Juliet’s story began where Romeo’s ended. This new, humorous, and touching musical comes from an Emmy-winning writer of “Schitt’s Creek,” offering a fresh perspective on self-discovery and second chances.

The Australian cast is led by the talented Rob Mills, Casey Donovan, and Amy Lehpamer, with Lorinda May Merrypor shining in the title role of Juliet.

The musical is not just a compelling story but also a celebration of pop music, featuring songs from Katy Perry, Britney Spears, The Backstreet Boys, Ariana Grande, Pink, Justin Timberlake, and more.

When: Opening 27 February – on sale now until 12 May 2024
Where: Lyric Theatre, The Star Sydney

Into the shimmering world

Into the Shimmering World is a moving Australian tale of love and renewal, set against the backdrop of life on the land, featuring performances by Colin Friels and Kerry Armstrong. They portray Ray and Floss, a farming couple whose enduring partnership is tested by the challenges of a severe drought, leading them to the brink of significant change.

This production captivates with its gothic, dreamlike portrayal of the Australian landscape, rich, musical language, and a profound examination of the Australian spirit.

When: 2 April to 19 May 2024
Where: Wharf Theatre 

A Case for the Existence of God

Outhouse Theatre Co. returns with the much-anticipated Australian premiere of A Case for the Existence of God by Samuel D. Hunter (The Whale).

Awarded Best Play in 2022 by New York Drama Critic’s Circle, it is a heart-wrenching, compassionate and achingly funny exploration of empathy that investigates the connection between two very different men, both experiencing a hostile and divided world.

When: 11 Apr – 4 May
Where: Seymour Centre

NO PAY? NO WAY!

“No Pay? No Way!” returns to the Drama Theatre after its acclaimed 2020 debut, celebrated for its humour and timely satire. Directed by Sarah Giles and adapted by Marieke Hardy, this farcical comedy, originally penned by Italian playwright Dario Fo, tackles the absurdities of economic struggle.

The story follows Antonia, portrayed by Mandy McElhinney, and her riotous revolt against rising prices, leading to a shoplifting spree and comedic chaos. With a stellar cast, including Glenn Hazeldine and Aaron Tsindos, this production promises relentless laughter and sharp social commentary, proving more relevant than ever in today’s world.

When: 6 April – 11 May 2024
Where: Drama Theatre Sydney Opera House 

Ulster American

Jay is the Oscar-winning actor. Leigh is the ambitious director. Ruth is the young playwright with a gritty historical drama that is destined to make them the talk of Tinsel Town.

With the shiny accolades of Hollywood within their clutches, the three rendezvous to secure the play and discuss the nitty gritty – but when boundaries are broken, the night collapses into full-blown chaos. The show must go on!

When: 13 May – 8 June 2024
Where: Ensemble Theatre, 78 McDougall Street, Kirribilli
Tickets: $43-88

Music, and Dance

Momenta – Sydney Dance Company

Momenta is a breathtaking exploration of human connection by renowned choreographer Rafael Bonachela. This enthralling dance piece showcases a dynamic range of energies, encapsulating the fleeting nature of moments caught between the past and future, where paths intersect and merge.

Characterised by Bonachela’s signature rhythmic and spatial patterns and creative partnering, “momenta” features Sydney Dance Company performers, pushing beyond their physical bounds with elegance, strength, and openness.

When: 28 May – 8 June 2024
Where: Roslyn Packer Theatre

The Vallies Frankie Valli, Motown & Rock ‘n’ Roll

Experience the magic of Sydney’s newest vocal sensation, The Vallies, as they bring to life the timeless sounds of Frankie Valli and The Four Seasons, Motown, and more.

Featuring top Australian talent from hit productions like Wicked and Jersey Boys, this dynamic show is not to be missed.

When: 11 May 8pm  I Tickets – $25
Where: Bankstown Sports Club 

Mark Vincent in Concert

An enchanting evening with Mark Vincent, Australia’s Got Talent 2009 winner, as he entertains with his celebrated repertoire.

