Mike O'Connor
As the Bowral Classic prepares to celebrate its 10th anniversary, we meet the riders who have helped make the Southern Highlands event such a fixture on Australia’s cycling calendar.
In 2016, the first Bowral Classic sent riders out onto the roads of the Southern Highlands. A decade later, the event has become one of Australia’s best-known gran fondos, drawing thousands of riders to Bowral for a weekend that combines challenging roads, spectacular scenery and, perhaps most importantly, a huge sense of community.
The 10th Bowral Classic, on 18 October 2026, is therefore more than another edition of the event. It’s a chance to celebrate everything that has made The Classics special over the past decade – and the people who have been part of that story.
To mark the milestone, we spoke to the Bowral Classic ambassadors about their memories of the event, what keeps them returning, their favourite sections of the course and what makes Bowral different from the countless other rides on the cycling calendar.
Some have ridden the event just a handful of times. Others have been there virtually from the beginning. Their answers reveal a common thread: while the climbs, scenery and challenge matter, it’s the people and atmosphere that keep bringing riders back.
Jay Gaffey: “The sense of community”
Describe the Bowral Classic in three words.
Community. Social. Challenging.
Your Classics tally? What keeps you coming back?
I’ve ridden between six to seven Classics now – I’ve honestly lost count!
What keeps me coming back is the incredible atmosphere and sense of community. The Classics have created something really special, and the friendships and connections you make through cycling last well beyond the event itself.
What’s your favourite climb, descent or stretch of road?
Without question, the Athletes Village.
It is the best I’ve experienced anywhere in the world, and I’ve ridden and competed internationally.
Knowing that little treat is waiting for you at the end of the ride keeps you positive when the legs start to complain!
What’s your go-to training session?
I train with a coach, and I think the key is not relying solely on volume but focusing on quality.
My training is a mix of threshold and sweet spot sessions, along with some longer rides.
And hill repeats? I know they work – but I wouldn’t necessarily say I love them!
Finish this sentence: “The Bowral Classic is…”
The Bowral Classic is where community, fun and a genuinely challenging ride come together.
What first got you into cycling?
I always used a bike to commute, but the first time I put on cleats and lycra was for a charity ride for Tour de Cure.
That was really the moment cycling became something more than just a way of getting from A to B – and I was hooked.
When you’re not on the bike, what would we find you doing?
I’m on the committee of the Dementia Research Community, so I spend a lot of time involved in fundraising and helping bring people together around dementia research.
Cycling has played a huge role in building community in my own life, and I see that same power in The Classics. The friendships and connections you make through cycling are incredibly special.
What’s one thing people might be surprised to learn about you?
I recently rode for 45 hours continuously on an indoor trainer – one hour for every 10,000 Australians living with dementia – to raise awareness and funds for dementia research.
So perhaps the surprising thing is that I don’t always make the most sensible decisions!
What are you most looking forward to this October?
Celebrating The Classics with my friends and the wider cycling community.
I think what makes the event so special is the way it brings cycling to the broader Australian public – families and friends can all be involved – while still providing a genuinely tough challenge for experienced riders who want to push themselves.
I’m really looking forward to celebrating that balance, and the 10-year milestone, with everyone.
What advice would you give first-time riders?
Enjoy the whole experience and don’t underestimate the course!
Take in the atmosphere, enjoy the community and soak up the day. And remember – the Athletes Village is waiting for you at the end, so keep pedalling!
Kate Lee: “It’s a vibe”
Describe the Bowral Classic in three words.
Challenging, vibrant, fun.
Your Classics tally? What keeps you coming back?
This will be my second official Bowral Classic – third if you count the unofficial Bowral Classic of 2025! – and I’ve done one Mudgee Classic.
I love the community that the event brings together, having a goal to work towards and having a great excuse for a weekend away with mates!
What’s your favourite part of the course?
The final descent home – it means all the climbing is done, plus it’s a very fun and fast descent if you know it!
What’s your go-to training session?
VO2 max intervals, endurance rides, sweet spot training.
Finish this sentence: “The Bowral Classic is…”
A vibe.
What first got you into cycling?
I was unfit, unhealthy and overweight!
I joined an indoor cycling gym and set a goal of going twice a week. They had little power leaderboards at the end of the class and I became quite competitive.
One day, the instructor asked if I’d ever go road cycling with her, so I got a bike on Marketplace, bought some kit on the way to my first-ever ride, crashed on my first-ever ride, and became addicted.
The rest is history.
When you’re not on the bike, what would we find you doing?
A job that wasn’t actually on my to-do list for the day, when I should be doing another half-finished job!
What’s one thing people might be surprised to learn about you?
Cycling related? I doubt myself a lot and get in my head that I won’t be good enough or I won’t be able to do something, particularly in racing.
Non-cycling related? I have toe thumbs! Same as Megan Fox!
What are you most looking forward to this October?
I am really hoping that my partner, Owen, and my mate and fellow Classics ambassador, Aidan Burgess, can line up a tandem bike to ride the event on.
I would love to see the party bike dream come alive – and also watch them suffer!
