Best Things to Do in Sydney This May | What’s On May In Sydney

18 hours ago
8 min read

Updated: 4 hours ago

May in Sydney leans into long lunches, design markets and late nights, with the city shifting into a busier, more social rhythm. The days are cooler, the nights stretch a little longer, and there’s more reason to stay out.

From fashion-led markets and chef takeovers to one-off pop-ups and cultural festivals, this month’s line-up covers the lot.

Here’s your guide to what’s on.

The best things to do in Sydney May

Meatstock Sydney 2026

Sydney Olympic Park | Friday 1 May – Saturday 2 May

Meatstock returns to Sydney Showground for two days of live music, barbecue and high-energy competition. The program spans pitmaster battles, butcher showdowns and bull riding, alongside a full music lineup across both days. Expect plenty of food, drinks and crowd-driven entertainment, from eating contests to strength events. It’s a loud, full-scale festival built around barbecue culture.

When: Friday 1–Saturday 2 May 2026

Where: Sydney Showground, Sydney Olympic Park

Price: From $65.50

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Texas BBQ: Pitmasters at Firedoor

Surry Hills | Friday 1 May – Monday 4 May

Firedoor hosts a limited BBQ takeover this May, bringing Austin pitmaster Kareem “KG” El-Ghayesh to Sydney for the first time. Known for blending Texas smoking with Egyptian flavours, KG joins Lennox Hastie for a series of dinners, live fire sessions and masterclasses. Expect brisket-led menus alongside music and a more hands-on format across the weekend

When: 1–4 May 2026

Where: Firedoor, Surry Hills

Price: Ticketed

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The Finders Keepers Sydney Design Market AW26

Eveleigh | Friday 1 May – Sunday 3 May

The Finders Keepers returns to Carriageworks with over 150 designers and makers showcasing independent fashion, homewares and small-batch goods. It’s a go-to for one-off pieces and limited runs, with stalls that tend to sell out across the weekend. Alongside the shopping, expect food, drinks and a steady crowd of design-focused locals. It’s well timed ahead of Mother’s Day if you’re after something less obvious.

When: 1–3 May 2026

Where: Carriageworks, Eveleigh

Price: From $7

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William Street Social

Paddington | Saturday 2 May

William Street Social takes over Paddington for a one-day street activation centred on local music, retail and creative pop-ups. Boutiques and venues along the strip will host DJs, installations and in-store experiences throughout the day. Expect limited releases, food and drinks, and a strong lineup of local brands and designers.

When: Saturday 2 May, various times

Where: William Street, Paddington

Price: Free

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La Lune Creative Markets

Sydney | Saturday 2 May & Saturday 9 May

La Lune hosts two weekends of creative markets, bringing together small brands, artists and live music. The lineup includes jewellery, florals, handmade goods and pop-ups, with workshops and live portrait drawing on select dates. DJs and acoustic sets run across both Saturdays, alongside coffee and food from the café. A portion of coffee sales will be donated to World Vision.

When: Saturday 2 May & Saturday 9 May, markets 9am–2pm

Where: La Lune, Sydney

Price: Free entry

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To Be Read Book Club

Surry Hills | Sunday 3 May

To Be Read Book Club returns to Beta Coffee for an afternoon of discussion centred around Sally Hepworth’s latest novel. The session is open to everyone, whether you’ve finished the book or just started, with guided prompts to keep the conversation flowing. Expect a relaxed setting with coffee, snacks and a room of fellow readers. It’s an easy way to meet people and spend a slower Sunday afternoon.

When: Sunday 3 May 2026, 4pm–6pm

Where: Beta Coffee, Surry Hills

Price: Ticketed

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Milk Bar Takeover at Good Chemistry

Surry Hills | Friday 1 May – Sunday 3 May

Milk Bar lands at Ace Hotel this May, with Christina Tosi taking over laneway café Good Chemistry for a limited run. The pop-up brings a taste of New York, with cult favourites like Cereal Milk soft serve and signature cookies on the menu. A one-off dessert, created in collaboration with Ace Hotel’s culinary team, will also be available across the weekend. Expect lines early, with items selling out each day.