From classical crossover to acclaimed musical theatre performances, including roles in Dirty Dancing and My Fair Lady directed by Dame Julie Andrews, Vincent’s talent shines bright on stage. 

When: 18 May 8pm  I Tickets – $49
Where: Bankstown Sports Club  

‘We Honestly Love You’ – Celebrating the life and music of the unforgettable Olivia Newton-John

A soulful tribute to the unforgettable Olivia Newton-John by Susannah Mirana. Prepare to be transported to the golden era of music with Susannah Mirana’s soulful tribute to Olivia Newton-John.

Backed by a stellar band, Mirana delivers unforgettable hits that have left an indelible mark on generations of music lovers. 

When: 24 May I Tickets – $20
Where: Bankstown Sports Club 

Michael Bublé Experience

Elevate your evening with the mesmerising Michael Bublé Experience, starring Mitch Chapone, Renowned for his mastery in channelling the smooth charisma of Michael Bublé.

Chapone delivers flawless renditions of Bublé’s timeless classics, for an intimate concert experience, akin to being serenaded in your living room.

When: May 26th, 2pm    I Tickets – $25
Where: Bankstown Sports Club 

Sydney Symphony events

With lots of performances in the Opera House Concert Hall, these events are a fabulous addition to your Sydney Itinerary. Tickets start at just $45, making them not much more costly than an Opera House Tour.

A Musical Tempest with John Bell

Conductor Umberto Clerici has curated this special performance with music by great composers inspired by Shakespeare’s The Tempest, presented alongside excepts the play performed by one of Australia’s greatest-ever actors, John Bell. 

When: 2-3 May
Where: Concert Hall, Sydney Opera House

Tchaikovsky’s Fifth Symphony

Indulge in the intoxicating richness of Tchaikovsky’s Fifth’s Romanticism with its passionate melodies and beautiful orchestration, led by internationally renowned conductor Han-Na Chang. 

When: 8-11 May
Where: Concert Hall, Sydney Opera House

When George Met Arnold

When George Met Arnold is a unique event which combines a newly created film with a live performance of selected works by both composers to tell the story of the remarkable relationship of George Gershwin and legendary Viennese composer Arnold Schoenberg. 

When: 15 May
Where: Concert Hall, Sydney Opera House

Joyce Yang Performs Grieg’s Piano Concerto 

Grammy-nominated pianist Joyce Yang brings her ‘vivid and beautiful playing’ (New York Times) to a program that excites on every level with her performance of one of Grieg’s most iconic works.  

When: 18-19 May
Where: Concert Hall, Sydney Opera House

Ngapa William Cooper

A rich new collaboration between composer Nigel Westlake, singer/songwriter Lior and language activist Lou Bennett, Ngapa William Cooper is a tribute to the life of Yorta Yorta activist William Cooper.

This show will also tour regionally to Newcastle and Wyong. 

When: 23 May
Where: City Recital Hall

Comedy

Joe Avati: When I Was Your Age Tour 

Embark on a laughter-filled journey through generational quirks and modern-day parenting with Joe Avati.

Known for his wit and relatable humour, Avati’s show guarantees an evening of entertainment for families and friends alike. 

When: Friday, 10 May, 8.30pm I Tickets – $59.90.
Where: Bankstown Sports Club

Big Fat Loser

“Big Fat Loser” is a one man show in which comedian Mitch Garling shares his current weight loss journey (he is down 50kg) , life as a Dad and just general and very relatable observations of life!

When: 2-3 May
Where: Enmore Theatre Wine Bar

Food and Drink Events

Pyrmont Food and Wine Festival

The Pyrmont Festival is a festival celebrating food, wine, and art, which includes the 2-Day food and wine event. A festival is a community-run event that fosters a strong connection with the country and the city.

