Some of the Illawarra’s youngest triple threats are here to inspire in Newsies Jr. Photo: Michael Bond Photography.
From the high-energy stomping grounds of Dapto’s newest country music festival to the delicious aroma of roasting chestnuts in Fairy Meadow, the Illawarra is serving up a massive calendar of entertainment this week.
If you’ve been feeling the itch to shop, you’re in luck, with a massive designer fashion haul landing in Warrawong, while those who prefer a side of satire with their weekend can catch a certain former premier singing her heart out on stage.
Whether you’re cheering for precocious paperboys in a high-stakes musical or exploring the “wicked” history of our coastal city, this week is all about community spirit and big-stage energy.
Let’s dive into the best of the region.
Multiple Days
Extra! Extra! Read all about it! The talented youngsters of the Arcadians Children’s Theatre are bringing the gritty streets of New York to Corrimal. Image: Arcadians Theatre Group.
Newsies JR.
When: Until Sunday 3 May, various times
Where: The Miner’s Lamp Theatre, 141 Princes Highway, Corrimal
Cost: Adult $30 | Senior/Youth $20 | Child $18 | Book via Try Booking.
Based on the real-life Newsboys Strike of 1899, this high-energy production of Disney’s Newsies JR is packed with non-stop choreography and heart-pumping anthems. These kids have already picked up awards for their passion and with tickets selling faster than a morning edition, you’ll need to “seize the day” to catch the final performances. It’s an inspiring tale of underdog spirit that will have the whole family cheering in their seats.
Fashionistas, start your engines. Image: Dress for Success.
Super Fashion Frenzy
When: Saturday 2 May, noon to 2 pm (VIP), 2 to 5 pm (General) and Sunday 3 May, 10 am to 2 pm (Finisher)
Where: Illawarra Yacht Club, 1 Northcliffe Drive, Warrawong
Cost: Saturday VIP $50 | Saturday General $20 | Sunday Finisher $10 | Book via Humanitix.
The Super Fashion Frenzy returns with thousands of preloved and new designer pieces from the likes of Zimmermann, Coach, and Louis Vuitton. Whether you’re chasing a VIP experience with bubbles and first dibs or hunting for $5 steals during the Sunday “Frenzy Finisher,” there is a bargain here for every budget. Best of all, your shopping spree serves a greater purpose, with all proceeds supporting Dress for Success Illawarra to empower local women entering the workforce. Remember to bring your own bags — you’re going to need them for this massive wardrobe overhaul.
Friday
Gladys: A Musical Affair
When: Friday 1 May, 7:30 pm
Where: IMB Theatre, IPAC, 32 Burelli Street, Wollongong
Cost: $50 Adult | $45 Concession/Group/U30 | Book via TicketSearch.
She’s back, she’s bold, and she’s definitely not resigning from the spotlight. The satirical sensation that took the internet by storm during the lockdown era has been transformed into a full-scale musical comedy. Follow the rise and dramatic “Dodgy Daryl” related hurdles of Gladys Berejiklian in a production that features everything from Armenian matchmaking to tap-dancing press conferences. With a wardrobe full of colourful blazers and a score featuring big rock numbers and epic ballads, this sharp-witted show proves that local politics is the perfect fodder for a night of musical mayhem.
Kick off the weekend with a dose of soul-drenched vocals and gritty guitar riffs as Mick on Wheels takes over the stage at Club Jamberoo. Image: Club Jamberoo.
Mick on Wheels Live
When: Friday 1 May, 6 pm
Where: Club Jamberoo, 11 Allowrie Street, Jamberoo
Cost: Free.
A veteran of the Australian blues scene, local legend Mick on Wheels brings over a decade of touring experience to this intimate performance. Expect a dynamic blend of heartfelt original tracks and high-impact covers that bridge the gap between blues, rock and soul. Whether you choose to settle in the cozy indoor lounge or enjoy the breeze on the verandah, it’s the ultimate way to unwind with a cold drink and some world-class musicianship in a relaxed, family-friendly atmosphere.
