Ten years of The Classics. A huge weekend in the Southern Highlands. And more than $9,800 worth of prizes up for grabs…yep, we’re celebrating BIG at the 2026 Bowral Classic. 🎉
Registered riders will have the chance to win one of 10 prizes at our huge Event Village giveaway, kicking off from 2pm on Saturday 17 October at Loseby Park.
And there are some seriously good prizes up for grabs.
Think a Cervélo Soloist Bike Frame valued at $5,900, a JetBlack Victory Smart Trainer + six months of Zwift, a custom cycling kit from Bowy Active, a cocktail class for four at MillSheds Distillery & Bar, a $500 Lucette Bistro voucher thanks to Duncan Hill Property, a Bendooley Estate voucher, plus plenty more.
Basically, if you were looking for another reason to get excited about Bowral weekend… here it is.
But, it’s not all about the bike…
One of the best things about coming to Bowral Classic? You’re already in one of the prettiest parts of NSW. So why not make a weekend of it?
Come down early, grab a coffee, explore the shops, check out the local food and wine scene, wander through the Event Village and soak up a little Southern Highlands goodness before Sunday’s ride. And this year, the giveaway itself is giving you a pretty good excuse to explore.
We’ve got local experiences and goodies from some of the businesses that make Bowral and the Southern Highlands such a great place to visit, including MillSheds Distillery & Bar, Lucette Bistro thanks to Duncan Hill Property, Bendooley Estate and a Bowral Eats Prize Pack featuring start-line favourite Janeks.
So you could come for the cycling… and leave already planning your next Southern Highlands visit. Not a bad result.
So, what’s up for grabs and how can you win?
There are 10 prizes up for grabs, with a total prize pool worth more than $9,800.
Here’s what you could take home:
🚴 Cervélo Soloist Bike Frame valued at $5,900
⚡ JetBlack Victory Smart Trainer + 6 Months Zwift valued at $930
🚴♀️ Custom Cycling Kit from Bowy Active valued at $375
🍸 Cocktail Class for 4 at MillSheds Distillery & Bar valued at $400
☕ $500 Lucette Bistro Voucher thanks to Duncan Hill Property
🍷 Bendooley Estate Voucher valued at $500
📱 iGPSPORT BSC300T Bike Computer + SR Mini Bike Radar valued at $398
🚗 Allen Smart Suction Go valued at $400
🥟 Bowral Eats Prize Pack including a $100 Janeks voucher and Dumpling Cheers goodies
🚴 2027 Mudgee Classic Gran Fondo Entry valued at $305
If you’re registered for the 2026 Bowral Classic, you’re already in the running! When you collect your registration kit at the Event Village, you’ll receive a coloured ticket tab with a unique number. Keep hold of it, because that little piece of paper could be worth a whole lot more than you think.
The giveaway kicks off from 2pm on Saturday 17 October at the Event Village at Loseby Park, with winners drawn throughout the afternoon.
And there’s one very important rule: you need to be there when your number is called! … (if you’re in a hurry, pass it onto a mate to double their luck! just make sure they’re registered too.)
So grab your registration kit, stick around the Event Village, check out what’s happening, grab yourself a coffee (or something stronger), and keep an ear out for those winning numbers.
Oh and if you’re yet to secure your spot, registrations are still open. We can’t wait to see you in Bowral!