Revealed: the Illawarra's best gigs in May
Where to find the best live music in the month of May
While there’s an autumn chill in the air this month, our music scene is heating up.
Following a successful March 2025 festival weekend at Flagstaff Hill, Gong Christmas has been moved back to October this year – with a twist. An announcement this week said the Yours & Owls festival will return to Flagstaff Hill on October 3, with the line-up taking to the streets of Wollongong on October 4.
If October feels too far away, there’s plenty of gigs to tide you over in May.
Saturday Shoreys - Murray the DJ (The original Red Wiggle!)
Saturday May 2 | Coledale RSL | 5pm
Murray Cook is trading the big red car for the DJ decks at one of the Illawarra’s best-loved venues. Kicking off the Saturday Shoreys series, this is a perfect late-afternoon session for anyone holding onto 90s-2000s nostalgia or just looking for a fun, community vibe at the RSL.
Tickets: Free
Maddy Jane with GRXCE & Chelsea Daghita
Saturday May 2 | La La La's | 7pm
Catchy indie-pop with a fierce local following. Maddy Jane’s shows are known for being high-energy and community-driven. This is somewhat of a homecoming show, with Maddy having laid roots in Wollongong years ago, playing the Yours & Owls festival since she was 18. A perfect show to kick off the first weekend of May.
Guy Sebastian - 100 Times Around The Sun
Thursday May 7 | WIN Entertainment Centre | 7pm
Australia’s most enduring hitmaker returns to the Gong for his massive national tour celebrating his 10th studio album, 100 Times Around The Sun. Following the chart-topping success of his T.R.U.T.H. tour, fans can expect an evening of Guy's signature power vocals and a setlist packed with nostalgic hits such as Choir, Before I Go and Battle Scars alongside soul-filled new tracks.
MAY-A with special guests
Friday May 8 | La La La's | 7:30pm
One of the most exciting voices in Aussie indie-pop right now, MAY-A brings her raw songwriting and infectious energy to Globe Lane. Following a stellar performance at last year’s Yours & Owls festival, this will be a high-energy show that’s likely to sell out, so move fast. A perfect gig for those who like their pop a little grungey.
Sounds of Steel - Port Kembla Gig Trail (Great Southern Nights)
Saturday May 9 | Various Port Kembla venues | Various times
For the first time, Port Kembla will join Newcastle, Chippendale and Newtown as hosts of day-long, multi-venue gig trails organised by Great Southern Nights. Expect to see Wentworth St lined with live music, record label pop-ups, art exhibitions, and street performers. Go to this if you’re tickled pink by PK charm and live music in unexpected places.
Tickets: Free. RSVP
Tribute nights at Anita’s Theatre
Various dates | Anita's Theatre, Thirroul
The gem of Thirroul, Anita’s Theatre, is the go-to spot for big-production nostalgia this month. Catch The King of Pop Show (May 2) for a full-scale Michael Jackson experience, or travel back to the Rumours era with Seventh Wonder’s Fleetwood Mac tribute (May 16). On May 15, the From A Diamond To A King show will celebrate Neil Diamond and Elvis Presley, raising money to accelerate Parkinson’s research in Australia. On May 30, Letz Zep will perform their Led Zeppelin tribute. For something tender and moving, Lisa Simone delivers a daughter’s tribute to her mother, Nina Simone, on May 17.
Tickets via Anitas
Playlunch: The Sex Ed Tour
Sunday May 10 | University of Wollongong 6pm
Melbourne-sent bogan-funk heroes Playlunch bring their unique, tongue-in-cheek regional tour to town. Their album, Sex Ed, made a splash last August, featuring songs including Cool Math Games, Harold and Le Snak, intriguing and entertaining former year 6 students of a certain era. Nominated for two J Awards, including Australian music video of the year for their iconic single Keith, the band brings a blend of humor, high energy and synth-heavy indie-rock.
Running of the Bulls 2026
Saturday May 16 | La La La’s | 5pm
What started as a cheeky celebration of Taurus season for May-born friends of the venue has blossomed into a yearly mini-festival. This year, the high-energy line-up features CLAMM, Palms, and Private Wives, plus a stack of other loud local favourites. This is a must-attend for fans of loud guitars and the DIY spirit of the Gong's underground scene.
Keli Holiday
Friday May 29 | Uni bar | 8pm
The side-project of Peking Duk’s Adam Hyde, Keli Holiday is all about sweat-soaked, alt-rock-influenced pop. Go to this if you want to dance, have fun and enjoy hearing Triple J’s Hottest 100 winner live! Or if you really miss Michael Hutchence.
Richard Steele
May 21 and 22| La La La's & Coledale RSL | 7pm
A legendary blues homecoming. Richard Steele, a founding member of Wollongong’s own Whose Muddy Shoes returns from Tasmania for his first local show in decades.
Tickets: Free
Coming up in June
- City Tidda & The Sophia Rose Quartet (June 4): A sophisticated Music & Tea morning at the Wollongong Art Gallery.
- Molly Millington (June 5): Catch her Alma & More set for a dose of modern alt-country.
- Meg Mac (June 5): One of Australia’s powerhouse vocalists returns for a major show.
