From live music and local artists to workshops that’ll have you picking up a new hobby
If you’re looking to mix up your usual plans this May, the Shire’s creative scene is delivering in all the right ways. From live music popping up across local venues to hands-on workshops and festivals, there’s a steady lineup of art, culture and experiences worth stepping out for! Whether you’re into jazz, local makers or something a little different, this month is the perfect time to tap into it.
Great Southern Nights

Great Southern Nights is back, bringing a stacked run of live music to venues across the Shire this May.
The statewide series sees over 300 gigs roll out across more than 200 venues, with a mix of established names and emerging artists across everything from indie and rock to pop and R&B. Across the Shire, expect local venues from Cronulla to Engadine to get involved, with free live shows to catch. This is one to keep an eye on. Check out the gig guide.
Bundeena Maianbar Art Trail

Tucked along the edges of the Royal National Park, the Bundeena Maianbar Art Trail offers a more relaxed way to experience the Shire’s creative community.
Held on the first Sunday of each month, the trail invites you to explore a collection of working studios, galleries and pop-up exhibition spaces, all set within one of the area’s most scenic pockets. Expect a mix of painting, ceramics, photography and handmade works, alongside the chance to meet the artists behind them.
Natalie Claire Jazz Band

If jazz is your thing, this one’s worth locking in. Natalie Claire is bringing a full night of classic jazz done right on Saturday, the 9th of May at The Sutherland Pavilion, celebrating the likes of Ella Fitzgerald, Nina Simone and Frank Sinatra, backed by a seriously talented band. Expect tender ballads, hard-swinging jazz and upbeat Latin rhythms throughout.
With Mother’s Day just around the corner, it’s a simple way to plan something a little different. Insider scoop: For 15% off tickets, use code MUM15.
Hazelhurst Arts Fest

Hazelhurst Arts Fest returns on Sunday, the 17th of May, bringing a full day of art, live music and hands-on workshops to one of the Shire’s go-to creative spaces. Explore a range of exhibitions, catch live performances and take part in hands-on workshops, all set across the gallery and surrounding gardens. With a mix of emerging and established artists, there’s something new for the whole family to discover. Arrive hungry and be sure to check out Hazel Cafe and Bar whilst you’re there.
Engadine Autumn Festival

Engadine Autumn Festival is making its debut this May, bringing a full lineup of live music and local performances to Cooper Street Reserve. Running across Saturday 23rd and Sunday 24th of May from 9:00am to 3:00pm, expect everything from live bands to community acts taking over the stage across both days. Alongside the music, there’ll be market stalls, food, rides and plenty for the kids, making it an easy, family-friendly day out!
Cronulla Jazz and Blues Festival

Rounding out the month, the Cronulla Jazz and Blues Festival returns on Wednesday, the 27th of May, transforming Cronulla into a multi-day celebration of live music. Spanning across five days and over 20 stages, expect a mix of jazz, blues and everything in between, with performances popping up across local parks, venues and open-air spaces throughout Cronulla’s coastal backdrop. Alongside the music, there’s bars, food and markets stalls, family-friendly programming, a Film Festival, Record Fair and the Blues Awards Night. With plenty going on for all ages, this is one to have on your radar this May. Check out the performance schedule.