The Bowral Classic returns on Sunday, 18 October 2026, marking a decade of The Classics series and celebrating Australian-owned, proudly run Gran Fondo cycling. Early Bird registrations are now open, inviting riders of all levels to be part of this milestone edition.
Since its inaugural ride in 2016, the Bowral Classic has grown into one of Australia’s most loved Gran Fondo cycling events, attracting thousands of riders to the stunning Southern Highlands each year. The 2026 event promises another unforgettable day in the saddle as riders take on some of the region’s most picturesque roads.
Three Iconic Courses Through the Southern Highlands
The 2026 Bowral Classic offers three challenging and scenic courses ranging from 85km to 150km. Starting on Bong Bong Street in the heart of Bowral, riders will experience the breathtaking landscapes, rolling hills and picturesque towns that have made this event a highlight on the national cycling calendar.
Whether tackling the longer challenge or enjoying the shorter distance, participants can expect fully resourced rest stops, on-course support and a welcoming finish-line celebration.
At the end of the ride, the Event Village at Loseby Park will come alive with live music, gourmet food stalls, local beer and wine bars, and a showcase of Australia’s leading cycling brands.
Celebrating 10 Years of The Classics
“As we celebrate 10 years of The Bowral Classic, we extend our heartfelt thanks to our incredible riders, our passionate community, and our valued commercial partners. Your unwavering support, energy and belief in this event have shaped it into the iconic ride it is today. Together, you’ve built more than a cycling event — you’ve created a tradition that continues to inspire and bring people together year after year.” said James Yaffa, Founder of The Classics.
Each year the Bowral Classic attracts thousands of cyclists from across Australia and overseas, contributing more than $3 million annually to the local tourism economy.
“Events like the Bowral Classic bring thousands of riders and supporters to the Southern Highlands, many of whom stay for the weekend and explore our towns, cafés, wineries and local businesses. It’s a fantastic showcase of our region and delivers a real boost to the local economy while sharing the beauty of the Highlands with visitors from across the country.” said Jesse Fitzpatrick, Mayor of the Wingecarribee Shire Council.
Judy Hannan MP also welcomed riders and supporters to the region.
“I am delighted to welcome ride entrants, volunteers, riders’ families and friends to picturesque Bowral and the surrounding towns and villages in the Southern Highlands. This year’s event is extra special – celebrating 10 years since the inaugural Bowral Classic, Australian Premier Cycling Gran Fondo event in 2016.
The Classic is not and event for riders with challenging hill climbs. The Classic is about charitable causes, promotes physical fitness, promotes overnight tourist accommodation stays and economic spend along the race routes. Also, the Bowral Classic Event Village at the Finish Line in Loseby Park, Bowral will showcase a variety of local businesses. Please support local businesses during your stay at the Bowral Classic.”
Locals are encouraged to get involved by riding, volunteering or joining the weekend celebrations.
Ride & Raise for Charity
The Bowral Classic offers riders the opportunity to support a cause close to their heart. Participants can choose to fundraise for any charity of their choice.
Over the past decade, The Classics events have collectively raised more than $500,000 for charities across Australia.
Early Bird Entries Now Open
Riders can now take advantage of the Early Bird offer, saving on entry fees and securing the official event jersey at a discounted price.
Early Bird registrations close Sunday, 21 June 2026.