Best Things to Do in Sydney This May | What’s On
- Smashd Sydney
- Apr 30
- 7 min read
Updated: Jun 3
Sydney in May is bringing mix of culture, design, food and music. From archive fashion sales and vinyl fairs to pop-up matcha bars, chef collaborations and the return of Vivid, it’s a month that blends headline events with low-key highlights.
Whether you’re planning ahead or just looking for something new, here’s our guide to the best things to do in Sydney this May.
Best Things to Do in Sydney This May:
The Finders Keepers Sydney Design Market
Eveleigh | Friday 2 – Sunday 4 May
The Finders Keepers Sydney Design Market returns to Carriageworks this May, bringing together over 200 designers, makers and food vendors across an expanded market floor. Browse ceramics, homewares, art, fashion and more, with live DJs and fresh food on hand. Perfect for picking up something special ahead of Mother’s Day — or just spending the weekend browsing one-of-a-kind finds.
When: Friday 2 May – Sunday 4 May
Where: Carriageworks, Eveleigh (Gadigal Land)
Price: From $8 early bird, $12 at the door (kids under 13 free)
More Info Here
Chinatown Country Club Archive Event
Sydney CBD | Friday 2 – Sunday 4 May
Chinatown Country Club is opening the archives for three days only, think vintage COMME des GARÇONS, Yohji Yamamoto, Issey Miyake, Maison Margiela and more, all handpicked by CCC’s expert buying team. Alongside rare pieces from Japan and France, you’ll also find selects from cult Melbourne labels like Aphidmarket and Garb.
When: Friday 2 – Sunday 4 May
Where: Chinatown Country Club, 222 Clarence Street, Sydney CBD
Price: Free entry
More Info Here
Coravin World Wine Tour at Love, Tilly Devine
Darlinghurst | Thursday 1 – Saturday 31 May
For one month only, every bottle on the list at Love, Tilly Devine is available by the glass, no corkscrew required. As part of the Coravin World Wine Tour, this laneway favourite is unlocking 300+ bottles, from Staffelter Hof’s ancient skin-contact wines to rare picks by Patrick Sullivan and Poppelvej.
It’s a rare chance to taste your way through the cellar, one glass at a time.
When: Thursday 1 May – Saturday 31 May
Where: Love, Tilly Devine, 91 Crown Lane, Darlinghurst
Price: By the glass (menu pricing)
More Info Here
HOKA Runaway Sydney Half Marathon
Sydney CBD | Sunday 4 May
For one morning only, Sydney’s streets are yours. The HOKA Runaway Half Marathon returns with over 15,000 runners taking on a 21.1km course through the city — from the Harbour Bridge to The Rocks and beyond. It’s Australia’s biggest half-marathon, with big views and even bigger energy.
When: Sunday 4 May
Where: Cahill Expressway & Sydney CBD
Price: $195 per person
More Info Here
The Whisky Show Sydney
The Rocks | Saturday 3 May
Australia’s leading whisky tasting event returns, bringing over 100 whiskies from around the world to The Rocks for one day only. Explore global and local favourites, discover new releases, and sip your way through a four-hour session with live music, food trucks, and a take-home tasting glass.
When: Saturday 3 May (two sessions) Where: 130 Argyle Street, The Rocks Price: $145 per person, Includes tastings + $20 food voucher (see site for tickets) More Info Here
Rozelle Vinyl Record Fair
Rozelle | Saturday 3 May
Dig through crates of classics, rarities and fresh finds at the Rozelle Vinyl Record Fair. Expect thousands of records, retro collectibles, posters and music memorabilia, plus live DJ sets and international food stalls.
When: Saturday 3 May, 9:00am – 3:00pm
Where: Rozelle Public School, 663 Darling St, Rozelle
Price: Free entry
More Info Here
Hats for Homeless Workshop
Paddington | Saturday 3 May
Spend a Saturday doing good at the Hats for Homeless workshop at Paddington Uniting Church, where volunteers will loom beanies for people sleeping rough. Whether you’re a seasoned crafter or a complete beginner, looms, wool and guidance are all provided. With over 17,000 handmade hats already donated, it’s a fun way to lend your hands to a great cause.
When: Saturday 3 May, 10:00am – 12:00pm
Where: Paddington Uniting Church, Paddington
Price: Donation basis
More Info Here
The Art of Movement: Van Cleef & Arpels
The Rocks | Until Thursday 8 May
Van Cleef & Arpels brings The Art of Movement to Sydney, showcasing over 100 High Jewellery creations and 50 archival documents at Watersedge, Campbell’s Stores. Spanning themes from Human Odyssey and Nature Alive to Elegance and Abstract Movements, the exhibition explores how the Maison captures motion in precious materials. Entry is free, with guided tours and workshops available by reservation.
When: Friday 11 April – Thursday 8 May, 10:00am – 6:00pm (last entry 5:15pm)
Where: Watersedge at Campbell’s Stores, 25 Hickson Rd, The Rocks
Price: Free entry (guided tours and workshops by booking)
More Info Here
Maple Social Club: Sunday Jazz
Paddington | Sunday 4 May
Wind down your weekend with a Sunday arvo session of live jazz, drinks, and easy company. Hosted by Maple Social Club in collaboration with Lord Dudley Live, the music starts at 4:30pm and carries through the evening. With limited spots and RSVP-only entry, it’s the kind of Sunday worth planning for.
When: Sunday 4 May, 4:30pm – 7:00pm
Where: Paddington (RSVP for full location)
Price: Free with RSVP
More Info Here
Experience Animal Crossing: New Horizons
Darling Harbour | Until Sunday 18 May
SEA LIFE Sydney is turning island mode on with an Animal Crossing takeover. Wander through the aquarium, collect character stamps, learn fun marine facts, and meet Isabelle IRL. A sweet crossover for fans of the game, and a fun excuse to visit the underwater world.