Saturday
Step back in time and discover the fierce females who helped build the Gong. Photo: She Shapes History.
Wicked Women of Wollongong Walking Tour
When: Saturday 2 May, 10 am to noon
Where: Flagstaff Point Lighthouse, Endeavour Drive, Wollongong
Cost: Adult $60 | Child $40 | Book via Australian Heritage Festival.
As part of the Australian Heritage Festival, this guided walking tour weaves through the city’s landmarks and hidden laneways to share stories of hotel heiresses, barrier-breaking athletes and creative pioneers. It is a fascinating deep dive into the courage and creativity that shaped our local history, proving that the city’s heritage is far more colourful than the history books often suggest. Comfortable shoes are a must as you meet the “wicked” women who carved out their own space in Wollongong’s past.
Dust off your Akubra because a brand-new country music experience is galloping into Dapto. Image: Stomping Groundz.
Stomping Groundz
When: Saturday 2 May, noon to 11 pm
Where: The Groundz, 89-99 Princes Highway, Dapto
Cost: Child $40.80 | Adult $124.45 | VIP Main Stage $236.65 | VIP Main Bar $257.05 | Book via LocalTix.
Stomping Groundz is set to transform the local showgrounds into a haven for fans of twang and rhythm, featuring a heavy-hitting line-up of national award-winning artists alongside the best homegrown talent the Illawarra has to offer. This isn’t just a concert, it’s a full-blown celebration of country culture with multiple attractions and food stalls running late into the night. It’s a fresh, high-energy take on the traditional music festival, designed to get your boots moving and the community spirit soaring.
Sunday
The scent of freshly roasted chestnuts is in the air as one of the region’s most beloved cultural festivals returns. Image: Fraternity Club Fairy Meadow.
Castagne Day
When: Sunday 3 May, 10 am to 4 pm
Where: The Fraternity Club, 11 Bourke Street, Fairy Meadow
Cost: Free Entry | Ride Wristband Prepaid $25 | Ride Wristband Upon Entry $35 | Book via Fraternity Club.
Castagne Day is a vibrant celebration of Italian tradition, offering a feast for the senses with international food stalls, live music and market treasures. While the adults indulge in authentic flavours and festive atmosphere, the kids can go wild on the carnival rides. It is a quintessential Fairy Meadow Sunday that brings the whole community together to celebrate heritage, family and, most importantly, delicious food. Entry is free, making it the perfect low-stress outing for a sunny afternoon.
Wollongong gets its own taste of Eurovision glitter in this high-octane karaoke competition with a cause. Image: Dr Danielle Camer.
EuroGong Song Contest 2026
When: Sunday 3 May, 1 to 5 pm
Where: Harp Hotel, 124 Corrimal Street, Wollongong
Cost: Spectator $5 | Entrant $30 | Book via Humanitix.
Whether you’re channelling your inner Swedish pop star or going for a dramatic ballad, the EuroGong stage is open for anyone brave enough to grab the mic. With a $500 cash prize on the line and plenty of sequins in the crowd, the atmosphere at the Harp Hotel will be electric. All proceeds go toward Cancer Council NSW, so you can enjoy the campy costumes and sensational vocals knowing your afternoon of entertainment is helping make a real difference in the community.
Thursday
Slow things down and tap into your creative side with an evening of sketching at the library. Image: Shellharbour City Libraries.
Art After Hours: Botanical Illustration
When: Thursday 7 May, 6 to 7 pm
Where: Shellharbour City Library, 76 Cygnet Avenue, Shellharbour City Centre
Cost: $5 | Book via Shellharbour Libraries.
Led by local artist Louise, this hands-on workshop focuses on the intricate world of botanical illustration using simple pencils. You’ll learn about the history of the medium and practise drawing exercises before creating your own leafy masterpiece to take home. It’s a calm, meditative way to spend a Thursday evening, proving that you don’t need a massive budget to pick up a new skill. At just five dollars, it’s the best-value artistic escape in the Illawarra.
