Mike O'Connor
The Bowral Classic is turning 10, and the milestone celebration is set to be bigger than ever, with a huge weekend of riding, local experiences and more than $9,800 worth of prizes up for grabs at the 2026 event.
To mark a decade of The Classics, registered riders will have the chance to win one of 10 prizes worth more than $9,800, with the giveaway taking place at the Bowral Classic Event Village at Loseby Park from 2pm on Saturday 17 October.
The prize pool includes some serious cycling prizes, including a Cervélo Soloist Bike Frame valued at $5,900, a JetBlack Victory Smart Trainer plus six months of Zwift, and a custom cycling kit from Bowy Active.
But it’s not all about the bike. The giveaway also shines the spotlight on some of the Southern Highlands’ local businesses and experiences, giving riders even more reason to explore beyond the Event Village.
From a cocktail class for four at MillSheds Distillery & Bar in Bowral and a $500 Lucette Bistro voucher thanks to Duncan Hill Property, to a Bendooley Estate voucher and a Bowral Eats Prize Pack featuring start-line favourite Janeks, there’s plenty on offer.
For riders travelling from Sydney, Canberra and beyond, the Bowral Classic is an opportunity to turn a day on the bike into a full Southern Highlands getaway.
With the Event Village running across Saturday and Sunday, visitors can arrive early, explore Bowral, discover local cafés, restaurants and cellar doors, and soak up the atmosphere before the bikes roll out on Sunday morning.
The weekend also provides an opportunity for local businesses to welcome thousands of visitors into the region, showcasing the food, hospitality, scenery and experiences that make the Southern Highlands a go-to.
Your Ride Awaits
With three courses to choose from, cyclists can take on the Maxi Classic, Challenge Classic or Rouleurs Classic and experience the Southern Highlands from the saddle.
Whether it’s a big day in the hills, a challenge with your mates or a more social spin through the region, there’s a ride for everyone.
Entries are still open for the 2026 Bowral Classic, with riders invited to join the 10th anniversary celebrations this October.
So, round up your crew, choose your course and get ready for a milestone weekend of cycling, community and everything the Southern Highlands has to offer.
Mike O’Connor – A keen cyclist, runner and photographer, Mike O’Connor is the Editor of Bicycling Australia. He manages the BA website and social media, and loves promoting the achievements of Australian cyclists.
