The Southern Highlands is full of exciting events year-round.
From the Tulip Time Festival, Brigadoon to Bong Bong Races and everything in between, there is always something on in the Southern Highlands to entertain and inspire.
Key Events
Sydney Comedy Festival Showcase
21 May 2026
The Sydney Comedy Festival Showcase Tour will be tearing up the freeways of Aust...
2026 Melbourne International Comedy Festival Roadshow
20 Jun 2026
Australia’s biggest comedy festival is hitting the road and bringing the laughs...
Marty Sheargold - The Red Card Tour
28 Aug 2026
As much as I’ve been trying to embrace early retirement – I’m bored shitless so...
An Evening with Anna Funder
10 Sep 2026
Oxley College presents: As a writer who places being human at the centre of her...
Horizontal Festival 2026
2 Oct 2026
3 Oct 2026
3 Oct 2026
4 Oct 2026
Food, Wine & Music Festival in the VineyardsOCT LONG WEEKEND 2026 Set among...
Bowral Classic 2026 - AUSTRALIA’S PREMIER CYCLING GRAN FONDO
18 Oct 2026
The Bowral Classic returns on Sunday, 18 October 2026, marking a...