When: 1–3 May 2026, 8am–2pm

Where: Good Chemistry, Ace Hotel Sydney, Surry Hills

Price: Menu priced

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Second Life Markets – Evening & Bridal Pop-Up

Paddington | Friday 8 May – Sunday 10 May

Second Life Markets brings a two-day pop-up to Oxford Street, centred on vintage evening and bridal pieces. Expect a curated mix of formalwear, accessories and jewellery sourced from collectors, with a focus on one-off finds. It’s a strong option if you’re dressing for an event or after something less expected. Drop in across the weekend to browse the full selection.

When: 8–10 May 2026

Where: 207 Oxford Street, Paddington

Price: Free entry

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Huge Moves 11 with DRNKs

Surry Hills | Saturday 9 May

Huge Moves returns to Ace Hotel for its eleventh edition, bringing together over 30 winemakers and importers for a one-session tasting. Expect more than 100 pours, alongside beers, cocktails and food running throughout the afternoon. DJs will carry the room, with a crowd that knows exactly what they’re there for. It’s less a formal tasting and more a loose, high-energy wine party.

When: Saturday 9 May 2026, 1pm–4pm

Where: Ace Hotel Sydney, Surry Hills

Price: $60

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Club Matcha: Matcha Cereal Bar Pop-Up

Darlinghurst | Saturday 9 May

Club Matcha is hosting a one-day cereal-themed pop-up at Nomidokoro Indigo, centred around playful matcha drinks and build-your-own bowls. Expect flavours inspired by classic cereals, alongside a menu that leans sweet and nostalgic. It’s a short morning session, with limited hours and likely early sell-outs.

When: Saturday 9 May, 9am–1:30pm

Where: Nomidokoro Indigo, Darlinghurst

Price: Menu priced

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B*tches & Stitches: Beaded Embroidery Workshop

Watsons Bay | Saturday 16 May – Sunday 17 May

This beaded embroidery workshop at Loja brings a hands-on session focused on customising your own clothing piece. Guided by Naru Studios, the class covers the basics with stencils and materials provided, making it accessible for beginners. Each ticket includes a drink on arrival and a relaxed setup designed for small groups. It’s a social, creative way to spend an afternoon by the water.

When: 16–17 May 2026

Where: Loja Watsons Bay, 21 Military Rd, Watsons Bay

Price: $95

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Sydney Writers’ Festival

Eveleigh | Tuesday 19 May – Sunday 24 May

Sydney Writers’ Festival returns to Carriageworks with a multi-day program of talks, panels and live conversations. Writers, journalists and thinkers come together for discussions spanning books, culture and current ideas. The precinct shifts into a meeting point for readers and creatives across the week. Expect a mix of headline sessions and smaller, in-depth conversations.

When: 19–24 May 2026

Where: Carriageworks, Eveleigh

Price: Free and ticketed events

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Club Sup Supper Club

Darlinghurst | Thursday 21 May

Club Sup hosts an intimate supper club at Fabbrica, bringing together a small group for a shared dining experience. The evening begins with drinks and standing conversation before moving into a three-course Italian menu with wine pairing. With limited seats, the format is designed to make meeting new people feel natural. It’s a structured but relaxed take on dinner and socialising.

When: Thursday 21 May 2026, 6:30pm–9:30pm

Where: Fabbrica Pasta Bar, Darlinghurst

Price: Ticketed

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MODA Designer Sydney AW26

Rozelle | Saturday 23 May

MODA returns with its AW26 showcase, taking over White Bay Cruise Terminal for a night of emerging fashion, music and culture. Ten independent designers will present new collections across a continuous runway format, set within a standing crowd and soundtracked by live DJs. The space shifts between show and dance floor, with pieces available to buy directly from the designers on the night. It’s a more open, immersive take on the traditional runway.

