One of the Southern Highlands' biggest days on two wheels is back for a milestone year. The Bowral Classic returns on Sunday, 18 October 2026, marking a decade of what's become one of Australia's most-loved Gran Fondo cycling events — and if you're planning to line up on Bong Bong Street, now's the time to start thinking about your gear.
The Basics: Dates, Location, Courses
The 2026 Bowral Classic offers three routes through the rolling hills and scenic country roads of the Southern Highlands:
- 150km Maxi Classic — through Berrima, Moss Vale, Bundanoon, Robertson and Glenquarry, with three King/Queen of the Mountain climbs including a sharp finish over Gibraltar Hill.
- 120km Challenge Classic — follows the Maxi route before tackling the Oxleys Hill climb, a 1.3km sharp ascent with 129m of elevation gain.
- 85km Rouleurs Classic — a shorter, still scenic option through the same beautiful countryside.
All three courses start on Bong Bong Street in the heart of Bowral and finish at Loseby Park, where the Event Village comes alive with live music, food trucks, and a showcase of Australian cycling brands.
A Decade of the Bowral Classic
Since its first edition in 2016, the Bowral Classic has grown into a genuine fixture on the national cycling calendar, drawing thousands of riders from across Australia and overseas each year and contributing an estimated $3 million annually to the local Southern Highlands economy. To mark ten years, organisers have released a limited-edition anniversary jersey and cap for early registrants.
What to Know Before You Register
- Rider insurance is compulsory — a $10 fee applies if you're not already covered through an insurer like AusCycling.
- Riders aged 12–16 need an AusCycling Race Licence and must ride with an accompanying adult.
- Aero bars and TT bars are not permitted on any course.
- E-bikes are allowed across all events, provided they meet NSW e-bike regulations — and it's on you to make sure your battery lasts the distance you've chosen.
Getting Your Gear Ready for 150km (or 85km)
Whichever distance you're tackling, a long day in the Southern Highlands saddle rewards a bit of preparation. Here's what's worth checking off your list before October.
Nutrition and Hydration Storage
With rest stops spaced out across 85–150km, having quick access to gels, bars and a spare tube matters. A top tube or saddle bag keeps everything within reach without digging through jersey pockets mid-climb.
Know the Climbs Before You Hit Them
Gibraltar Hill and Oxleys Hill aren't the kind of climbs you want to discover cold. A GPS computer with route navigation loaded ahead of time helps you pace effort against what's coming, rather than guessing.
Comfort Over Distance
Whether you're riding 85km or the full 150km Maxi, padded shorts and a well-fitted saddle bag make a real difference by the final descent into Loseby Park.
Frequently Asked Questions
When is the Bowral Classic 2026?
Sunday, 18 October 2026, in Bowral, NSW — the event's 10th anniversary edition.
What course distances are available?
150km Maxi Classic, 120km Challenge Classic, or 85km Rouleurs Classic, all starting and finishing in Bowral.
Is insurance required?
Yes, rider insurance is compulsory, with a $10 fee if you're not already covered.
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