ISSUE 37. What’s on in Sydney this week: cult cinema, vintage markets and headline debuts

Fortunately for all of us, it appears that Sydney’s cultural calendar is doing nothing but speeding up, and we’re scoring yet another week of films, fringe performances, vintage fashion and very late nights ahead.

Honorary mention of the week go to the Sydney Underground Film Festival, returning to the Factory Theatre for its 20th anniversary. Across town, Second Life Markets are bringing over 120 vintage sellers to Carriageworks for all your retail therapy needs; and elsewhere, the Sydney Fringe continues its month-long campaign to make the city considerably weirder.

So, consider it time to clear some wardrobe space alongside the calendar. Here are the best things to do in Sydney this week.

HIGHLIGHTS

Sydney Underground Film Festival

Sydney Underground Film Festival is celebrating its 20th anniversary with four days of cult favourites, rebellious documentaries, boundary-pushing shorts and films unlikely to receive a commemorative popcorn bucket. Opening night features TURA!, a tribute to burlesque legend and cult cinema icon Tura Satana, while the festival closes with martial-arts revenge thriller The Furious.

• WHEN: Thursday 10 to Sunday 13 September
• WHERE: Factory Theatre, Marrickville
• HOW MUCH: Single screening tickets from $22
• CHECK IT OUT HERE.

Second Life Markets

Second Life Markets is returning to Carriageworks with over 120 vintage, designer and preloved fashion stalls from sellers across the country. There’ll also be DJs, food trucks, florals, baked goods and several opportunities to purchase an entirely new spring wardrobe that you definitely do not need.

• WHEN: Sunday 13 September, 9:30am to 4pm
• WHERE: Carriageworks
• HOW MUCH: Timed entry tickets from $6, free entry after 3:30pm
• CHECK IT OUT HERE.

Harry Hayes at Civic Underground

Sydney producer Harry Hayes is playing his first-ever headline show this weekend, taking over Civic Underground for an intimate hometown set. Having already landed releases on Ninja Tune’s Technicolour imprint, support from Fred again and Floating Points, and an official Caribou remix, he’ll move through house and UK garage tracks until the early hours.

• WHEN: Saturday 12 September, from 9pm
• WHERE: Civic Underground, CBD
• HOW MUCH: $33 final release tickets
• CHECK IT OUT HERE.

Sydney Fringe

Sydney Fringe is back for a month of comedy, cabaret, theatre, music, dance and performances that become increasingly difficult to explain to your colleagues the next morning. Over 350 shows are taking over theatres, pubs, warehouses and unexpected corners across the city, making September the ideal time to take a chance on something (or someone) you’ve never heard of.

• WHEN: All of September
• WHERE: Across Sydney
• HOW MUCH: Varies
• CHECK IT OUT HERE.

CLUB CHARLIE with Sammy Robinson

In the most Bondi thing to ever happen in Bondi, Chargrill Charlie’s are handing its store over to Sammy Robinson for a one-hour CLUB CHARLIE takeover. It’s all in celebration of their new limited-edition Signature Sammy Wrap, which you’ll be able to nab for free if you’re one of the first 100 people. Naturally, there’ll be live DJs and lucky-dip prizes also up for grabs.

• WHEN: Friday 11 September, from 11am to 12pm
• WHERE: Chargrill Charlie’s, Bondi
• HOW MUCH: Free
• CHECK IT OUT HERE.

FASHION & CULTURE

Free Perfume and Matcha at Cherry’s Goods

Recreation Beauty is celebrating its new Lucky Chaos fragrance by giving away free perfume and matcha at Cherry’s Goods. The first 100 people will receive a 12ml travel size fragrance and a caramel, peach, honey and milk matcha inspired by its notes. Let’s be real, it’s considerably more useful than being handed yet another tote bag.

• WHEN: Friday 11 September, from 9am
• WHERE: Cherry’s Goods at The Galeries, CBD
• HOW MUCH: Free for first 100 people
• CHECK IT OUT HERE.

Festival of the Winds

Festival of the Winds is returning to Bondi with enormous international kites, professional kite flyers, live music, cultural performances, workshops and food stalls. Up to 50,000 people are expected to attend, giving Bondi one rare Sunday where everyone is looking up rather than directly at themselves.

• WHEN: Sunday 13 September, from 10:30am
• WHERE: Bondi Beach
• HOW MUCH: Free
• CHECK IT OUT HERE.

Watsons Bay Spring Market

Watsons Bay Spring Market is bringing local fashion, homewares, food, art and live entertainment to Robertson Park for one particularly scenic Sunday of browsing. It’s the softer spring option for anyone who wants harbour views without entering the kite-based migration taking place over at Bondi.