When: 18-19 May 2024
Where: Pirrama Park Pyrmont l Free entry

Sydney Spirits Festival

The Sydney Spirit Festival is the largest and most diverse gathering of spirits in Australia.

The event will showcase 148 brands spanning whisk(e)y, gin, soju, schnapps, rum, agave, vodka, vermouth, grappa, tequila, liqueurs, fortified wines. You will also have the chance to join exclusive masterclasses. 

This is your chance to explore rare and award-winning spirits from international and boutique distillers. Hear from renowned figures in the industry, including the Godfather of Whisky, Bill Lark.

Along with all the amazing drinks on offer will be six food stands offering international cuisines.

When: 10-12 May
Where: Overseas Passenger Terminal, Sydney Cove l Tickets: $80 per 3-hour session.

Tas Whisky Tasting Night

Whisky enthusiasts will want to grab tickets quick smart to this very special event. With six fantastic expressions of Tassie whisky lined up for a night of tasting at Different Drummer Bar in Glebe.

You will be guided through an explorative and informative tasting of each unique whisky, given the chance to take your own notes, and engage in conversation with your peers. A great night to integrate and educate the whisky community!

When: 13 May 6:30pm-8:30pm
Where: Different Drummer Bar- 185 Glebe Point Road, Glebe l Tickets: $65 here

Art & Exhibitions

World Press Photo Exhibition 2024

One of the most popular exhibitions staged at the State Library each year the 67th annual World Press Photo Contest is a globally acclaimed exhibition showcasing the pinnacle of photojournalism and documentary photography from the past year.

With a staggering 61,062 entries from 3,851 photographers spanning 130 countries, this year’s winners have emerged from a fierce competition.

Celebrating excellence in storytelling through imagery, the spotlight shines brightly on two Australians making waves in the Southeast Asia and Oceania region: Eddie Jim, a standout in the Singles category, and Aletheia Casey, making her mark in the Open Format category.

When: 25 May to 7 July 2024
Where: State Library NSW, Macquarie Street Sydney I Free

MCA Up Late

Sounds on the Terrace is back for another season. Head to the rooftop of the MCA for live performances and music, or enjoy cocktails with a harbour view. Before you head up check out the current exhibitions, entry is free.

When: Fridays in May
Where: Museum of Contemporary Art, 140 George Street, The Rocks

White Rabbit Gallery – A Blueprint for ruins

“A Blueprint for Ruins” delves into the stark contrast between China’s pursuit of modernisation and the resulting desolation. As cities evolve, sacrificing their soul for skyscrapers, the haunting emptiness asks: where have the people gone? This narrative exposes the paradox of progress—buildings destined for demolition before completion, communities uprooted, leaving behind echoes of displaced lives amidst the skeletal remains of what once was.

When: ends 12 May
Where: 30 Balfour Street, Chippendale NSW l Cost: Free

Sports and Outdoors

The Mother’s Day Classic

Celebrate Mother’s Day and raise funds for breast cancer research. Choose to walk or run either the 4.8km or 7.5km course. The main Sydney event will start from the Domain. The Western Sydney event will start at Lizard Log, Western Sydney Parklands, Abbotsbury with slightly different course lengths on offer.

When: Sunday 12 May 2024
Where: The Domain

Million Paws Walk

The Million Paws Walk event is for fur parents and animal lovers. Whether your pet dog likes to strut, crawl or bolt, they will be more than welcome on this fun-filled day out.

When: 26 May 2024
Where: Various locations in NSW including Sydney

Yoga in the Park

Get fit and flexible every Sunday morning with FREE Yoga in The Park!
The focus on breathing, the concentration required to find balance in certain poses, the flow of the movements – it’s all an active meditation that can help clear the mind, quieten anxieties and strengthen your body.

When: 9:30am, every Sundays(All Year)
Where: Corner of Lower Fort St and George St at Dawes Point Park, right under the Sydney Harbour Bridge.
Tickets: FREE. More Info here 

A-League Men Finals Series

When: TBC
Where: Semi-finals- Allianz Stadium/ Finals- Sydney at CommBank Stadium

Regional Events

The first weekend in May is packed with fabulous regional festivals, so if you are considering an autumn getaway this is a great time to jump in the car and check out regional NSW.

