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.

This page contains affiliate links. Please read our full disclosure policy for more details.

Major Annual Events in May

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

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

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.

Where: Carriageworks
When: 2024 dates TBC

Festivals and Community Events

Drag Expo Sydney

A celebration of Drag, Pop Culture & Beauty. The first-ever Sydney Drag Expo will take place over two days at the International Conference Centre (ICC) on the 19th-21st of May 2023, bring the whole family! Visitors to Drag Expo can meet the very best in Local & International Drag and Pop Culture superstars, see Australia’s legends and learn their inspiring stories, whilst enjoying a plethora of informative panels, tutorials, chill-out spaces, fabulous shopping, runways with Q&A sessions, meet and greets, official merchandise, a drag market and so much more.

Where: ICC Sydney 14 Darling Drive Sydney, NSW 2000 Australia
When: 20 – 21 May 2023 (Saturday 20 May at 10 am / Sunday 21 May at 4 pm)
Tickets: Visit their website for more info.

Twilight Penrith Festival

The festival brings together many local businesses, organisations, and groups along with a fantastic variety of food trucks and market stalls. This is a prime opportunity to showcase and grow awareness for all CBD businesses.

Where: High Street, Penrith
When: 19 May 2023 at 5 – 9 PM
Full guide here

Markets

Sydney Vegan Market

Get ready to feast on some of the BEST FOOD Sydney has to offer. It’s free entry and we’ve got LOADS of food and cruelty-free goodies! There’ll be live vegan artists at the main stage, free yoga, and face painting at the Art Space for $5!

Where: Cathy Freeman Park, Sydney Olympic Park
When: 21 May 2023 at 9am – 4pm

Boho Luxe Market – Sydney

Don’t miss this special opportunity to shop and explore a curated selection of over 125 artists, makers, and designers in Boho Luxe’s iconic bohemian setting.

Where: High Street, Penrith
When: 5- 7 May 2023
Tickets: Entry to the market is $5 (plus a booking fee) or $10 at the door. FREE entry for kids 12 & under. More details here

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.

Where: Woodstock Community Centre, 22 Church St, Burwood
When: TBC
Tickets: Free Entry. More details here

Musicals and Theatre

Comedy, Music, and Dance

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: TBC 2024
Where: Pirrama Park Pyrmont
Cost: Free.

Art & Exhibitions

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

When:
Where: 30 Balfour Street, Chippendale NSW
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: TBC
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

The Isuzu UTE A-League Finals Series continues this weekend with Sydney FC playing Melbourne City in the first leg of the semi-finals.

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 ‘Fast’ Ed Halmagyi.
• 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 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

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

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 and 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: 2024 dates to be confirmed.
Where: Church Lane, Mount Wilson, NSW, Australia

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