• WHEN: Sunday 13 September, 9am to 3pm
• WHERE: Robertson Park, Watsons Bay
• HOW MUCH: Free entry
• CHECK IT OUT HERE.

COOEE Festival

Western Sydney’s major First Nations festival returns to Dharug Country for a full day celebrating Aboriginal and Torres Strait Islander culture. This year’s Voices of the Land program brings together live entertainment, cultural performances, Blak-owned businesses, market stalls, food and activities to keep you busy all afternoon.

• WHEN: Saturday 12 September, 10am to 6pm
• WHERE: Blacktown Showground
• HOW MUCH: Free entry
• CHECK IT OUT HERE.

FBi.Radio Presents: Unscripted

FBi Radio is taking over The Rocks Discovery Museum for a new Friday-night series pairing DJs with live storytelling and unscripted conversations about the city. This Friday night brings together TBindi Mutiara and Ifeoma (Ify) Obiegbu (plus the rare opportunity to visit a museum after dark).

• WHEN: Every Friday in September, 6-8pm
• WHERE: The Rocks Discovery Museum
• HOW MUCH: Free
• CHECK IT OUT HERE.

MCA Late

Thursday night culture is sorted, with the MCA staying open until 9pm for an after-dark mix of contemporary art, drinks, harbour views and rotating talks, performances and creative experiences. This week’s admission also covers Primavera 2026, Connections: MCA x Tate and the major Tony Albert exhibition. Even better is that tickets are two-for-one.

• WHEN: Every Thursday, 5-9pm
• WHERE: Museum of Contemporary Art, The Rocks
• HOW MUCH: 2-for-1 tickets from $20
• CHECK IT OUT HERE.

Connections: MCA x Tate

The MCA has joined forces with Tate for a major new exhibition bringing together works acquired through the two institutions’ international joint collection. Featuring works by 24 Australian artists, the exhibition explores cultural exchange, migration, colonisation and First Nations histories, with several new commissions created specifically for the Sydney exhibition. It’s on now at the MCA until early next year, so you’ve got plenty of time to pretend this is the week you become someone who regularly goes to galleries.

• WHEN: Until Monday 1 March 2027
• WHERE: Museum of Contemporary Art, The Rocks
• HOW MUCH: $25 adult tickets
• CHECK IT OUT HERE.

Definitive Dupain at State Library of NSW

A major new Max Dupain retrospective at the State Library of NSW brings together almost 200 iconic, rare and previously unseen photographs from across his 60-year career. Definitive Dupain spans everything from Sunbaker and experimental photography to unseen images of the Sydney Opera House under construction, fashion, architecture and candid personal work, all pulled from an archive of around 250,000 negatives. Best part: it’s completely free.

• WHEN: Until July 2027
• WHERE: NSW State Library
• HOW MUCH: Free
• CHECK IT OUT HERE.

Cedar & Salt Sauna at Barangaroo

Barangaroo has somehow found a way to make sweating in public feel chic. Cedar & Salt has brought its Nordic-style sauna back to Marrinawi Cove for winter, meaning you can spend an hour moving between a steaming timber sauna and an extremely character-building dip in Sydney Harbour. Sessions run in communal groups of up to 12, with harbour views included and the recommended routine being heat, cold plunge, repeat until you’ve convinced yourself you’re basically Scandinavian.

• WHEN: Until end of September
• WHERE: Marrinawi Cove, Barangaroo
• HOW MUCH: From $30 per single session
• CHECK IT OUT HERE.

Black Myth at White Rabbit Gallery

Our favourite Sydney art gallery is officially back in action with its newest exhibition, Black Myth. Drawing from the wildly successful video game, the exhibition explores how ancient mythology can still tell us things about the modern world. Inspired by Journey to the West, Black Myth brings together artists including Sun Xun, Zong Ning and Hou Chun-Ming to explore transformation, transcendence and the darker side of myth through woodcuts, ink painting, photography and plenty of strange, otherworldly figures.

• WHEN: Until Sunday 15 November
• WHERE: White Rabbit Gallery, Chippendale
• HOW MUCH: Free entry
• CHECK IT OUT HERE.

MUSIC & NIGHTLIFE

Gallery Pres: O’Flynn at Oxford Art Factory

UK producer O’Flynn is making his long-awaited Australian debut with an all-night trip through house, disco and considerably heavier club territory. With releases across Ninja Tune, collaborations with Bonobo and Barry Can’t Swim, and support from Four Tet and Ben UFO, this is a fairly major booking for the weekend.