Australian Celtic Festival

Each year at the Australia Celtic Festival they highlight a different area. The 2024 festival will celebrate Ireland and the Isle of Man.

When: 2-5 May 2024
Where: Australian Standing Stones, Glen Innes, NSW

Robertson Potato Festival

It’s time to head to Robertson and join this celebration of the humble potato at the now annual Robertson Potato Festival. While people joke about the town’s Big Potato, which let’s face it is not exactly a draw card, the town’s edible potatoes are something special.

Join in with the fun:

• Cooking demonstrations from leading local chefs and the likes of celebrity chefs including Julie Goodwin
• Competitions with major prizes such as Hessians On The Field, featuring handmade potato sack couture that will strut the catwalk for a chance to win a heavy-duty Singer sewing machine and a cash prize worth $1000. 
• Family-friendly activities and competitions with prizes up for grabs including competitive peeling and mashing, spud ‘n’ spoon races, sack races, spud survivors,s and more.
• Live entertainment from Dragon, and a variety of local musicians and artists

There is plenty to see in the surrounding southern highlands towns, so why not stay a few days?

When: 4-5 May 2024
Where Robertson Showgrounds, 2315 Kangaloon Rd, Robertson
Tickets: Free

Narooma Oyster Festival

Narooma is the heart of Australia’s Oyster Coast, and the Narooma Oyster Festival has won three tourism awards, so you know it’s well worth the drive. Live music, local art and culture, fresh produce, and the world’s best oysters!

When: 4-5 May 2024
Where: Narooma NSW

Ironman Australia Port Macquarie

Australia’s oldest IRONMAN event takes place in the stunning town of Port Macquarie. At the home of the Oceania TriClub Championship, you’ll experience a truly unique swim in the calm water of the Hastings River, a spectacular ride alongside the Pacific Ocean and a high-energy run in the heart of Port Macquarie, with crowds cheering you all the way to the line.

When: 5 May 2024
Where: Port Macquarie

Sail Port Stephens

Sail Port Stephens is an annual yachting regatta held every April on the pristine waters of Port Stephens. The Commodores Cup (PHS) and Port Stephens Trophy (ORC Club) will now run over five days with 27 April retained as the lay day and a major social event planned for Wednesday 26 April.

When: April-May 2024
Where: Port Stephens
More info on their website.

Moree on a Plate

Producers from around the New England North-West Region will turn Moree into a food & wine lover’s delight when they gather in the most productive agricultural shire in Australia, Moree NSW. Come along and enjoy the tasty delights of the region at Moree on a Plate, a relaxed, social day out the whole family can enjoy.

When: Saturday, 11 May 2024
Where: Moree Secondary College Albert St, Moree
Cost: $2

Mudgee Classic Cycling

Set in New South Wales’ beautiful Mudgee wine region, the Mudgee Classic will surely be a bike ride to remember. Catering for all levels of cycling ability, the event offers four courses: 175km Maxi Classic, 125km Challenge Classic, 65km Rouleurs Classic, 55km Dirty Mudgee and the 35km Social Classic. More information 

When: 4-5 May 2024
Where: Mudgee
More info on their website.

Nooroo Garden Open Days

Nooroo Garden is one of Australia’s best-known gardens and showcases the beauty and spectacle of plant and flower species from around the world, as well as Australian native plants. Come along with your family and friends and admire the wonderful maples, forsythia, liquid amber, and many other rare plants in all their autumn splendour.

When: open until 26 May 2024
Where: Church Lane, Mount Wilson, NSW, Australia
More info on their website.

Have you got questions about Sydney in May? Pop over to our Facebook group and we would be happy to help.

Main Image Credit: Spinifex Group via Destination NSW