Mike O'Connor
The Bowral Classic celebrated its 10th anniversary in style on Sunday, 18 October, with more than 2,500 riders taking to the roads of the Southern Highlands and more than $130,000 raised for charity.
Riders lined up on Bong Bong Street in Bowral to tackle three distances: the 150km Maxi Classic, 120km Challenge Classic and 85km Rouleurs Classic, taking in the area’s rolling hills, picturesque countryside and country towns.
After a cold start to the weekend, the weather turned around just in time for the main event. Saturday’s celebrations at Loseby Park were met with chilly conditions and some rain, but Sunday’s initially foggy morning soon gave way to sunshine, providing a welcome change for riders heading out across the region.
For many, it was a chance to enjoy a day on the bike with friends and fellow club members, while cycling groups turned out in force. Pastries CC brought more than 110 riders, with Out Of Office Cycling Club fielding 30 and Centennial Park Cycling Club another 26.
The 10th anniversary was also a significant milestone for the event’s charity efforts, with riders, participating charities and the wider community raising more than $130,000 across a range of causes.
Official charity partner Little Legs Foundation raised almost $30,000 to support children and families affected by childhood brain cancer.
“Reaching 10 years of The Classics is something we’re incredibly proud of, but what makes these events truly special is the community behind them,” said The Classics founder James Yaffa.
“It’s about bringing people together through a shared love of cycling, supporting important causes and creating a positive impact in the places we visit. To see more than 2,500 riders out enjoying the Southern Highlands, alongside the incredible fundraising efforts, is a fantastic way to celebrate this milestone.”
The weekend’s success also relied on local volunteers, community groups, businesses and residents, who helped bring the event to life and welcome visitors to the region.
Prizes, crowds and a Cervélo winner
Saturday’s event village at Loseby Park provided a gathering point for riders, families, sponsors and visitors ahead of Sunday’s ride.
One of the highlights was a prize giveaway worth more than $9,800, with 10 prizes awarded to participants. The draw attracted a huge crowd between 2pm and 3pm, with riders needing to be present to claim their prizes.
The biggest prize was a Cervélo Soloist frameset, won by NSW rider Ali P., who was understandably stoked with the result, telling organisers: “I never win anything!”
Hosted by MC Angus Calder, the giveaway featured a barrel draw and plenty of anticipation, with sponsors including our friends at Cervélo taking part in selecting winners. Despite the excitement, organisers needed to redraw just one of the winning tickets.
Since its inaugural edition in 2016, the Bowral Classic has become an established fixture on Australia’s cycling calendar, attracting riders from across NSW, interstate and beyond to experience the Southern Highlands on two wheels.
With its 10th edition now complete, we’re delighted to confirm the event will return on 17 October 2027.
If you were one of the lucky riders on the day, you can check times and placings on the Bowral Classic 2026 results page.
For more information on the event’s fundraising efforts, visit the Bowral Classic charity fundraising page.
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.
