Here's what's on the calendar for this month of May

If you’re wondering why it’s taken so long for us to punch out this monthly guide, I want you to continue to use those inside thoughts. Yes, I know it’s late. But I promise you, it’s for a damn good reason. There’s so much happening in Sydney this May that it quite literally made it impossible to choose what makes the hit list.

So, better late than never, right? Let’s go with that. This month in Sydney is honestly a cracker. It’s as if the nights start sooner, temperatures drop colder, and all of a sudden we decide to have some organised fun that might extend past 9pm. Sounds like a win, if you ask me.

Highlights include the return of Vivid, the Sydney Comedy Festival and Les Miserables, for those wanting to hit the big ticket items this May. But if you’re like me and would rather find some more off-the-beat-and-track kind of activities, you best believe I’ll be heading to Young Henry’s Rock & Roll Circus at Vic On The Park, as well as Red Bulls Symphonic with RUEL. Just to name a few.

In other words, you really are spoiled for choice this month ladies and gentlemen. So what are you waiting for? Whip those Google calendars out, transfer those bank funds, and get cracking, because here are the best things to do in Sydney this month of May.

Vivid Sydney

Image: Sydney, Australia

If hating Vivid was a full time sport, I’d be the reigning champion by now. Excessive crowds, overpriced chips on sticks and let’s be real, a rather sub par light show isn’t going to make me forget that Sydney after dark just isn’t where it is. BUT, I will caveat all of this in saying that admittedly, Vivid’s program kind of slaps this year. It’s as if the town has collectively realised that nightlife does get better when you add live gigs, free activities, and events that run past 9pm. We’ll be releasing our full lineup of favourites soon, so stay tuned for that.

WHEN: Friday 23 May to Saturday 14 June
WHERE: Across Sydney
HOW MUCH: Free (alongside ticketed events)
CHECK IT OUT HERE.

Sydney Comedy Festival

Image: Sydney Comedy Festival

Our favourite annual festival, the Sydney Comedy Festival, is back again to tickle all our funny bones. Having kicked off late last month, this year marks the festival’s largest program to date – with over 340 shows taking place across multiple venues including Enmore Theatre, Sydney Opera House and Bondi Pavilion. The festival will also be celebrating its 20th anniversary, so you can be guaranteed they’re going all out. And if you’re looking for our highlighted picks, best to head over here before booking your tickets.

WHEN: Monday 21 April to Sunday 18 May
WHERE: Multiple venues
HOW MUCH: Varies
CHECK IT OUT HERE.

Les Misérables

Image: The Rice Thresher

It’s our favourite and utterly dramatic musical, Les Misérables, and it’s back again on Sydney shores for the production’s 2025 world tour. Premiering Thursday 1 May, the show will run at the ICC Sydney Theatre for ten nights only, before heading to Melbourne. The musical, which has been seen by over 130 million people worldwide across 53 countries, is arguably one of the most iconic performances of all time. Matt Lucas and Marina Prior will be joining a star-studded cast, and believe it or not, but tickets are still available.

WHEN: Thursday 1 May to Sunday 11 May
WHERE: ICC Sydney Theatre, Darling Harbour
HOW MUCH: Tickets from $79
CHECK IT OUT HERE.

Chris Lake at Hordern Pavilion

Image: Hordern Pavilion

House music lovers are in for an absolute treat this month thanks to the return of Chris Lake, who will be performing at Hordern Pavilion this Saturday night. Whether he’s partnering with some of the biggest names in music rn (think FISHER, Sammy Virji, Solardo and Green Velvet) or releasing his own tracks, the British DJ has been a staple in the industry for longer than I can remember. Oh, and added bonus is that Noizu and Little Fritter will also be supporting. He’ll only be in Sydney for one-night and tickets are still available, so I suggest you jump on the bandwagon for this one asap.

WHEN: Saturday 10 May
WHERE: Hordern Pavilion, Moore Park
HOW MUCH: Tickets are $91
CHECK IT OUT HERE.

Soiree Cabaret at Paddington RSL

Image: TodayTix

Let’s be real, there’s nothing that quite beats a dinner and a show moment once the temperatures start to drop. And if you’re not the biggest musical fan, then not to fret – because we’ve got an equally entertaining option for you this month. Introducing Soiree Cabaret, the critically-acclaimed theatrical spectacular described as a “must-see sensation”. For one night only, you’ll be able to catch drag, burlesque, circus acts and vaudeville all in one show.

WHEN: Saturday 17 May, 7.30 – 10.30pm
WHERE: Paddington RSL, Paddington
HOW MUCH: Tickets from $69
CHECK IT OUT HERE.

