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
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...
Jimeoin - Ballyhoo
12 Sep 2026
Catch Jimeoin for his unique blend of observational humour, physical expressiven...
Horizontal Festival 2026
2 Oct 2026
3 Oct 2026
3 Oct 2026
4 Oct 2026
Food, Wine & Music Festival in the VineyardsOCTOBER LONG WEEKEND 2026 Set am...
Bowral Classic 2026 - Australia's Premier Cycling Gran Fondo
18 Oct 2026
The Bowral Classic returns on Sunday, 18 October 2026, marking a...
Bundanoon Folk Festival 2026
20 Nov - 22 Nov 2026
Welcome to the Bundanoon Folk Festival to be held on Gundungurra country in the...
Bundanoon Highland Gathering - Brigadoon 2027
3 Apr 2027
The next Annual Highlands Gathering will take place on Saturday 3 April 2027 A f...