• WHEN: Friday 11 September, from 11pm
• WHERE: Oxford Art Factory, Darlinghurst
• HOW MUCH: $50 final release tickets
• CHECK IT OUT HERE.

Jazz Sessions in The Rocks

Jazz Sessions are back again for August, transforming The Rocks Square into a free open-air jazz spot every Thursday night. Curated in collaboration with the Sydney Improvised Music Association, the lineup remains mixed, the pizza remains $10, and the pop-up bar remains pouring mulled wine. Consider this your new go-to date night idea.

• WHEN: Every Thursday night, 6:30-8:30pm
• WHERE: The Rocks Square
• HOW MUCH: Free
• CHECK IT OUT HERE.

FOOD & DRINK

Sydney Sake Festival

Sydney Sake Festival is taking over the Overseas Passenger Terminal with over 400 varieties to taste at your own risk. There’ll be visiting brewers from Japan, seminars, cultural experiences, plenty of Japanese food and a festival cup to take home. Enjoy maintaining detailed tasting notes by sake number 37.

• WHEN: Friday 11 to Sunday 13 September
• WHERE: Overseas Passenger Terminal, The Rocks
• HOW MUCH: $79 general admission tickets
• CHECK IT OUT HERE.

$10 Steak and Chips at The Duke of Enmore

The Duke of Enmore is serving steak and chips for $10 every Tuesday with the purchase of a glass of VB. It’s a complete pub dinner for less than the price of most Sydney cocktails, provided you are willing to accept that VB is now technically part of the meal.

• WHEN: Every Tuesday in September
• WHERE: The Duke of Enmore, Enmore
• HOW MUCH: $10 with purchase of VB
• CHECK IT OUT HERE.

Jude’s DIY Martini Menu

New Potts Point cocktail bar Jude’s has launched a DIY martini menu featuring seven vodkas, seven gins and a sliding scale from dry to dirty. Finish it with lemon, submerged pickles or an eight-olive stack for a drink that arrives with enough garnish to qualify as a light dinner.

• WHEN: Thursdays to Saturdays, 5pm until late
• WHERE: Jude’s, Potts Point
• HOW MUCH: Martinis from $22
• CHECK IT OUT HERE.

Quips x Cabana Thursdays

Thursday knock-offs just got dangerously affordable thanks to Quips x Cabana Thursdays. Come 4pm each night, you’ll be able to score a margherita pizza and four Tommy’s Margarita pouches for just $50. Alternatively, you can also nab four cocktail pouches for $40 until 7pm.

• WHEN: Every Thursday, 4-7pm
• WHERE: Cabana Bar, Martin Place
• HOW MUCH: $10 per marg
• CHECK IT OUT HERE.

Suntory House Takeover

Suntory House is returning to Sydney for its third rendition, taking over Sakura House in the CBD until early October. Inspired by Japan’s nomikai tradition of post-work drinking, the limited-time residency will serve highballs, sours, beer on tap and bespoke cocktails like the ‘Mazda Zoom Zoom’ melon float. Of course, it comes alongside all the elevated izakaya snacks Sakura House has become well-known for.

• WHEN: Friday 31 July to Saturday 3 October
• WHERE: Sakura House, Martin Place
• HOW MUCH: Free entry
• CHECK IT OUT HERE.

Island Radio Bottomless Yum Cha

As Sydneysiders, we’re almost all well-versed by now in the weekend bottomless brunch session. But bottomless yum cha, however, is something that we hadn’t tried until now. Introducing Island Radio’s bottomless Dim Sum Saturdays, which serves up the likes of dumplings, steamed buns, wagyu nigiri and other yum cha classics alongside 90 minutes of bottomless booze for $90 a head. Honestly, after trying it for ourselves recently this one has instantly shot up to the top of our list.

• WHEN: Every Saturday and Sunday
• WHERE: Island Radio, Redfern
• HOW MUCH: $90 per person
• CHECK IT OUT HERE.

Oyster Happy Hour at Morrison’s

I see no reason why the cost of living should get in the way of good taste, and neither does Morrison’s. If you didn’t already know, they’re kind of the go-to place for happy hour oysters in town. In fact, they sell a minimum of 6,000 oysters every week. Every Wednesday from 6-7pm, you’ll be able to snag those little gems for $2 each, which is kind of insane. Or if you want to check out the other oyster happy hours currently happening around town, head over here.

• WHEN: Every Wednesday, 6pm to 7pm
• WHERE: Morrison’s Oyster Bar & Grill, CBD
• HOW MUCH: $2 per oyster
• CHECK IT OUT HERE.