When: Monday 28 April – Sunday 18 May
Where: SEA LIFE Sydney, 1–5 Wheat Road, Darling Harbour
Price: Included with general admission
More Info Here
Second Life Archive: Sydney 2 Day Event
Sydney CBD | Saturday 10 – Sunday 11 May
Second Life is back, taking over Machine Hall for two days of high-quality archive hunting. There will be 25 sellers from across Australia and South East Asia, plus rare finds in fashion, furniture, books and more. VIP early bird tickets are limited, or hit the last hour on Sunday for free.
When: Saturday 10 May, 11:30am – 6:00pm; Sunday 11 May, 11:00am – 5:00pm
Where: Machine Hall, 185 Clarence Street, Sydney CBD
Price: From $10; free entry Sunday 4–5pm
More Info Here
Club Matcha Pop-Up at Momo Art Mart
Town Hall | Saturday 17 – Sunday 18 May
Club Matcha is popping up at Momo Art Mart with a new Peach Beach collection of matcha drinks, sweet treats and limited-edition merch. Following a string of sell-out appearances, the cult favourite brings a coastal-inspired lineup to Town Hall for one weekend only.
When: Saturday 17 – Sunday 18 May, 10:00am – 3:00pm
Where: Momo Art Mart, Town Hall
Price: Free entry (items available for purchase)
More Info Here
Vivid Sydney 2025
Across Sydney | Friday 24 May – Saturday 15 June
Vivid is back, bigger, brighter and this time, it's mostly free. This year’s festival reimagines Sydney across five immersive zones, from Circular Quay to the Inner City, with light installations, live music, food pop-ups and talks all centred on the theme dream.
Don’t miss the Light Walk (which is finally free again!), or check out free gigs at Tumbalong Park, dinners with Nigella, talks at Carriageworks and beyond.
When: Friday 24 May – Saturday 15 June
Where: Across Sydney (Circular Quay, The Rocks, Barangaroo, Darling Harbour & more)
Price: 75% of the program is free
More Info Here
Urban Wine Walk: Bondi
Bondi | Saturday 24 May
Swap the vineyard for the coastline, Urban Wine Walk is back, turning Bondi’s favourite spots into pop-up cellar doors for the day. Enjoy tastings from top winemakers, a glass of Prosecco on arrival, and an afternoon wandering between venues like Ravesis, Salty’s and Chloe’s.
You’ll get wine, snacks, a tasting glass to keep, and maybe a new favourite drop along the way. It’s self-guided, so you can choose your own route, no booking shuffle required.When: Saturday 24 May, 12:00pm – 4:00pm
Where: Multiple venues, Bondi
Price: $82 (includes tastings, food & wine vouchers, glass)
More Info Here
GABS Craft Beer Fest
Darling Harbour | Friday 30 – Saturday 31 May
GABS is back, and yes, the 120-tap bar is real. Over two days at ICC Sydney, you’ll sample beers you won’t find anywhere else: sushi IPAs, cookie stouts, lollipop sours and more, straight from 60+ local and international brewers. Add in cocktails, live music, sideshow acts and a silent disco, and this is far from your average beer fest.
When: Friday 30 – Saturday 31 May
Where: ICC Sydney, 14 Darling Drive, Darling Harbour
Price: $49 per person
More Info Here
Ester x James Lowe | Vivid Chef Series
Chippendale | Tuesday 27 – Thursday 29 May
For three nights only, London’s James Lowe (Lyle’s) joins Mat Lindsay at Ester for a one-off menu celebrating the best of NSW produce. Expect a meeting of two of the sharpest minds in wood-fired, ingredient-led cooking, set inside one of Sydney’s most loved dining rooms. It’s a rare collaboration, and one of Vivid’s hottest tickets.
When: Tuesday 27 – Thursday 29 May
Where: Ester, 46–52 Meagher St, Chippendale
Price: From $250
More Info Here
Hollywood Dreaming | A Taste of HQ
Surry Hills | Saturday 31 May
Foster Street in Surry Hills will transform into a vibrant open-air dining precinct for one night only during Vivid Sydney's Hollywood Dreaming. A Taste of HQ brings exclusive dishes, small plates and festival specials from Sydney favourites like Firedoor, Kiln, and Chin Chin, alongside live music and roving performers. The Hollywood Hotel will keep the energy high with entertainment spilling onto the street all night. Expect a buzzing celebration of food, music, and community right in the heart of the Hollywood Quarter.
When: Saturday 31 May, 5:00 pm – 11:00 pm
Where: Hollywood Quarter – Foster St, Surry Hills
Price: Free entry (food and drinks available for purchase)
More Info Here
Jazz Sessions in The Rocks
The Rocks | Every Thursday
Jazz Sessions is back — bringing smooth sounds, good drinks and local talent to The Rocks every Thursday night. Catch two live sets under the lights at The Rocks Square (or indoors nearby if it rains), with cocktails from Hickson House and a rotating lineup of homegrown jazz acts curated by SIMA. It’s free, weekly, and a solid excuse to linger after work.
When: Every Thursday, 6:00pm – 8:30pm
Where: The Rocks Square, Playfair Street, The Rocks (or 6–8 Atherden St in wet weather)
Price: Free
More Info Here
Now, go have some fun..
Best Things to Do in Sydney This May
Whether you're after festivals, street parties, intimate dinners, or creative workshops, these curated events in Sydney have something for every vibe.
Follow Smash'd Syd for more curated guides, and if you’ve got an event coming up, send it in—I’m always on the lookout for what’s on in Sydney.
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