Sydney Writer’s Festival

Image: Carriageworks

If you’re a BookTok fiend, then I’d say it’s the perfect time to get out and around some IRL action thanks to the Sydney Writer’s Festival that’s back again this month. Over the course of eight days, the city will be packed with workshops, panels and talks from a range of Australian and international writers. Highlights include Flawed Artists: The Minefield LIVE hosted by Waleed Aly and Scott Stephens, Gina Chick’s We Are the Stars talk, and Hannah Ferguson’s The F Word panel alongside Vanessa Turnbull-Roberts and Jess Hill.

WHEN: Monday 19 to Tuesday 27 May
WHERE: Across Sydney
HOW MUCH: Varies
CHECK IT OUT HERE.

Cassian at Roundhouse

Image: Mixmag Australia

Another music gig to be putting on your calendar this month, melodic techno guru Cassian will be performing at Roundhouse UNSW on Saturday 17 May. The Sydney-born DJ has collabed with the likes of Hayden James and done some seriously cool remixes of classics (like ICEHOUSE’s Great Southern Land or John Summit’s Shiver). Tickets are $70, and yes, there’s still some left.

WHEN: Saturday 17 May, from 7pm
WHERE: Roundhouse, UNSW
HOW MUCH: Tickets are $70
CHECK IT OUT HERE.

Launch of tqm.

Image: Supplied

If you’re one to frequent the Paddington area, you’d know by now that there’s nothing that quite beats a Tommy’s marg at Tequila Mockingbird. The Latin American institution has been slinging cocktails, tequila flights and epic food for nearly a decade. And while we hate to see the end of an era, the bar’s doors have recently closed to make way for something entirely new. Introducing tqm., launching this Thursday 8 May and entirely reimagining the previous establishment. Newly appointed Executive Chef Jose Garcia is bringing his Michelin-rated Venezuelan talent to the kitchen for what might just be the most exciting restaurant rebirth so far this year. This one’s definitely making the hit list.

WHEN: Open from Thursday 8 May
WHERE: tqm., Paddington
HOW MUCH: Varies
CHECK IT OUT HERE.

Young Henry’s Rock & Roll Circus

Vanda (Liquid Zoo) | Image: Supplied

Itching for live music this month? We know, it really can be a little hard to come by. But there’s no need to stress, because Vic On The Park is partnering with Young Henry’s this month to bring back their iconic Rock & Roll Circus event. Having originated in Frankie’s basement back in 2016, the Marrickville institution has been tasked with taking on the reigns in hosting a plethora of Aussie musos who’ll cover some of our favourite rock and roll covers. We’re especially excited for appearances by Harry O’Brien from Pacific Adventure, Father’s Favourite, and even a DJ set by Julian Hamilton from The Presets. Oh, and there’ll be comedy and drag shows, too.

WHEN: Friday 9 May, from 7pm
WHERE: Vic On The Park, Marrickville
HOW MUCH: Free entry
CHECK IT OUT HERE.

Taco and Tequila Fiesta at SoCal

Image: Supplied

Northsiders who are reluctant and unwilling to cross the bridge, it’s time you listen up. Iconic Mexican institution SoCal in Neutral Bay is treating us to yet another special running for the whole month of May, and it’s definitely worth the check out. Kicking off Saturday 3 May and running until the end of the month, they’re bringing back their Taco and Tequila Fiesta. Think launch parties, chilli eating contests and taco eating competitions alongside some pretty competitive weekly specials. Time to rally the girls, I say.

WHEN: Friday 3 May to Saturday 31 May
WHERE: SoCal, Neutral Bay
HOW MUCH: Varies
CHECK IT OUT HERE.

Pyrmont Festival

Image: Pyrmont Festival

Wine. Beer. Food. Art. Is there anything more, really? No. So it’s best you get your ass over to the Pyrmont Festival happening over the Saturday 17 and Sunday 18 May. Entry is free, and there’ll be 24 wineries alongside plenty of food vendors to gorge yourself from (including a pop-up oyster bar from the Sydney Fish Market). This is prime first date territory.

WHEN: Saturday 17 and Sunday 18 May
WHERE: Pirrama Park, Pyrmont
HOW MUCH: Free entry
CHECK IT OUT HERE.

Red Bull Symphonic ft. RUEL

Image: Supplied

It’s no secret that Red Bull hosts a cracking event, and this month marks no exception. For two nights this month, Red Bull Symphonic is returning to Sydney Town Hall alongside acclaimed Aussie artist RUEL for an unforgettable performance. The 22-year old artist will reimagine some of his greatest hits thanks to the help of Ensemble Apex, one of Australia’s leading orchestras for young musicians. Tickets are nearly sold out for this one so my advice is to get in quick.