And also seeing everyone come together to ride bikes in a different part of the world.
What advice would you give first-time riders?
Charge your Di2/SRAM!
Pack and eat more food during the event than you think. It’s always good to have more than less!
And have fun. Set a big, outrageous goal and go after it – what’s the worst that can happen!? Literally.
JA Hazlett: “Smiles. Suffering. Satisfaction”
Describe the Bowral Classic in three words.
Smiles. Suffering. Satisfaction.
Your Classics tally? What keeps you coming back?
I’ve lost count!
For me it’s become part of the cycling calendar. I usually try to go back to Northern Ireland for “summer”, so Bowral is always one of the first big rides after I return to Australia.
It’s a chance to catch up with friends, in a beautiful place that kind of looks a bit like Ireland. It’s not far from Sydney and it’s always a fun weekend away.
What’s your favourite climb, descent or stretch of road?
Every descent and the stretch to the finish line so I can get a cider!
It’s a great course and can be as challenging or chilled as you want it to be. After fracturing the neck of my femur in an off-road bike accident earlier this year, I think it will be more of a chilled ride for me this year.
What’s your go-to training session?
As I mentioned above, I will most likely be back in Northern Ireland before Bowral so training will probably be in the Sperrin Mountains and maybe a lap of Lough Neagh before I come back to Sydney for Bobbin Head and Akuna repeats.
Hill repeats? I can’t say I love any hills really but they do have a purpose and definitely help for courses like Bowral.
Finish this sentence: “The Bowral Classic is…”
…hard enough to make you question your life choices, good enough to make you enter again.
What first got you into cycling?
A relationship breakup got me into triathlons. I figured if I could survive those, I could survive most things.
One challenge led to another, eventually taking me to compete in the Race Across America, Race Around Ireland and riding every stage of the Tour de France ahead of the men to campaign for the return of the Women’s Tour de France.
Being there with the Zwift team in 2022 to see it return and leading a group of riders around Paris before the start is still one of the proudest moments of my cycling journey.
When you’re not on the bike, what would we find you doing?
Working to fund my adventures, catching up with friends, hiking, swimming or kayaking.
What’s one thing people might be surprised to learn about you?
I still love to go clubbing from time to time – as long as I’m home before midnight. Cinderella set a good example!
What are you most looking forward to this October?
Seeing familiar faces.
Cycling has introduced me to many friends across Australia and around the world. Bowral is a great place to catch up with lots of people in one spot and enjoy the pretty village and atmosphere.
What advice would you give first-time riders?
Enjoy the whole day. Take photos. Chat to people you’ve never met.
Eat before you’re hungry, drink before you’re thirsty and remember why you signed up in the first place.
The fastest riders don’t always have the best stories at events like these. Hang around in the village at the end and soak up the atmosphere.
Giles Bourne: Ten Bowrals and counting
Describe the Bowral Classic in three words.
Beautiful, painful, worth it.
Your Classics tally? What keeps you coming back?
I’ve done it every single year since it started.
I’ll admit I’m getting progressively slower each year, but I’m choosing to file that under “wisdom” rather than “decline.”
I keep coming back because it’s genuinely one of the best events in Australia, and I’ve done a lot of them. Best atmosphere, most scenic ride, hands down.
What’s your favourite climb, descent or stretch of road?
Officially, I’ll say the Gibraltar climb.
Unofficially, that’s a complete lie. It used to be my favourite and now it’s my nemesis. Whoever decided to put it at the end of the ride clearly did so purely to mess with my mind, and honestly, it’s working.
What’s your go-to training session?
The training plan was going brilliantly, right up until I decided to fall down a hill trail running in Derbyshire and break my ribs.
Turns out running downhill and staying upright are two separate skills, and I’d only trained for one of them.
Finish this sentence: “The Bowral Classic is…”
I think the Bowral Classic is one of the must-do rides in Australia.
What first got you into cycling?
I got into cycling growing up in rural England, where a bike wasn’t a lifestyle choice, it was the only way to go see your mates in the next village.
This led to various cycling trips in our teens in the summer, starting with the Isle of Wight and then a circumnavigation of the Channel Islands, leading on to a trip down the Loire Valley.
Steel-framed bikes, everything crammed into panniers, riding in jeans – no Lycra in sight!
When you’re not on the bike, what would we find you doing?
Working far too hard!
I run a venture investing business and I also sit on a few boards, which between them do an excellent job of eating up all the time I should be spending running and riding.
What’s one thing people might be surprised to learn about you?
Before I got properly into cycling, I used to fly aeroplanes.
Great hobby, but it did absolutely nothing for my fitness!
What are you most looking forward to this October?
Looking forward to being back for the 10th anniversary with a good contingent from the High Street Flyers, who’ve been long-term supporters of the event.
What advice would you give first-time riders?
Why wouldn’t you want to do this?
It’s one of the best events out there, spectacular scenery, and really – it’s just a cruisy day out in the countryside.
The Gibraltar climb at the end notwithstanding.
Fancy joining them? The 2026 Bowral Classic is open for entries now.
Look out for part two next week.
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.
