More than 4,000 people flocked to the picturesque Crooked River Estate in Gerringong over the weekend for the Winter Wine Festival, making it the event’s biggest year yet.

Held over two days, the festival featured a standout musical lineup, with Xavier Rudd and The Beautiful Girls headlining Saturday, and Boy & Bear and Meg Mac closing out Sunday’s festivities.

Event photographer Lisa O’Connell described the atmosphere as “electric.”

“This year's Winter Wine Festival at Crooked River Wines delivered a weekend to remember,” O’Connell said.

“The South Coast has produced some amazing talent, and it was fantastic to see Kiama’s Surely Shirley alongside Illawarra locals like Kane Calcite and Cheeky Leash - whose awesome set even included flying monkeys taking the stage.” 

“I’m sure Boy & Bear’s Feeding Line and Xavier’s Follow The Sun could be heard all across Gerringong with the crowd singing along.”

Some of the 4000 people who attended the Winter Wine Festival over the weekend. Photo: Lisa O’Connell @daughter_of_the_revolution 

The 2025 festival marks the fifth edition since the event was revived in 2021, and Crooked River Estate Managing Director Roger Lloyd confirmed this year was their biggest yet.

“This was one of our best events in terms of the weather and the bands,” said Lloyd.

“We partnered with Yours and Owls this year to help with the lineup, and that collaboration worked really well.”

The festival also served as the perfect opportunity to unveil Crooked River Estate’s brand-new on-site wedding venue, which doubled as a bar for the weekend.

“We’ve only just completed that space and used it as one of the bars. The feedback was overwhelmingly positive - people were genuinely awestruck. We’re really proud of how it turned out,” Lloyd said.

The Winter Wine Festival capped off a packed weekend of community events across the Kiama LGA, showcasing the region’s thriving live music scene, vibrant culture, and community spirit.