When: Saturday 23 May 2026, from 5:30pm

Where: White Bay Cruise Terminal, Rozelle

Price: Ticketed

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Paddington Markets Ceramics Pop-Up

Paddington | Saturday 23 May

Paddington Markets is hosting a dedicated ceramics pop-up, bringing together local makers for a one-day event focused on handmade pieces. Expect a mix of functional ceramics and one-off designs, with a strong emphasis on slow, small-batch production. It’s a more focused edit of the usual market, centred on craft and material.

When: Saturday 23 May, 10am–4pm

Where: Paddington Markets, Paddington

Price: Free entry

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Pyrmont Food and Wine Festival

Pyrmont | Saturday 23 May – Sunday 24 May

The Pyrmont Festival returns to Pirrama Park for a two-day celebration of food, wine and local makers. Wineries from across NSW join breweries, distilleries and food trucks, with live music running throughout the day. There’s also a mix of art activities, workshops and a dedicated kids zone. It’s an easy, all-day event by the water with a strong community feel.

When: 23–24 May 2026, 11am–5pm

Where: Pirrama Park, Pyrmont

Price: Free entry

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Cronulla Jazz & Blues Festival 2026

Cronulla | Wednesday 27 May – Sunday 31 May

Cronulla Jazz & Blues Festival returns with five days of live music, taking over the suburb with more than 200 free performances across multiple stages. The program spans jazz, blues, soul and funk, alongside a lineup of ticketed shows, markets and community events. Expect bars, food stalls and a full weekend atmosphere by the beach. It’s one of the few large-scale music festivals in Sydney that remains largely free.

When: 27–31 May 2026

Where: Cronulla

Price: Free and ticketed events

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Second Life Archive Market

Sydney CBD | Saturday 30 May

Second Life Archive returns to Machine Hall with a curated edit of archival fashion, bringing together rare designer pieces and hard-to-find one-offs. The market leans more premium than typical vintage, with a focus on quality, collectability and sustainable shopping. Live auctions will run throughout the day, offering access to select pieces in real time. Expect a strong crowd early, with staggered entry across the day.

When: Saturday 30 May 2026, 10:30am–4pm

Where: Machine Hall, 185 Clarence St, Sydney

Price: From $6, free from 3:30pm

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25th Biennale of Sydney

Rozelle | Until 14 June

The Biennale of Sydney takes over White Bay Power Station with a large-scale contemporary art program exploring themes of memory, identity and storytelling. The exhibition brings together international artists across installations, performances and moving image works within the industrial space. Alongside the main program, expect guided tours, weekend food markets and Friday night Art After Dark sessions.

When: Until 14 June, Tuesday–Sunday

Where: White Bay Power Station, Rozelle

Price: Free (some ticketed events)

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Tarot & ’Tinis

Sydney | First & Third Tuesday of Every Month

Find out what’s next, martini in hand. Tarot & ’Tinis pairs one-on-one readings with $12 miniature Martinis — Gin, Espresso or French — poured cold while the cards are laid on the table. It runs from 7–9pm on the first and third Tuesday of each month, with bookings essential and no walk-ins.

When: First & Third Tuesday of every month, 7pm–9pm

Where: Sydney (see booking link for details)

Price: $12 mini Martinis

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Carriageworks Farmers Market

Eveleigh | Every Saturday

Carriageworks Farmers Markets are one of the most iconic markets in Sydney. In addition to seasonal fruits and vegetables, you'll find fresh flowers, artisanal coffee, amazing makers as well as delicious eats for you to enjoy there from AP Bakery or Broomfields.

When: Every Saturday, 8am - 1pm

Where: 245 Wilson St, Eveleigh

Price: Free

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Glebe Markets

Glebe | Every Saturday

Glebe Markets is a Sydney institution, known for its mix of vintage fashion, independent designers and handmade finds. You will find everything from jewellery and local labels to one-off pieces worth digging for. Enjoy food from a range of food trucks through to local baked goods, with space to picnic on the lawn alongside other market-goers.

When: Every Saturday 10 10am - 4pm

Where: Derby Place, Glebe Point Rd, Glebe

Price: Free entry

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